Pursuant to Federal Rule of Appellate Procedure 43 c 2 , Andrew M. Cuomo, New York… v. No. 07-3588-pr 4 5 DALE ARTUS, Superintendent, Clinton Correctional Facility

Pursuant to Federal Rule of Appellate Procedure 43(c)(2), *
Andrew M. Cuomo, New York State Attorney General, is
automatically substituted as respondent-appellee for Elliot L.
Spitzer, former New York State Attorney General.
1
05-4375-pr; 06-3550-pr; 07-1599-pr; 07-3588-pr; 07-3949-pr
Besser v. Walsh; Phillips v. Artus; Portalatin v. Graham; Morris v. Artus;
Washington v. Poole
1 UNITED STATES COURT OF APPEALS
2 FOR THE SECOND CIRCUIT
3 AUGUST TERM, 2007
4 (Argued in Tandem: April 16, 2008 Decided: March 31, 2010)
5 Docket Nos. 05-4375-pr, 06-3550-pr, 07-1599-pr, 07-3588-pr,
6 07-3949-pr
7 (consolidated for disposition)
8 - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -
9
10 JAMES BESSER, a/k/a JAMES ZERILLI,
11 Petitioner-Appellant,
12
13 v. No. 05-4375-pr
14
15 JAMES WALSH, Superintendent, Sullivan Correctional Facility,
16 Respondent-Appellee.
17
18 - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -
19
20 WILLIAM PHILLIPS,
21 Petitioner-Appellant,
22
23 v. No. 06-3550-pr
24
25 DALE ARTUS, Superintendent, Clinton Correctional Facility,
26 and ANDREW M. CUOMO, New York State Attorney General,*
27 Respondents-Appellees.
28
29 - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -
30
31 CARLOS PORTALATIN,
32 Petitioner-Appellee,
33
34 v. No. 07-1599-pr
35
36 HAROLD GRAHAM, Superintendent, Auburn Correctional Facility,
37 Respondent-Appellant.
38
39 - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -

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** Pursuant to Federal Rule of Appellate Procedure 43(c)(2),
Andrew M. Cuomo, New York State Attorney General, is
automatically substituted as respondent-appellee for Elliot L.
Spitzer, former New York State Attorney General.
*** The Clerk of the Court is directed to amend the official
caption in these cases to conform to the listing of the parties
above.
**** The Honorable J. Garvan Murtha, United States District
Judge for the District of Vermont, sitting by designation.
2
VANCE MORRIS, 1 Petitioner-Appellant, 2
3 v. No. 07-3588-pr 4
5 DALE ARTUS, Superintendent, Clinton Correctional Facility, and 6 ANDREW M. CUOMO, New York State Attorney General, **
7 Respondents-Appellees. 8
9 - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 10
11 WILLIAM WASHINGTON, 12 Petitioner-Appellee, 13
14 v. No. 07-3949-pr 15
16 THOMAS POOLE, Superintendent, Five Points Correctional Facility, 17 Respondent-Appellant.***
18
19 - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 20
21 B e f o r e: WINTER, SACK, Circuit Judges and MURTHA, District 22
Judge.****
23
Five New York prisoners, sentenced under New York’s 24
persistent offender statute, petitioned for a writ of habeas 25
corpus. We hold principally that the New York courts’ upholding 26
of the constitutionality of the New York state persistent felony 27
offender statute after the United States Supreme Court’s decision 28
in Blakely v. Washington, 542 U.S. 296 (2004), was an 29
unreasonable application of clearly established Sixth and 30

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3
Fourteenth Amendment law. 1
RICHARD M. GREENBERG, Office of the 2 Appellate Defender, New York, New York, 3 for Petitioner-Appellant Besser. 4
5 MARTIN M. LUCENTE, The Legal Aid 6 Society, Criminal Appeals Bureau, New 7 York, New York, for Petitioner-Appellant 8 Phillips. 9
10 JOSHUA MICHAEL LEVINE (Lynne W.L. 11 Fahey), Appellate Advocates, New York, 12 New York, for Petitioner-Appellee 13 Portalatin. 14
15 ANDREW C. FINE (Paul Wiener), The Legal 16 Aid Society, Criminal Appeals Bureau, 17 New York, New York, for Petitioner- 18 Appellant Morris. 19
20 JONATHAN M. KIRSHBAUM (Robert S. Dean), 21 Center For Appellate Litigation, New 22 York, New York, for Petitioner-Appellee 23 Washington. 24
25 MARK DWYER, Assistant District Attorney, 26 of counsel (Robert M. Morgenthau, 27 District Attorney, New York County; 28 Morrie I. Kleinbart, Special Assistant 29 District Attorney; Nicole Beder, 30 Assistant District Attorney, of 31 counsel), New York, New York, for 32 Respondent-Appellee Walsh. 33
34 ROSEANN B. MACKECHNIE, Deputy Solicitor 35 General for Criminal Matters (Andrew M. 36 Cuomo, Attorney General of the State of 37 New York; Barbara D. Underwood, 38 Solicitor General; Malancha Chanda, 39 Assistant Attorney General, of counsel), 40 New York, New York, for Respondents- 41 Appellees Artus and Cuomo. 42
43 LEONARD JOBLOVE, Assistant District 44 Attorney, of counsel (Charles J. Hynes, 45 District Attorney, Kings County; Ann 46 Bordley, Assistant District Attorney, of 47 counsel), Brooklyn, New York, for 48 Respondent-Appellant Graham. 49
50
51

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4
Andrew M. Cuomo, Attorney General of the 1 State of New York (Barbara D. Underwood, 2 Solicitor General; Roseann B. 3 MacKechnie, Deputy Solicitor General for 4 Criminal Matters; Malancha Chanda, 5 Assistant Attorney General, of counsel), 6 New York, New York, for Respondent- 7 Appellant Poole. 8
9 Marshall A. Mintz, Mintz & Oppenheim 10 LLP, New York, New York (Richard D. 11 Willstatter, Chair of the Amicus Curiae 12 Committee of the New York State 13 Association of Criminal Defense Lawyers, 14 Vice-Chair of the 2nd Circuit Amicus 15 Curiae Committee of the National 16 Association of Criminal Defense Lawyers, 17 White Plains, New York), for Amici 18 Curiae New York State Association of 19 Criminal Defense Lawyers and National 20 Association of Criminal Defense Lawyers. 21
22
WINTER, Circuit Judge: 23
The principal question on appeal is whether New York state 24
court decisions affirming sentences enhanced under New York’s 25
persistent felony offender (“PFO”) statute, N.Y. Penal Law § 26
70.10, unreasonably applied clearly established federal law. 28 27
U.S.C. § 2254(d). 28
The district court issued a writ of habeas corpus in the 29
petitions of Carlos Portalatin and William Washington and the 30
relevant state authorities brought this appeal. 1 See Washington 31
v. Poole, 507 F. Supp. 2d 342, 344 (S.D.N.Y. 2007) (Koeltl, J.); 32
Portalatin v. Graham, 478 F. Supp. 2d 385, 386 (E.D.N.Y. 2007) 33
(Gleeson, J.). The district court declined to issue the writ in 34
the petitions of James Besser, William Phillips, and Vance 35
Morris, who then appealed. See Morris v. Artus, No. 06 Civ. 36
4095(RKS), 2007 WL 2200699, at *1 (S.D.N.Y. July 30, 2007) 37

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5
(Sweet, J.); Phillips v. Artus, No. 05 Civ. 7974(PAC), 2006 WL 1
1867386, at *1 (S.D.N.Y. June 30, 2006) (Crotty, J.); Besser v. 2
Walsh, No. 02 Civ. 6775(LAK), 2005 WL 1489141, at *1 (S.D.N.Y. 3
June 22, 2005) (Kaplan, J.). Because these five appeals 4
presented substantially similar or overlapping issues, we heard 5
them together. 6
We hold that the Sixth Amendment right to a jury trial, 7
applicable to the states as incorporated by the Fourteenth 8
Amendment, prohibits the type of judicial fact-finding resulting 9
in enhanced sentences under New York’s PFO statute. We also hold 10
that this prohibition was not clearly established until Blakely 11
v. Washington, 542 U.S. 296 (2004). Because Besser’s conviction 12
became final before Blakely issued, the state court decisions 13
upholding his conviction were neither contrary to nor an 14
unreasonable application of clearly established federal law. We 15
therefore affirm the denial of the writ as to Besser. However, 16
because the relevant state court decisions upholding enhanced 17
sentences for Phillips, Morris, Portalatin, and Washington were 18
issued after Blakely, those decisions were not reasonable 19
applications of clearly established law. Nevertheless, we remand 20
these cases to the district court for a determination of whether 21
the error was harmless. 22
BACKGROUND 23
a) The Persistent Felony Offender Statute 24
There are three increasingly harsh levels of sentencing 25
applicable to felony offenders under Article 70 of New York’s 26

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6
penal laws pertinent to this appeal. First-time felony offenders 1
are generally sentenced according to indeterminate ranges based 2
on the class of offense. See N.Y. Penal Law § 70.00. 2 Second 3
felony offenders are subject to enhanced sentences, based solely 4
upon the finding of one qualifying prior felony conviction, again 5
according to the class of offense. See id. § 70.06. Under the 6
PFO statute, a defendant who has been previously convicted of two 7
felonies is a “persistent felony offender” (sometimes “PFO”). 8
See id. § 70.10(1)(a). PFO’s may be sentenced to an 9
indeterminate sentence in the range authorized for Class A-I 10
felony offenders rather than the range authorized for the class 11
of the defendant’s actual offense. See id. § 70.10(2); 3 see also 12
N.Y. Crim. Proc. Law § 400.20(1)(b). Class A-I felonies carry a 13
minimum sentence of 15 years and a maximum of life. 4 See N.Y. 14
Penal Law §§ 70.00(2)(a), 70.00(3)(a)(i). 5
15
The difference in a defendant’s sentencing exposure depends 16
heavily upon which level’s range is applicable. Once classified 17
as a PFO, a defendant may be subject to a minimum sentence 18
exceeding the maximum sentence for second felony offenders 19
applicable to the crime committed. For example, a first-time 20
offender convicted of a Class E felony would be subject to a term 21
of 1 1/3 to 4 years. See id. § 70.00(2)-(3). Were the defendant 22
sentenced for a Class E felony as a second felony offender, he or 23
she would be subject to a term of 1.5 to 4 years. See id. § 24
70.06(3)-(4). The same defendant given the enhanced sentence 25

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7
under the PFO statute would be subject to a term of 15 years to 1
life. See id. §§ 70.00(2)-(3), 70.10(2). 2
Under the provisions applicable to first and second felony 3
offenders, the existence or non-existence of a prior felony alone 4
determines the applicable range. See id. §§ 70.00-70.06. To 5
sentence under the PFO statute, the sentencing court must make a 6
finding of at least two prior felony convictions, rendering that 7
defendant a PFO and exposing him or her to a Class A-I sentence. 8
See id. § 70.10. After making that finding, the court turns to 9
whether “the history and character of the defendant and the 10
nature and circumstances of his criminal conduct” (sometimes 11
“history/character/criminal conduct”), id. § 70.10(2); N.Y. Crim. 12
Proc. Law § 400.20(1), is such that the PFO should, in the public 13
interest, be given a Class A-I sentence. 6 N.Y. Crim. Proc. Law § 14
400.20(1). In making this finding, the court must conduct a 15
hearing at which the prosecution bears the burden of proof and 16
“[m]atters pertaining to the defendant’s history and character 17
and the nature and circumstances of his criminal conduct” must be 18
established by a preponderance of the evidence. Id. § 400.20(5). 19
“Uncontroverted allegations in the statement of the court are 20
deemed evidence in the record.” Id. § 400.20(7). 21
If the sentencing court imposes a Class A-I sentence, “the 22
reasons for the court’s opinion shall be set forth in the 23
record.” N.Y. Penal Law § 70.10(2). The imposition of that 24
enhanced sentence is then subject to two kinds of appellate 25
review. First, an appellate court has the power, in the 26

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8
“interest[s] of justice,” to reduce a Class A-I sentence within 1
the Class A-I range, e.g., from 19 years to life to 15 years to 2
life. See N.Y. Crim. Proc. Law § 470.20(6). Second, an 3
imposition of a Class A-I sentence is subject to an “interest[s] 4
of justice” review and will be “held erroneous as a matter of 5
law, [if] the sentencing court acts arbitrarily or irrationally.” 6
People v. Rivera, 833 N.E.2d 194, 199 (N.Y. 2005). Were 7
imposition of a Class A-I sentence under the PFO statute found by 8
an appellate court to be “arbitrary[]” or “irrational[,]” the 9
court must resentence the defendant or remand for resentencing to 10
a “legally authorized lesser sentence,” N.Y. Crim. Proc. Law § 11
470.20; see also People v. LaSalle, 734 N.E.2d 749, 750 (N.Y. 12
2000) (memorandum decision), usually as a second felony offender 13
or second violent felony offender. See, e.g., People v. 14
Williams, 658 N.Y.S.2d 264, 265 (App. Div. 1997); see also People 15
v. Greene, 871 N.Y.S.2d 323, 325 (App. Div. 2008) (citing 16
Williams, 658 N.Y.S.2d at 265); People v. Truesdale, 845 N.Y.S.2d 17
363, 364-65 (App. Div. 2007); cf. People v. Wilsey, 753 N.Y.S.2d 18
232, 233 (App. Div. 2003); People v. Yale, 373 N.Y.S.2d 901, 904- 19
06 (App. Div. 1975). 20
Because second felony offender status usually exposes a 21
defendant to maximum sentences below the maximum (and often the 22
minimum) of the Class A-I range, serious constitutional issues 23
arise, as discussed infra, and our interpretation of the PFO 24
statute is critical to the constitutional analysis. In the 25
briefs submitted by state authorities, it was suggested that a 26

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9
finding of two felony convictions alone locks in the Class A-I 1
range, with life as a maximum. We disagree. The 2
history/character/criminal conduct findings, which are subject to 3
appellate review, are necessary to lock in the Class A-I range 4
and, if such findings do not justify a Class A-I sentence, 5
require the sentencing court to sentence the defendant in a 6
lesser range, usually as a second felony (or violent felony) 7
offender. 7
8
The state authorities rely for their argument upon language 9
in Rivera. We therefore quote the pertinent portion of that 10
decision at length: 11
[D]efendants are eligible for persistent 12 felony offender sentencing based solely on 13 whether they had two prior felony 14 convictions. Thus, . . . no further findings 15 are required. This conclusion takes 16 defendant’s sentence outside the scope of the 17 violations described in Apprendi and its 18 progeny. 19
20 The [United States] Supreme Court has 21 held that a judge (as opposed to a jury) may 22 find the fact of a defendant’s prior 23 conviction without violating the Sixth 24 Amendment . . . . 25
26 After determining defendant’s status as 27 a persistent felony offender, the [court that 28 sentenced Rivera] went on to consider other 29 facts in weighing whether to impose the 30 authorized persistent felony offender 31 sentence. . . . If, based on all it heard, 32 the [sentencing] court’s view of the facts 33 surrounding defendant’s history and character 34 were different, the court might well have 35 exercised its discretion to impose a less 36 severe sentence. 37
38 Nevertheless, the relevant question 39 under the United States Constitution is not 40 whether those facts were essential to the 41

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trial court’s opinion ([N.Y. Crim. Proc. Law 1 §] 400.20[1][b]), but whether there are any 2 facts other than the predicate convictions 3 that must be found to make recidivist 4 sentencing possible (see Blakely, 542 U.S. at 5 302-303 . . .). Our answer is no. . . . 6
7 . . . . 8
9 To reiterate our analysis . . . , a 10 defendant adjudicated as a persistent felony 11 offender has a statutory right to present 12 evidence that might influence the court to 13 exercise its discretion to hand down a 14 sentence as if no recidivism finding existed, 15 while the People retain the burden to show 16 that the defendant deserves the higher 17 sentence. Nevertheless, once a defendant is 18 adjudged a persistent felony offender, a 19 recidivism sentence cannot be held erroneous 20 as a matter of law, unless the sentencing 21 court acts arbitrarily or irrationally. 22
23 The court’s opinion is, of course, 24 subject to appellate review, as is any 25 exercise of discretion. The Appellate 26 Division, in its own discretion, may conclude 27 that a persistent felony offender sentence is 28 too harsh or otherwise improvident. . . . A 29 determination of that kind, however, is based 30 not on the law but as an exercise of the 31 Appellate Division’s discretion in the 32 interest of justice as reserved uniquely to 33 that Court ([N.Y. Crim. Proc. Law §] 470.20 34 [6]). 7
35
36 7 See e.g., People v. Williams, 239 37 A.D.2d 269, 269-270, 658 N.Y.S.2d 264 (1 st
38 Dept 1997) (reducing a persistent felony 39 offender sentence in the interest of justice, 40 based on defendant’s rehabilitation) . . . . 41
42 Rivera, 833 N.E.2d at 198-99. 43
While Rivera states that two prior convictions alone render 44
a defendant “eligible for,” or “subject to,” a Class A-I sentence 45
-- or make such a sentence “possible” -- it follows the language 46
of the PFO statute in giving a sentencing court discretion to 47

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11
impose such a sentence but only if the court finds that “the 1
history and character of the defendant and the nature and 2
circumstances of [defendant’s] criminal conduct indicate that 3
extended incarceration and life-time supervision will best serve 4
the public interest . . . .” N.Y. Penal Law § 70.10; Rivera, 833 5
N.E.2d at 197-98. Rivera, therefore, confirms that, while a 6
defendant with two or more felony convictions is, by virtue of 7
that fact alone, “eligible for” and “subject to” a Class A-I 8
sentence, a sentencing court may not impose a Class A-I sentence 9
unless it has found that the history/character/criminal conduct 10
factors justify that enhanced sentence. See Rivera, 833 N.E.2d 11
at 198-99. As Rivera stated, these factors govern “whether to 12
impose the authorized persistent offender sentence” or whether 13
“to hand down a sentence as if no recidivism finding existed.” 14
Id. Further, Rivera cited as an example of the proper procedure 15
People v. Williams, 658 N.Y.S.2d 264, a decision that found a 16
Class A-I sentence to be “an improvident exercise of discretion” 17
and ordered the resentencing of the defendant “as a second felony 18
offender.” Williams, 658 N.Y.S.2d at 265; see Rivera, 833 N.E.2d 19
at 199 n.7. 20
Therefore, it is clear from the statute and from Rivera 21
that, absent findings beyond the existence of two or more felony 22
convictions, the Class A-I range may not be imposed, and a 23
defendant must be sentenced within a lesser range, usually as a 24
second felony offender. (Of course, the criminal history may in 25
some cases be sufficient to support such findings.) It is also 26

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12
clear that a Class A-I sentence usually has a statutory maximum 1
above the statutory maximum for second felony offenders. Compare 2
N.Y. Penal Law §§ 70.04(3), 70.06(3), with id. § 70.00(2)(a). 3
The New York Court of Appeals has repeatedly rejected Sixth 4
Amendment challenges to the sentencing scheme. See People v. 5
Quinones, 906 N.E.2d 1033, 1034 (N.Y. 2009); Rivera, 833 N.E.2d 6
at 195; People v. Rosen, 752 N.E.2d 844, 846 (N.Y. 2001). Before 7
Blakely and Cunningham v. California, 127 S. Ct. 856 (2007), we 8
twice held that Rosen did not unreasonably apply either Apprendi 9
v. New Jersey, 530 U.S. 466 (2000), or the Supreme Court’s later 10
decision in Ring v. Arizona, 536 U.S. 584 (2002). See Brown v. 11
Miller (“Brown II”), 451 F.3d 54, 56-57 (2d Cir. 2006) 12
(addressing both Apprendi and Ring); Brown v. Greiner (“Brown 13
I”), 409 F.3d 523, 526 (2d Cir. 2005) (addressing Apprendi). 14
But, as discussed infra, neither Brown decision addresses the 15
effect of the Supreme Court’s more recent decisions in Blakely 16
and Cunningham. 17
b) Prior State Court and Federal Proceedings Concerning the 18
Petitions 19
1) James Besser 20
Besser was convicted, following a jury trial, of one count 21
of enterprise corruption, a Class B felony, in violation of New 22
York Penal Law § 460.20. The jury found that he had committed 23
three predicate criminal acts with the intent to participate in 24
the affairs of the Colombo Organized Crime Family. 25

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New York moved to have Besser sentenced as a Class A-I 1
offender pursuant to the PFO statute. Counsel for Besser 2
registered objections to, inter alia, substantial portions of the 3
state’s statement of alleged facts regarding his history and 4
character and its supporting exhibits, which included court and 5
police records. 6
The court found the predicate felony convictions qualified 7
Besser for sentencing pursuant to the PFO statute. The judge 8
then reviewed the evidence submitted by the state that included 9
information relating to Besser’s uncharged murder attempts and to 10
a brutal beating for which charges were then pending. It 11
concluded that Besser’s “history and character warrant[ed] a 12
sentence of extended incarceration and lifetime supervision . . . 13
.” Besser received a sentence under the PFO statute of 15 years 14
to life imprisonment. Had Besser been sentenced as a second 15
felony offender, he would have been subject to a sentence of a 16
minimum of 4.5 years to a maximum of 25 years. See N.Y. Penal 17
Law § 70.06(3)-(4). 18
Besser appealed, challenging, inter alia, his sentence as 19
imposed in violation of his Sixth Amendment rights under 20
Apprendi. On May 1, 2001, the New York Court of Appeals rejected 21
that challenge, stating that because Besser had failed to raise 22
the Apprendi claim before the sentencing court, the issue was not 23
preserved. See People v. Besser, 749 N.E.2d 727, 733 (N.Y. 2001) 24
(citing Rosen, 752 N.E.2d 844). 25

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On August 26, 2002, Besser filed the present petition in the 1
Southern District. Judge Kaplan denied the petition, based on 2
our decision in Brown I, 409 F.3d 523, but “grant[ed] a 3
certificate of appealability on the question whether New York’s 4
[PFO] statute violates the rule of Apprendi . . . .” See Besser 5
v. Walsh, 2005 WL 1489141, at *1. 6
2) Vance Morris 7
Morris was convicted by a jury, of sixteen counts of first 8
degree criminal contempt, a Class E felony. See N.Y. Penal Law § 9
215.51(b). The conviction was based on two telephone threats 10
against his girlfriend in violation of four separate orders of 11
protection issued as a result of repeated violent acts and 12
general mayhem at his girlfriend’s apartment and in her 13
community. The state moved to sentence Morris as a Class A-I 14
offender under the PFO statute. Morris conceded several prior 15
felony convictions for attempted robbery, robbery, grand larceny, 16
and possession of a controlled substance, but disputed whether 17
his criminal conduct, history and character warranted an enhanced 18
sentence. At the sentencing hearing on July 24, 2002, the court 19
first determined Morris to be a PFO based on three qualifying 20
prior felony convictions. The court then examined the evidence 21
regarding Morris’s history and character. Noting the state’s 22
evidence regarding the defendant’s “relevant criminal conduct, 23
his bad acts, uncontrollable [rage], defiance of authority and 24
hostile conduct toward women,” the court sentenced Morris to 25
sixteen concurrent indeterminate terms of 15 years to life 26

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imprisonment. Had Morris been sentenced as a second felony 1
offender for any of these counts, he would have been subject to a 2
minimum of 1.5 years and a maximum of 4 years. See N.Y. Penal 3
Law § 70.06(3)-(4). 4
On appeal, Morris raised several issues, including, for the 5
first time, an Apprendi challenge to his sentence. On August 4, 6
2005, the Appellate Division unanimously affirmed, stating that 7
even if Morris had preserved the Apprendi challenge, it would be 8
rejected. See People v. Morris, 800 N.Y.S.2d 6, 7 (App. Div. 9
2005) (citing Rivera, 833 N.E.2d 194, and Rosen,752 N.E.2d 844). 10
On September 27, 2005, the New York Court of Appeals summarily 11
denied Morris leave to appeal. People v. Morris, 837 N.E.2d 744 12
(N.Y. 2005). 13
Morris subsequently petitioned for a writ of habeas corpus 14
pursuant to 28 U.S.C. § 2254. Relying on Brown I, 409 F.3d 523, 15
and Brown II, 451 F.3d 54, as well as Rivera, 833 N.E.2d 194, 16
Judge Sweet denied the petition. Morris v. Artus, 2007 WL 17
2200699, at *8-*10. Morris then brought this appeal. 18
3) William Phillips 19
Phillips was convicted by a jury of second degree robbery of 20
a candy and newspaper store, a Class C violent felony offense at 21
that time, 8 in violation of New York Penal Law § 160.10(1). The 22
state moved to have Phillips sentenced as a Class A-I offender. 23
At the sentencing hearing, Phillips did not deny his six prior 24
felony convictions, nor did he raise any constitutional challenge 25
to the PFO statute or his prior convictions. Phillips did, 26

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16
however, contest whether his criminal conduct, history, and 1
character was of the kind warranting an enhanced sentence. The 2
court found that in light of Phillips’s failure to take advantage 3
of “favorable plea bargains, minimal sentences, early parole, a 4
temporary release program, community service in lieu of 5
incarceration and a drug program,” he had shown “time and again, 6
throughout his entire adult life, that he cannot be trusted to 7
function normally in society and that he is unwilling and unable 8
to rehabilitate himself.” Phillips was sentenced to a term of 16 9
years to life in prison. If Phillips had not been sentenced 10
pursuant to the PFO statute, he would have been sentenced as a 11
second violent felony offender because of a 1987 guilty plea for 12
attempted robbery in the second degree, a Class D violent felony 13
offense at that time. See N.Y. Penal Law §§ 70.02(1), 70.04(1). 14
Had he been sentenced as a second violent felony offender, he 15
would have been subject to a determinate sentence, with a minimum 16
of 7 years and a maximum of 15 years. See N.Y. Penal Law § 17
70.04(3)(b). 18
In a collateral proceeding brought pursuant to New York 19
Criminal Procedure Law § 440.20, Phillips raised for the first 20
time an Apprendi challenge to his sentence. On June 25, 2003, 21
the court rejected his claim on the merits. 22
Thereafter, Phillips appealed both his conviction and the 23
denial of his Section 440.20 motion. On December 18, 2003, the 24
Appellate Division unanimously affirmed the underlying conviction 25
and the denial of the Section 440.20 motion, concluding that “the 26

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17
particular facts upon which the sentencing court based its 1
determination were all permissible under Apprendi . . . .” 2
People v. Phillips, 768 N.Y.S.2d 812, 812 (App. Div. 2003). The 3
New York Court of Appeals denied Phillips leave to appeal without 4
prejudice to renewal, and then, on September 30, 2004, denied 5
leave again upon reconsideration. People v. Phillips, 816 N.E.2d 6
207 (N.Y. 2004), on reconsideration, 818 N.E.2d 680 (N.Y. 2004). 7
Phillips then brought the instant petition in the Southern 8
District for a writ of habeas corpus. On June 30, 2006, Judge 9
Crotty rejected Phillips’s Apprendi challenge, relying on Brown 10
I, 409 F.3d 523, and Brown II, 451 F.3d 54. Phillips v. Artus, 11
2006 WL 1867386, at *5-*7. The court declined to issue a 12
certificate of appealability. Id. at *7. Phillips then moved 13
for a certificate of appealability in this court, which was 14
granted. 9
15
4) Carlos Portalatin 16
Portalatin was found guilty by a jury of one count each of 17
second degree kidnapping and first degree robbery in connection 18
with a carjacking incident. See N.Y. Penal Law §§ 135.20, 19
160.15. Both of these offenses are Class B violent felony 20
offenses. See N.Y. Penal Law § 70.02(1). The state moved to 21
sentence Portalatin as a Class A-I. At the sentencing hearing on 22
April 28, 2003, the trial court adjudicated Portalatin a PFO, 23
citing two prior convictions. Portalatin contended that his 24
criminal conduct, history, and character were not of the kind to 25
warrant an enhanced sentence. As to his history and character, 26

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18
the court noted that “looking back on the history of this 1
defendant, and having read these reports, it is clear that there 2
is very little in his experience or his life that would support 3
the story he gave on the witness stand . . . .” In light of 4
Portalatin’s repeated parole revocations, disinclination to 5
accept drug treatment, repeated drug charges, “inclination to 6
prey upon others,” his inability to “control his own problems,” 7
the fact that a carjacking is a “truly terrifying experience,” 8
and his displaying what appeared to be a firearm during the 9
crime, the court imposed two concurrent terms of 18 years to life 10
imprisonment. If Portalatin had not been sentenced as a PFO, he 11
would have been sentenced as a second violent felony offender due 12
to a previous conviction in 1995 for attempted burglary in the 13
second degree, a Class D violent felony offense. See N.Y. Penal 14
Law §§ 70.02(1), 70.04(1). As a second violent felony offender, 15
Portalatin would have been subject to a determinate sentence for 16
each count that was between 10 to 25 years. See N.Y. Penal Law § 17
70.04(3)(a). 18
Portalatin brought an Apprendi challenge to his sentencing 19
under the PFO statute for the first time in his appeal to the 20
Appellate Division. Finding Portalatin’s Apprendi challenge both 21
unpreserved and without merit, the court affirmed his judgment of 22
conviction and sentence on May 16, 2005. People v. Portalatin, 23
795 N.Y.S.2d 334, 335 (App. Div. 2005) (citing Rosen, 752 N.E.2d 24
844). On July 6, 2005, Portalatin’s application for leave to 25

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19
appeal was denied by the New York Court of Appeals. People v. 1
Portalatin, 5 N.Y.3d 793, 793 (2005). 2
Portalatin then sought a writ of habeas corpus in the 3
Eastern District, which Judge Gleeson granted on March 22, 2007. 4
Portalatin v. Graham, 478 F. Supp. 2d at 386. The state then 5
took this appeal. 6
5) William Washington 7
Washington was convicted by a jury of fourth degree grand 8
larceny, a Class E felony, in connection with his theft of a 9
wallet at a bus terminal. See N.Y. Penal Law § 155.30. The 10
state moved to sentence Washington pursuant to the PFO statute. 11
Washington’s memorandum in opposition raised constitutional 12
objections to the PFO statute based on Apprendi, Ring, and Harris 13
v. United States, 536 U.S. 545 (2002). At the PFO hearing on 14
January 23, 2003, Washington conceded two prior felony 15
convictions. He also reasserted his Apprendi argument and 16
contested whether his criminal conduct, history and background 17
were of the kind to warrant an enhanced sentence. At the 18
sentencing hearing on January 30, 2003, the court concluded that 19
the two unchallenged prior felony convictions triggered the PFO 20
statute. With respect to Washington’s criminal conduct, history, 21
and character, the court noted some fifty-seven arrests outside 22
of New York and fifteen theft-related misdemeanor and felony 23
convictions in New York, the defendant’s extensive pattern of 24
thefts in the same locale, and a history of recidivism placing 25
him “far beyond any rehabilitation.” The court then sentenced 26

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20
Washington to a term of 20 years to life imprisonment. Had 1
Washington been sentenced as a second felony offender, he would 2
have been subject to an indeterminate sentence of a minimum of 3
1.5 years and a maximum of 4 years. See N.Y. Penal Law § 4
70.06(3)-(4). 5
On August 4, 2005, the Appellate Division upheld the 6
constitutionality of the PFO sentencing scheme and affirmed 7
Washington’s adjudication as a persistent felony offender. See 8
People v. Washington, 799 N.Y.S.2d 217, 218 (App. Div. 2005) 9
(citing Rivera, 833 N.E.2d 194; Rosen, 752 N.E.2d 844). The 10
court nonetheless exercised its discretion to reduce the sentence 11
in the interest of justice to a Class A-I sentence of 15 years to 12
life. See id. at 217-18; see also N.Y. Penal Law § 70.00(2)-(3). 13
Thereafter, the New York Court of Appeals denied leave to appeal, 14
People v. Washington, 5 N.Y.3d 834 (2005), and on January 9, 15
2006, the United States Supreme Court denied Washington’s 16
petition for certiorari. Washington v. New York, 546 U.S. 1104 17
(2006). Washington then petitioned in the Southern District for 18
a writ of habeas corpus, which Judge Koeltl granted on August 28, 19
2007. See Washington v. Poole, 507 F. Supp. 2d 342, 344 20
(S.D.N.Y. 2007). The state then brought this appeal. 21
DISCUSSION 22
a) Standard of Review 23
We review de novo a decision to grant or deny a petition for 24
writ of habeas corpus. Morris v. Reynolds, 264 F.3d 38, 45 (2d 25
Cir. 2001). Under the Antiterrorism and Effective Death Penalty 26

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21
Act (“AEDPA”), “with respect to any claim that was adjudicated on 1
the merits in State court proceedings,” a federal court may not 2
grant habeas relief unless the state court’s resolution of the 3
claim on the merits: 4
(1) resulted in a decision 5 that was contrary to, or involved 6 an unreasonable application of, 7 clearly established Federal law, as 8 determined by the Supreme Court of 9 the United States; or 10
11 (2) resulted in a decision 12 that was based on an unreasonable 13 determination of the facts in light 14 of the evidence presented in the 15 State court proceeding. 16
17 28 U.S.C. § 2254(d). 18
A state court decision is “contrary to” clearly established 19
law for AEDPA purposes only if “the state court arrives at a 20
conclusion opposite to that reached by [the Supreme] Court on a 21
question of law or if the state court decides a case differently 22
than [the] Court has on a set of materially indistinguishable 23
facts.” Williams v. Taylor, 529 U.S. 362, 412-13 (2000) 24
(O’Connor, J., for the Court). An “unreasonable application” of 25
clearly established federal law occurs “if [a] state court 26
‘correctly identifies the governing legal rule but applies it 27
unreasonably to the facts of a particular prisoner’s case,’ or 28
refuses to extend a legal principle that the Supreme Court has 29
clearly established to a new situation in which it should 30
govern.” Hoi Man Yung v. Walker, 468 F.3d 169, 176 (2d Cir. 31
2006) (quoting Williams, 529 U.S. at 407-08) (citations omitted). 32
The proper inquiry is not whether a state court’s application of, 33

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22
or refusal to extend, the governing law was erroneous, but 1
whether it was “objectively unreasonable,” Williams, 529 U.S. at 2
409-10, “mean[ing] that petitioner must identify some increment 3
of incorrectness beyond error in order to obtain habeas relief.” 4
Cotto v. Herbert, 331 F.3d 217, 248 (2d Cir. 2003) (internal 5
quotation marks omitted). 6
Clearly established federal law “refers to the holdings, as 7
opposed to the dicta, of [Supreme Court] decisions as of the time 8
of the relevant state-court decision.” Williams, 529 U.S. at 9
412. To assess “clearly established” law, federal habeas courts 10
apply rules of retroactivity that are generally consistent with 11
those set forth in Teague v. Lane, 489 U.S. 288 (1989). See 12
Mungo v. Duncan, 393 F.3d 327, 333-34 (2d Cir. 2004). Teague 13
prohibits the retroactive application of “new” legal rules on 14
collateral review. Teague, 489 U.S. at 295-96; see also id. at 15
301 (O’Connor, J., concurring). Under Teague, “a case announces 16
a new rule if the result was not dictated by precedent existing 17
at the time the defendant’s conviction became final.” Id. at 18
301. AEDPA similarly forbids retroactive application of “new” 19
legal rules. See McKinney v. Artuz, 326 F.3d 87, 96 (2d Cir. 20
2003) (“Clearly established federal law . . . is law that is 21
‘dictated by [Supreme Court] precedent existing at the time the 22
defendant’s conviction became final.’”) (quoting Williams, 529 23
U.S. at 381 (Stevens, J., concurring)). However, as explained 24
infra, the point of reference for determining “clearly 25

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23
established law” may differ from the reference point used under 1
Teague to determine whether a legal rule is “new.” 2
AEDPA deference applies only if a state court has disposed 3
of a federal claim “on the merits” and “reduce[d] its disposition 4
to judgment.” See Sellan v. Kuhlman, 261 F.3d 303, 312 (2d Cir. 5
2001). In the present matter, petitioners’ federal claims were 6
all disposed “on the merits” by the New York courts. Phillips’s 7
federal claim was rejected “on the merits” by the state court’s 8
conclusion that “the particular facts upon which the sentencing 9
court based its determination were all permissible under Apprendi 10
. . . .” People v. Phillips, 768 N.Y.S.2d at 812. The state 11
court similarly rejected Washington’s claim “on the merits” by 12
concluding that “[t]he procedure under which defendant was 13
adjudicated a persistent felony offender is not 14
unconstitutional.” People v. Washington, 799 N.Y.S.2d at 218. 15
The federal claims raised by Portalatin, Morris, and Besser 16
were also decided “on the merits” for AEDPA purposes because each 17
state court cited People v. Rosen in ruling that those claims 18
were procedurally barred. See People v. Besser, 749 N.E.2d at 19
733; People v. Morris, 800 N.Y.S.2d at 7; People v. Portalatin, 20
795 N.Y.S.2d at 335. We held in Brown I that the state court in 21
People v. Rosen could not have invoked state procedural law and 22
barred Rosen’s Sixth Amendment claim without first having found 23
that the claim was without merit. Brown I, 409 F.3d at 532. And 24
we later held in Brown II that a citation to Rosen in holding 25
that a claim is procedurally barred establishes that the state 26

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24
court decision was interwoven with federal law. Brown II, 451 1
F.3d at 56-57. Therefore, the procedural rulings in the present 2
matter are not “adequate” and “independent” grounds for the 3
decision and do not bar us from addressing the federal claims on 4
habeas review. See Brown II, 451 F.3d at 56-57; Brown I, 409 5
F.3d at 532. We thus proceed with these appeals under AEDPA’s 6
deferential standard of review. 7
b) AEDPA Claim and “Clearly Established” Sixth Amendment Law 8
Our analysis will proceed as follows: we first address 9
whether it was objectively unreasonable to uphold petitioners’ 10
Class A-I sentences in light of the Supreme Court decisions 11
applying Apprendi. We then turn to whether that law was “clearly 12
established” at the relevant time for each petitioner. This 13
inquiry leads to two further questions: first, to what period of 14
time do we look in determining whether a legal rule was “clearly 15
established” under AEDPA; second, to what extent does AEDPA allow 16
us to consider Supreme Court cases that postdate the relevant 17
period selected. 18
1) The Apprendi Rule 19
The Sixth and Fourteenth Amendments guarantee that in 20
federal and state “criminal prosecutions, the accused shall enjoy 21
the right to a speedy and public trial, by an impartial jury 22
. . . .” U.S. Const. amend. VI; Duncan v. Louisiana, 391 U.S. 23
145, 149 (1968) (holding that the Fourteenth Amendment affords 24
defendants the right to a jury trial in state prosecutions to the 25
same extent the Sixth Amendment affords this right in federal 26

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25
prosecutions). The Supreme Court has concluded that this 1
guarantee requires that a jury, not a judge, find any facts 2
(other than the fact of a prior conviction(s)) that may increase 3
the penalty for a crime beyond the ordinary statutory maximum. 4
Apprendi v. New Jersey, 530 U.S. 466, 490 (2000). 5
In Apprendi, the petitioner was convicted of possession of a 6
firearm for an unlawful purpose, punishable under New Jersey law 7
by a term of incarceration of 5 to 10 years. Id. at 468. A 8
separate hate crime statute, however, authorized an “extended 9
term” of imprisonment of 10 to 20 years if the trial judge found 10
that “[t]he defendant in committing the crime acted with a 11
purpose to intimidate an individual or group of individuals 12
because of race, color, gender, handicap, religion, sexual 13
orientation or ethnicity.” Id. at 468-69 (quoting N.J. Stat. 14
Ann. § 2C:44-3(e)) (alteration in original). Having made such a 15
finding, the trial judge sentenced Apprendi to 12 years 16
imprisonment. Id. at 471. The Supreme Court held that the 17
enhanced sentence violated the Sixth Amendment, id. at 497, 18
concluding that other than the fact of a prior conviction, “any 19
fact that increases the penalty for a crime beyond the prescribed 20
statutory maximum must be submitted to a jury, and proved beyond 21
a reasonable doubt,” id. at 490. The Court emphasized that “the 22
relevant inquiry is one not of form, but of effect.” Id. at 494. 23
On several subsequent occasions, the Supreme Court 24
elaborated on the reach of Apprendi. In Ring, the Supreme Court 25
addressed a capital sentencing scheme that required sentencing 26

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26
judges to find at least one statutorily-enumerated aggravating 1
circumstance before imposing the death penalty. See Ring, 536 2
U.S. at 592-93. Absent such a finding and “[b]ased solely on the 3
jury’s verdict finding . . . [of guilt], the maximum punishment 4
[Ring] could have received was life imprisonment.” Id. at 597 5
(citing Ariz. Rev. Stat. § 13-703). Ring concluded that this 6
scheme ran afoul of Apprendi, id. at 609, explaining that “[i]f a 7
State makes an increase in a defendant’s authorized punishment 8
contingent on the finding of a fact, that fact -- no matter how 9
the State labels it -- must be found by a jury beyond a 10
reasonable doubt,” id. at 602. 11
Then came Blakely. Under Washington state’s Sentencing 12
Reform Act, judges were ordinarily required to impose a sentence 13
within a “standard range” that might well be significantly below 14
the statutory maximum for the underlying offense. See Blakely, 15
542 U.S. at 299. The charged offense in Blakely’s case, second 16
degree kidnapping, was a class of felony subject to a maximum 17
sentence of 10 years. Id. (citing Wash. Rev. Code §§ 18
9A.20.021(1)(b), 9A.40.030(3)). Other provisions, however, 19
further limited the range for a defendant in Blakely’s 20
circumstances to a “standard” sentencing range of 49 to 53 21
months. Id. And yet another provision permitted the sentencing 22
court to impose a sentence above that “standard” range if it made 23
factual findings on the record sufficient to support a conclusion 24
that there were “substantial and compelling reasons justifying an 25
exceptional sentence,” based on a non-exhaustive list of 26

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27
aggravating factors. Id. (quoting Wash. Rev. Code § 1
9.94A.120(2)). The sentencing judge found that, in kidnapping 2
his ex-wife, Blakely had acted with deliberate cruelty and 3
accordingly sentenced him above the standard range to a term of 4
incarceration of 90 months. Id. at 300. 5
The Supreme Court stated that review of Blakely’s sentence 6
required “apply[ing] the rule we expressed in Apprendi v. New 7
Jersey: ‘Other than the fact of a prior conviction, any fact that 8
increases the penalty for a crime beyond the prescribed statutory 9
maximum must be submitted to a jury, and proved beyond a 10
reasonable doubt.’” Blakely, 542 U.S. at 301 (quoting Apprendi, 11
530 U.S. at 490) (citation omitted). The Court then reiterated 12
that “the ‘statutory maximum’ for Apprendi purposes is the 13
maximum sentence a judge may impose solely on the basis of the 14
facts reflected in the jury verdict or admitted by the 15
defendant.” Id. at 303 (emphasis in original). Thus, for 16
purposes of Apprendi, the statutory maximum for Blakely was not 17
the 10 years prescribed for the class of felony, but the top of 18
the standard range, 53 months, the applicable maximum absent 19
additional fact-finding. See id. at 303-04. Because a judge had 20
to find facts in order to impose a sentence beyond the 53 month- 21
range, the Court concluded that Washington’s sentence violated 22
the Sixth Amendment. See id. at 313-14. 23
In so holding, Blakely rejected the argument that the 24
Apprendi rule did not apply because Washington’s sentencing laws 25
did not require the finding of any specific fact or facts, but 26

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28
rather required application of the amorphous test of “substantial 1
and compelling reasons,” id. at 299, as a prerequisite for the 2
imposition of a sentence enhanced beyond the standard range. See 3
id. at 305. The Court explained that it was irrelevant 4
“[w]hether the judge’s authority to impose an enhanced sentence 5
depends on finding a specified fact (as in Apprendi), one of 6
several specified facts (as in Ring), or any aggravating fact (as 7
[in Blakely])) . . . .” Id. It also rejected as irrelevant the 8
fact that a sentencing court, after finding aggravating facts, 9
was required to assess the appropriateness of an enhanced 10
sentence. See id. at 305 n.8 (“Whether the judicially determined 11
facts require a sentence enhancement or merely allow it, the 12
verdict alone does not authorize the sentence.” (emphasis 13
omitted)). Because the judge-made “deliberate cruelty” finding 14
resulted in Blakely being sentenced beyond 53 months, the Court 15
reversed the state court’s decision that there was no Apprendi 16
violation and remanded for further proceedings. Id. at 298, 303, 17
314. 18
Blakely clarified Apprendi by making it unambiguously clear 19
that any fact (other than a prior conviction), no matter how 20
generalized or amorphous, that increases a sentence for a 21
specific crime beyond the statutory maximum must be found by a 22
jury. Before Blakely, a court could reasonably have concluded 23
(as was argued in Blakely) that certain kinds of judicial fact- 24
finding did not violate Apprendi even if it resulted in a 25
sentence beyond a statutory maximum. Indeed, we so held in Brown 26

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29
II, 451 F.3d at 55, and Brown I, 409 F.3d at 526. Of course, 1
those decisions involved the reasonableness of New York court 2
decisions upholding the PFO statute before Blakely and do not 3
answer the question before us with regard to four of the 4
petitioners, as discussed infra. See Brown II, 451 F.3d at 59 5
n.3; Brown I, 409 F.3d at 533 & n.3. 6
In Brown I, we concluded that it was not unreasonable to 7
read Apprendi to proscribe only those sentencing schemes that 8
permit a court to find some statutorily-enumerated, specific 9
fact(s) to impose an enhanced sentence. Brown I, 409 F.3d at 10
534-35. Brown II reconsidered that holding in light of Ring and 11
concluded that Ring had not undermined Brown I. Brown II, 451 12
F.3d at 55. We held that, even after Ring, it was not 13
unreasonable “to conclude that [] determinations regarding the 14
defendant’s history, character, and offense fall into a different 15
category from the essential statutory elements of heightened 16
sentencing, or functional equivalents thereof, that were 17
addressed by the Supreme Court’s Apprendi ruling.” Id. at 58 18
(quoting Brown I, 409 F.3d at 535). In other words, because the 19
“‘amorphous’ determination” required by the statute did not 20
require “judicial factfinding of an element of the crime,” it did 21
not violate Apprendi. Id. at 59. However, while Brown I and 22
Brown II remain good law as to the issue they addressed -- 23
whether upholding the PFO statute was an unreasonable application 24
of clearly established federal law after Apprendi but before 25
Blakely/Cunningham -- Blakely makes it clear that even 26

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30
“amorphous” judicial findings that alter maximum sentences offend 1
the Sixth Amendment. 2
Cunningham v. California, 127 S. Ct. 856 (2007), also 3
requires discussion because the challenged sentencing regime, 4
California’s determinate sentencing law (“DSL”), bears a 5
remarkable similarity to both the sentencing scheme in Blakely 6
and the New York PFO statute. Under the DSL, substantive 7
offenses were assigned upper, middle, and lower range maximum 8
sentences. Id. at 861. In Cunningham’s case, the lower range 9
was 6 years, the middle range was 12 years, and the upper range 10
was 16 years. Id. at 860. Sentencing judges were required to 11
impose the middle range unless there were “circumstances in 12
aggravation or mitigation of the crime.” Id. at 861 (quoting 13
Cal. Penal Code § 1170(b)). “Circumstances in aggravation,” were 14
defined as “facts which justify the imposition of the upper 15
prison term.” Id. at 862 (quoting Cal. Jud. Council Rule 16
4.405(d)) (emphasis omitted). Such facts were to be “established 17
by a preponderance of the evidence,” and “stated orally on the 18
record.” Id. (quoting Cal. Jud. Council Rule 4.420(b), (e)). 19
The Supreme Court held in Cunningham that “[b]ecause 20
circumstances in aggravation are found by the judge, not the 21
jury, and need only be established by a preponderance of the 22
evidence, not beyond a reasonable doubt, the DSL violates 23
Apprendi’s bright-line rule.” Id. at 868 (citations omitted). 24
In reaching this conclusion, the Court rejected the contention 25
that the upper range was the relevant statutory maximum for 26

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31
Apprendi purposes and that judges were simply exercising the 1
traditional discretion common to sentencing. Id. It reiterated 2
that “[i]f the jury’s verdict alone does not authorize the 3
sentence, if, instead, the judge must find an additional fact to 4
impose the longer term, the Sixth Amendment requirement is not 5
satisfied.” Id. at 869. 6
Cunningham also rejected an attempt to compare California’s 7
mandatory sentencing scheme and the post-Booker Federal 8
Sentencing Guidelines, id. at 869-70, which had been rendered 9
advisory by the Court, see United States v. Booker, 543 U.S. 220, 10
246 (2005) (Breyer, J., for the Court). That the sentencing 11
schemes of both California and the United States required that 12
resultant sentences be reasonable did not, in the Court’s view, 13
cure the California scheme’s constitutional infirmity in 14
requiring judges to find facts to impose the increase in a 15
sentence beyond the maximum sentence prescribed by the middle 16
range. See Cunningham, 127 S. Ct. at 870. 17
2) Was Blakely “clearly established” at the relevant time 18
for each petitioner? 19
As noted, the legal rule invoked by petitioners was not 20
clearly established until Blakely clarified Apprendi. Therefore, 21
we must decide whether Blakely was clearly established federal 22
law “as of the time of the relevant state-court decision” for 23
each petitioner. Williams, 529 U.S. at 412 (O’Connor, J., for 24
the Court). If Blakely postdates the “relevant time” for any 25
petitioner, then our Brown cases would control and foreclose the 26

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32
current challenge. See Brown II, 409 F.3d at 535; Brown I, 451 1
F.3d at 59. 2
For all but one petitioner, it does not matter which formula 3
we use in assessing the “relevant time.” Besser’s conviction 4
became final well before Blakely, and our Brown decisions dispose 5
of his claim for habeas relief. Similarly, because the state 6
court decisions involving Portalatin, Morris and Washington all 7
postdate Blakely, their claims are not controlled by the Brown 8
decisions, and we must instead evaluate New York’s sentencing law 9
in light of Blakely. However, Blakely came down after the New 10
York Appellate Division decided Phillips’ appeal but before the 11
Court of Appeals of New York denied Phillips leave to appeal. 12
Phillips’ appeal thus turns on which approach we adopt in 13
determining the relevant time. 14
We have previously noted that the Supreme Court has offered 15
“inconsistent guidance” on this question. See Brown II, 451 F.3d 16
at 57 n.1; Brown I, 409 F.3d at 533 n.3. 10 However, as the Court 17
recently explained, “the relevant state-court judgment for 18
purposes of our review under AEDPA is that adjudicating the 19
merits of [petitioner’s] state habeas application, in which these 20
claims were properly raised . . . .” Abdul-Kabir v. Quarterman, 21
127 S. Ct. 1654, 1659 (2007). 22
We understand this formulation to mean that any state court 23
decision involving the merits of an Apprendi claim is an 24
application of federal law, whether or not the decision contains 25
a discussion. Even if such a decision is a denial of leave to 26

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33
appeal or denial of a motion for reconsideration, application of 1
federal law is still a factor that we must deem a state court to 2
have considered. Therefore, we understand the relevant time to 3
be the date on which a decision regarded as final under state law 4
-- which may or may not include the certiorari period (not an 5
issue here) -- has been entered in a proceeding deemed to involve 6
the merits for federal habeas purposes. We believe that rule is 7
not only fully consistent with Section 2254(d), which triggers 8
AEDPA review once a claim has been “adjudicated on the merits in 9
State court proceedings,” 28 U.S.C. § 2254(d), but also provides 10
a bright-line rule. 11
Applying this formulation here, Phillips may rely on Blakely 12
as clearly established while the state courts were actively 13
reviewing his claims. Thus, Blakely is clearly established law 14
for purposes of the petitions filed by Portalatin, Morris, 15
Washington, and Phillips. 16
3) Cunningham and “Clearly Established” Law 17
We turn to a final issue related to the term “clearly 18
established federal law.” As noted, Cunningham invalidated a 19
statutory scheme very similar to the PFO statute. The state 20
argues that we may not consider Cunningham because it postdates 21
the relevant state court decisions for the remaining petitioners. 22
We disagree. Under both AEDPA and Teague, a petitioner may rely 23
on a decision issued subsequent to the relevant period if that 24
decision is “dictated” by preexisting Supreme Court precedent. 25
See Artuz, 326 F.3d at 96; see also Williams, 529 U.S. at 381 26

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34
(Stevens, J., concurring) (quoting Teague, 489 U.S. at 301); id. 1
at 412 (O’Connor, J., for the Court). By “dictated,” we mean 2
that the result must have been “apparent to all reasonable 3
jurists” during the operative time frame. See Beard v. Banks, 4
542 U.S. 406, 413 (2004) (quoting Lambrix v. Singletary, 520 U.S. 5
518, 528 (1997)). Accordingly, neither Teague nor AEDPA preclude 6
us from considering post-dated decisions that merely restate or 7
codify “old” rules of law that were “clearly established” at the 8
time. 9
Applying that principle here, we conclude that Blakely 10
compelled the result in Cunningham and that we must therefore 11
consider it as “clearly established law” for AEDPA purposes. 12
Cunningham presented no issue of fact or law materially 13
distinguishable from Blakely because the sentencing schemes in 14
Blakely and Cunningham were “closely analogous.” See Butler v. 15
Curry, 528 F.3d 624, 635-36 (9th Cir. 2008). Both schemes 16
required a judge to impose a sentence within a standard range 17
absent a finding of circumstances (other than those taken into 18
account in the conviction) justifying an enhanced sentence. See 19
Cunningham, 127 S. Ct. at 861-62; Blakely, 542 U.S. at 304. And 20
we agree with the Ninth Circuit that Cunningham, in rejecting 21
California’s scheme, merely “reiterated the[] same points, 22
rejecting arguments already disapproved in Blakely. . . . [It] 23
did not add ‘“any new elements or criteria for”’ determining when 24
a state statute violates the Sixth Amendment.” Butler, 528 F.3d 25
at 636 (citation omitted). 26

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35
To be sure, the statutory scheme in Blakely is not precisely 1
identical to the scheme in Cunningham. But a decision does not 2
announce a “new” legal rule simply because it applies “a 3
well-established constitutional principle to govern a case which 4
is closely analogous to those which have been previously 5
considered in the prior case law.” Penry v. Lynaugh, 492 U.S. 6
302, 314 (1989) (quoting Mackey v. United States, 401 U.S. 667, 7
695 (1971) (Harlan, J., concurring in part and dissenting in 8
part)), abrogated on other grounds by Atkins v. Virginia, 536 9
U.S. 304, 307, 321 (2002). Holding otherwise would render any 10
application of Blakely a “new” rule and thus not “clearly 11
established law” for AEDPA purposes. See Butler, 528 F.3d at 12
638-39; see also Duncan v. United States, 552 F.3d 442, 445 (6th 13
Cir. 2009) (“[T]he Apprendi line of cases is long. Logically, at 14
some point in this chain . . . the rule Apprendi announced must 15
stop being a new rule in every varying application and instead 16
must become an old one that applies on collateral review.”). 17
Because Cunningham presented no issue of law or fact 18
materially distinguishable from Blakely, we conclude that Blakely 19
dictated the result in Cunningham. Indeed, the Court’s opinion 20
in Cunningham suggests as much. See Cunningham, 127 S. Ct. at 21
868 (“[T]hat should be the end of the matter . . . .” (quoting 22
Blakely, 542 U.S. at 313)). As such, we may consider it in 23
determining whether the state courts here unreasonably applied 24
clearly established federal law. 25

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36
c) AEDPA and “Contrary to,” or “Unreasonable Application” of 1
“Clearly Established Law” 2
In rejecting the Sixth Amendment challenges of Phillips, 3
Portalatin, Morris and Washington to the PFO statute, New York 4
courts relied on the views expressed by the Court of Appeals in a 5
series of opinions. We now turn to whether, in view of Blakely 6
and Cunningham, those decisions are “contrary to” or an 7
“unreasonable application of” clearly established Sixth Amendment 8
law. 9
The New York Court of Appeals has considered Apprendi 10
arguments with regard to the PFO statute on at least three 11
occasions and each time has concluded that the scheme is 12
constitutional. See Quinones, 906 N.E.2d 1033; Rivera, 833 13
N.E.2d 194; Rosen, 752 N.E.2d 844. Rivera, decided after Blakely 14
and Booker, elaborates on Rosen and offers the most thorough 15
interpretation and analysis of the PFO statute. The court’s more 16
recent decision in Quinones merely reiterates and confirms the 17
logic of Rosen and Rivera. Compare Quinones, 906 N.E.2d at 1036- 18
42, with Rivera, 833 N.E.2d at 197-201, and Rosen, 752 N.E.2d at 19
846-47. 20
In upholding the PFO statute, Rivera emphasized that the 21
history/character/criminal conduct findings are of the sort that 22
have always guided the exercise of discretion in sentencing, 23
Rivera, 833 N.E.2d at 199-200, and that “fall[] squarely within 24
the most traditional discretionary sentencing role of the judge.” 25
Id. at 200. By way of footnote, Rivera noted: 26

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37
. . . Our statutes contemplate that 1 the sentencing court–after it has 2 adjudicated the defendant a persistent 3 felony offender–will consider 4 holistically the defendant’s entire 5 circumstances and character, including 6 traits touching upon the need for 7 deterrence, retribution and 8 rehabilitation unrelated to the crime of 9 conviction. This is different from the 10 type of factfinding involved in 11 Apprendi. In this respect, we note that 12 in Brown v. Greiner, 409 F.3d 523, 534 13 [(2d Cir. 2005)], the United States 14 Court of Appeals for the Second Circuit 15 described the contested second phase of 16 our sentencing procedure as “a vague, 17 amorphous assessment” of whether the 18 public interest would be served through 19 imposition of the recidivist sentence. 20
21 Id. at 200 n.8. The Court of Appeals also analogized the 22
history/character/criminal conduct findings to the federal 23
Guidelines provision in Section 3553(a). See id. at 199. 24
Finally, it concluded, “[o]nce the defendant is adjudicated a 25
persistent felony offender, the requirement that the sentencing 26
justice reach an opinion as to the defendant’s history and 27
character is merely another way of saying that the court should 28
exercise its discretion.” Id. at 201. 29
To reiterate our earlier discussion of New York’s sentencing 30
scheme: first felony offenders are generally subject to a low 31
minimum and a maximum that varies greatly depending on the crime, 32
see N.Y. Penal Law § 70.00; second felony offenders are generally 33
subject to a higher minimum and a maximum that is the same as 34
that for first felony offenders, see N.Y. Penal Law § 70.06; a 35
defendant with two felony convictions is a PFO subject to a Class 36
A-I maximum of life but may be sentenced within a lower range, 37

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38
usually as a second felony offender or second violent felony 1
offender, if the prosecution fails to show that the 2
history/character/criminal conduct factors justify a Class A-I 3
sentence, see N.Y. Penal Law § 70.10; N.Y. Crim. Proc. Law § 4
470.20. We believe that upholding this scheme was an 5
unreasonable application of Blakely/Cunningham. There is no 6
material difference between the PFO statute and the schemes that 7
the Supreme Court found objectionable in Blakely/Cunningham. 8
Under both the Washington law at issue in Blakely and the 9
California law challenged in Cunningham, the convicted defendant 10
was “eligible for” or “subject to” a sentencing range with a high 11
maximum. 11 See Cunningham, 127 S. Ct. at 861-62; Blakely, 542 12
U.S. at 299. However, before a sentencing court could exercise 13
its discretion to impose a sentence in the range with the high 14
maximum, it had to conclude that some aggravating or compelling 15
circumstance justified it. See Cunningham, 127 S. Ct. at 861 16
(allowing for an enhanced sentence upon the finding of 17
“circumstances in aggravation”); Blakely, 542 U.S. at 299 18
(allowing for enhanced sentencing upon a finding of “substantial 19
and compelling reasons”). In the absence of such findings, these 20
sentencing courts lacked any discretion to sentence above the 21
standard range that had a lower maximum. See Cunningham, 127 S. 22
Ct. at 862; Blakely, 542 U.S. at 304. Additionally, under both 23
schemes, a decision to sentence above the standard range was 24
reviewable for evidentiary sufficiency. See Cunningham, 127 S. 25
Ct. at 861 n.2; Blakely, 542 U.S. at 299-300, 304. 26

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39
New York’s scheme is virtually indistinguishable in these 1
respects. The law allows higher-tier, Class A-I sentencing when 2
the sentencing judge has made factual findings related to a 3
defendant’s criminal history, character, and nature of the 4
criminal conduct that justify the higher sentencing range. See 5
N.Y. Penal Law § 70.10(2); N.Y. Crim. Proc. Law § 400.20(1); 6
Rivera, 833 N.E.2d at 197 n.3 (“The law goes on to require a 7
hearing or hearings, at which the People must prove to the court, 8
beyond a reasonable doubt, the fact of defendant’s prior 9
convictions, and either party may offer evidence (subject to a 10
preponderance-of-the-evidence standard) bearing on the court’s 11
exercise of discretion as to whether a recidivist sentence is 12
warranted.” (citation omitted)). To be sure, the quantity and 13
quality of the prior offenses alone may suffice to show facts 14
justifying a Class A-I sentence. See Rivera, 833 N.E.2d at 201 15
(“If, for example, a defendant had an especially long and 16
disturbing history of criminal convictions, a persistent felony 17
offender sentence might well be within the trial justice’s 18
discretion even with no further factual findings.”). Absent such 19
fact-finding, a judge lacks discretion to select the Class A-I 20
sentence and must provide a sentence authorized by the other 21
provisions of Article 70, such as a second felony offender 22
sentence. See N.Y. Penal Law § 70.10(2); N.Y. Crim. Proc. Law § 23
400.20(1); Rivera, 833 N.E.2d at 198 (“Criminal Procedure Law § 24
400.20(1) provides that a defendant may not be sentenced as a 25
persistent felony offender until the court has made the requisite 26

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40
judgment as to the defendant’s character and the criminality.”). 1
Moreover, as in Blakely, an enhanced sentence under New York law 2
is subject to a standard of appellate review focused on the 3
judge’s role as fact-finder in imposing the enhanced sentence. 4
See Blakely, 542 U.S. at 299-300; Rivera, 833 N.E.2d at 199 5
(“[O]nce a defendant is adjudged a persistent felony offender, a 6
recidivism sentence cannot be held erroneous as a matter of law, 7
unless the sentencing court acts arbitrarily or irrationally.”); 8
People v. Jennings, 822 N.Y.S.2d 501, 502 (App. Div. 2006) (“The 9
adjudication of defendant as a persistent felony offender was not 10
an abuse of discretion.”). We thus see no material difference 11
between the elements of the PFO statute and the elements of the 12
sentencing schemes found objectionable in Blakely and Cunningham. 13
For the reader’s benefit, we include a chart comparing the 14
sentences that Blakely and Cunningham were subject to, see 15
generally Cunningham, 237 S. Ct. at 861; Blakely, 542 U.S. at 16
299, with the sentences petitioner Morris was subject to under 17
the New York scheme. 18

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41
1 “Lesser”
Sentence
Requisite Judicial
Fact-Finding to
Enhance Sentence
“Enhanced” or
“Upper Tier”
Sentence
Washington 2 Sentencing 3 Law 4
5 (Blakely) 6
7
8 second-degree 9 kidnapping 10 with a 11 firearm 12
“Standard” term
of
49 to 53 months
Wash. Rev. Code
§§ 9.94A.310,
9.94A.320
“substantial and
compelling reasons
justifying an
exceptional
sentence”
Wash. Rev. Code
§ 9.94A.120(2)
10-year Maximum
Sentence
Wash. Rev. Code
§
9A.20.021(1)(b)
California 13 DSL 14
15 (Cunningham) 16
17
18
19
20
21 continuous 22 sexual abuse 23 of a child 24 under 14 25
“Middle” term
of
12 years
Cal. Penal Code
§ 288.5(a)
“the court shall
order imposition
of the middle
term, unless there
are circumstances
in aggravation or
mitigation of the
crime”
Cal. Penal Code §
1170(b)
16-year Maximum
Sentence
Cal. Penal Code
§ 288.5(a)
New York’s 26 Sentencing 27 Scheme 28
29 (Morris) 30
31
32
33
34 Class E 35 felony 36 conviction 37
38
Second Felony
Offender
Sentence –
indeterminate
term of 1.5 to
4 years
N.Y. Penal Law
§ 70.06(3)-(4)
Two qualifying
prior felony
convictions
AND
“the court . . .
is of the opinion
that the history
and character of
the defendant and
the nature and
circumstances of
his criminal
conduct indicate
that extended
incarceration and
life-time
supervision will
best serve the
public interest”
N.Y. Penal Law §
70.10
Indeterminate
term of 15 years
to life
N.Y. Penal Law
§§ 70.00(2)-(3),
70.10(2)
39

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42
In addition, the statutory labels “history and character” 1
and “nature and circumstances of [the] criminal conduct” can no 2
longer (after Blakely/Cunningham) reasonably be described as the 3
kind of judicial fact-finding constitutionally permissible, see 4
Almendarez-Torres v. United States, 523 U.S. 224, 226-27 (1998), 5
because they are amorphous and do not involve hard facts. The 6
Blakely standard determined to be a jury question was only 7
“substantial and compelling reasons,” see Blakely, 542 U.S. at 8
299, while the corresponding test in Cunningham was 9
“circumstances in aggravation,” see Cunningham, 127 S. Ct. at 10
861. If anything, the PFO statute’s history/character/criminal 11
conduct standard is less amorphous than those. Finally, 12
Cunningham rejected the attempted analogy to the federal 13
guidelines. See id. at 869-71. 14
To sum up, the PFO statute cannot be squared with the 15
statement by Justice Ginsburg in her opinion for the Court in 16
Cunningham: “If the jury’s verdict alone does not authorize the 17
sentence, if, instead, the judge must find an additional fact to 18
impose the longer term, the Sixth Amendment requirement is not 19
satisfied.” Id. at 869. 20
d) Harmless Error 21
However, it is not enough to conclude that New York state 22
courts have unreasonably applied the Sixth Amendment to Phillips, 23
Washington, Morris, and Portalatin. The state also contends that 24
any constitutional error in their sentencing was harmless. In 25
light of our conclusion that the state court decisions affirming 26

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43
Besser’s sentence were not unreasonable applications of clearly 1
established law, we need not discuss this issue with respect to 2
him. 3
Many constitutional errors are not such as to “necessarily 4
render[] a criminal trial fundamentally unfair or an unreliable 5
vehicle for determining guilt or innocence.” Washington v. 6
Recuenco, 548 U.S. 212, 218-19 (2006) (quoting Neder v. United 7
States, 527 U.S. 1, 9 (1999)). So long as the “defendant had 8
counsel and was tried by an impartial adjudicator, there is a 9
strong presumption that any other [constitutional] errors that 10
may have occurred are subject to harmless-error analysis.” Id. 11
at 218 (quoting Neder, 527 U.S. at 8) (alteration in original). 12
Accordingly, the Supreme Court has held that a state court’s 13
failure to submit a sentencing factor to the jury, a Sixth 14
Amendment violation under Blakely, is not structural error and is 15
subject to harmless error analysis. Id. at 221-22. 16
In deciding whether the application of the unconstitutional 17
statute to each petitioner was harmless, we must apply the Brecht 18
v. Abrahamson, 507 U.S. 619 (1993), test and ask if the error 19
“had substantial and injurious effect or influence” on the 20
sentence. Id. at 631 (quoting Kotteakos v. United States, 328 21
U.S. 750, 776 (1946)); see also Fry v. Pliler, 127 S. Ct. 2321, 22
2328 (2007) (holding that a federal habeas “court must assess the 23
prejudicial impact of constitutional error in a state-court 24
criminal trial under the substantial and injurious effect 25
standard . . . , whether or not the state appellate court 26

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44
recognized the error . . .”) (internal quotation marks omitted); 1
Recuenco, 548 U.S. at 221-22; Calderon v. Coleman, 525 U.S. 141, 2
145-47 (1998) (per curiam) (holding that for habeas relief to be 3
granted based on constitutional error in the capital penalty 4
phase, the error must have had substantial and injurious effect 5
on the jury’s verdict in the penalty phase); Brinson v. Walker, 6
547 F.3d 387, 395 (2d Cir. 2008); Butler, 528 F.3d at 648. 7
The State bears the burden of persuasion in such cases, Fry, 8
127 S. Ct. at 2327 n.3; United States v. Dominguez Benitez, 542 9
U.S. 74, 81 n.7 (2004), and “in cases of grave doubt as to 10
harmlessness the petitioner must win,” O’Neal v. McAninch, 513 11
U.S. 432, 437 (1995). Grave doubt exists when, “in the judge’s 12
mind, the matter is so evenly balanced that he feels himself in 13
virtual equipoise as to the harmlessness of the error.” Id. at 14
435. 15
In the present case, we believe it prudent to remand for 16
further proceedings on the question of harmlessness. No district 17
court made a detailed analysis of the harmless error issue with 18
respect to the sentences for the four petitioners, and we do not 19
believe the record on appeal is sufficiently developed for us to 20
address the matter accurately in the first instance. We 21
therefore remand the remaining four petitions for proceedings 22
consistent with this opinion. 23
CONCLUSION 24
We have considered the parties’ remaining claims and find 25
them to be without merit. For the foregoing reasons, we affirm 26

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45
the district court’s order in Besser. We vacate and remand in 1
Portalatin, Washington, Morris, and Phillips. Any subsequent 2
appeal in any of the remanded cases should be referred for 3
decision to this panel in light of the time it has invested in 4
these matters. All parties to such an appeal are directed to 5
inform the clerk of our instruction. 6
7

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46
1. We use the term “state authorities” to refer collectively to
the various state officials that have filed briefs as appellants
or appellees.
2. Because a defendant sentenced to an indeterminate sentence
receives a sentence that is a range of years, rather than a set
term, the New York statutes frequently refer to the “maximum
term” and the “minimum period of imprisonment.” See, e.g., N.Y.
Penal Law § 70.00(2)-(3). This should not be confused with this
opinion’s use of the terms “maximum” and “minimum,” which are
used to refer to the outer boundaries of the sentence, rather
than a specific range, that a defendant could permissibly
receive.
3. The PFO statute reads:
1. Definition of persistent felony
offender.
(a) A persistent felony offender is
a person, other than a persistent
violent felony offender as defined in
section 70.08, who stands convicted of a
felony after having previously been
convicted of two or more felonies, as
provided in paragraphs (b) and (c) of
this subdivision.
(b) A previous felony conviction
within the meaning of paragraph (a) of
this subdivision is a conviction of a
felony in this state, or of a crime in
any other jurisdiction, provided:
FOOTNOTES 1
2
3

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47
(i) that a sentence to a term of
imprisonment in excess of one year, or a
sentence to death, was imposed therefor;
and
(ii) that the defendant was
imprisoned under sentence for such
conviction prior to the commission of
the present felony; and
(iii) that the defendant was not
pardoned on the ground of innocence; and
(iv) that such conviction was for a
felony offense other than persistent
sexual abuse, as defined in section
130.53 of this chapter.
(c) For the purpose of determining
whether a person has two or more
previous felony convictions, two or more
convictions of crimes that were
committed prior to the time the
defendant was imprisoned under sentence
for any of such convictions shall be
deemed to be only one conviction.
2. Authorized sentence. When the
court has found, pursuant to the
provisions of the criminal procedure
law, that a person is a persistent
felony offender, and when it is of the
opinion that the history and character
of the defendant and the nature and
circumstances of his criminal conduct
indicate that extended incarceration and
life-time supervision will best serve
the public interest, the court, in lieu
of imposing the sentence of imprisonment
authorized by section 70.00, 70.02,
70.04, 70.06 or subdivision five of
section 70.80 for the crime of which
such person presently stands convicted,
may impose the sentence of imprisonment
authorized by that section for a class
A-I felony. In such event the reasons
for the court’s opinion shall be set
forth in the record.
N.Y. Penal Law § 70.10.

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48
4. Because the maximum sentence for a Class A felon is already
life imprisonment, see N.Y. Penal Law § 70.00(2)(a), neither the
second felony offender nor the PFO statute alters the maximum
sentence for such convicted defendants. Defendants convicted of
lesser felony classes (except for a terrorist offense, see N.Y.
Penal Law § 490.25(2)(c), of no pertinence here) may be subject
to a maximum sentence of life imprisonment only by virtue of the
PFO statute, see id. §§ 70.00-70.06, 70.10(2), or the persistent
violent felony offender statute, see id. § 70.08(2); see also
infra note 5.
5. There are also three increasingly harsh tiers that apply to
the sentencing for those convicted of a “violent felony offense.”
A violent felony offense is specified by statute and includes a
broad range of criminal activity. See N.Y. Penal Law § 70.02(1).
A first-time felony offender convicted of a violent felony
offense is generally sentenced to a determinate sentence based on
the class of offense. See id. § 70.02. Moreover, if there is a
finding that the violent felony offender was previously convicted
of one qualifying prior violent felony conviction, the defendant
is sentenced to a determinate sentence as a second violent felony
offender. See id. § 70.04.
If there is a finding that the violent felony offender was
previously convicted of one qualifying felony conviction, as
opposed to one qualifying violent felony conviction, the
defendant is sentenced to a determinate sentence as a second

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49
felony offender. See id. § 70.06(6). While the minimum
determinate sentence a second violent felony offender may receive
is greater than the minimum determinate sentence a second felony
offender convicted of a violent felony may receive, the maximum
determinate sentence that may be imposed is the same. Compare
id. § 70.04 with id. § 70.06(6).
Article 70 also includes a persistent violent felony
offender provision. See id. § 70.08. A persistent violent
felony offender, as opposed to a persistent felony offender, is
“a person who stands convicted of a violent felony offense . . .
or the offense of predatory sexual assault . . . or the offense
of predatory sexual assault against a child . . . , after having
previously been subjected to two or more predicate violent felony
convictions . . . .” Id. § 70.08(1)(a). This persistent
offender provision requires imposition of an indeterminate
sentence with a statutory maximum of life imprisonment solely
upon the court’s finding of qualifying predicate convictions.
Id. § 70.08(2). However, this provision is not at issue in this
appeal.
6. The pertinent provision reads:
[A Class A-I] sentence may not be
imposed unless, based upon evidence
in the record of a hearing held
pursuant to this section, the court
(a) has found that the defendant is
a persistent felony offender as
defined in subdivision one of
section 70.10 of the penal law, and
(b) is of the opinion that the
history and character of the

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50
defendant and the nature and
circumstances of his criminal
conduct are such that extended
incarceration and lifetime
supervision of the defendant are
warranted to best serve the public
interest.
N.Y. Crim. Proc. Law § 400.20(1).
7. With regard to a PFO convicted of a Class C, D, or E felony,
there is a sentencing “dead-zone” between the legally-authorized
sentencing ranges available to a court. For example, in the case
of a PFO convicted of a Class D felony, a court may impose a
sentence within a range of 15 years to life imprisonment if it
has found facts relevant to history/character/criminal conduct
that warrant such a sentence. See N.Y. Penal Law §§ 70.00(2)-
(3), 70.10(2). If the court’s fact-finding causes it to exercise
its discretion not to impose a PFO sentence, then the statutory
maximum (if not a persistent violent felony offender) generally
available to the court is 7 years. See id. §§ 70.00(2)(d),
70.02(3)(c), 70.04(3)(c), 70.06(3)(d). In such a case, a court
may not impose a sentence within a range of 8 to 14 years, as no
provision of New York law makes that a legally-authorized
sentencing range. See People v. Jennings, 822 N.Y.S.2d 501, 502
(App. Div. 2006) (“If the sentencing court had not found
defendant a persistent felony offender, the maximum sentence it
could have imposed would have been an indeterminate term of 2 to
4 years, the same sentence defendant received for each of his
prior two felonies.”); see also People v. Wilsey, 753 N.Y.S.2d

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51
232, 233 (App. Div. 2003); People v. Yale, 373 N.Y.S.2d 901, 904-
06 (App. Div. 1975). With regard to Class B felons, a different
kind of dead-zone exists. These felons may be sentenced within
the Class A-I range, but with maximum sentences of 25, see N.Y.
Penal Law §§ 70.00(2)(b), 70.02(3)(a), 70.04(3)(a), 70.06(3)(b),
70.06(6)(a), or 30 years, see id. § 70.02(3)(a). The dead zone
here is between the maximum term of years and life imprisonment.
Such PFOs may be sentenced to life imprisonment if the requisite
fact-findings as to history/character/criminal conduct are made.
See id. § 70.10(2); N.Y. Crim. Proc. Law § 400.20(1).
8. New York’s Penal Law has since been amended, and now
violations of New York Penal Law § 160.10(1) are Class C felony
offenses.
9. We certified three issues: (i) which date -– that of the
entry of the Appellate Division’s opinion, the date the New York
Court of Appeals denied leave to appeal, or the date upon which
the conviction became final -– is the relevant time for
determining the applicable Supreme Court precedent; (ii) if
Blakely v. Washington, 542 U.S. 296 (2004), applies, whether the
state court’s determination was an unreasonable application of
the holding in that case; and (iii) what is the effect, if any,
of People v. Rivera, 833 N.E.2d 194 (N.Y. 2005).
10. The confusion originates with Williams v. Taylor, 529 U.S.

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52
362 (2000), which considered the interplay between AEDPA and
Teague v. Lane, 489 U.S. 288 (1988). See Williams, 529 U.S. at
412 (O’Connor, J., for the Court). As we noted earlier, the
Court read the term “clearly established federal law” as
generally codifying Teague v. Lane’s rule against retroactive
application of cases announcing “new” legal rules. See id. at
390-91 (Stevens, J., for the Court) (citing Teague, 489 U.S. at
301). However, the court gave two different answers as to
whether the operative period for assessing “clearly established”
law was the same as the period for determining whether a rule is
“new” for Teague purposes. Under Teague, the relevant period is
“the time the defendant’s conviction became final.” See Teague,
489 U.S. at 301 (O’Connor, J., concurring). Justice Stevens,
speaking for the Court, concluded that the relevant period for
AEDPA purposes was the same. See Williams, 529 U.S. at 390
(Stevens, J., for the Court). Justice O’Connor, speaking later
for the Court, concluded that habeas courts should look to
“clearly established” law at the time of the “relevant state-
court decision” or “state-court adjudication.” Id. at 412
(O’Connor, J., for the Court).
11. Indeed, the statute in Blakely stated that the maximum
sentence for the crime was the higher limit but was held
unconstitutional because a “standard” sentencing range with a
lower limit was mandatory absent the required findings. See
Blakely, 542 U.S. at 299, 303-05.

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