The Honorable Richard Mills, of the United States District Court for the Central… v. Rosa UNITED STATES COURT OF APPEALS 1 FOR THE SECOND CIRCUIT 2 August Term, 2006 3 4…

* The Honorable Richard Mills, of the United States
District Court for the Central District of Illinois, sitting by
designation.
05-3621-cr
United States v. Rosa
UNITED STATES COURT OF APPEALS 1
FOR THE SECOND CIRCUIT 2
August Term, 2006 3
4
(Argued: April 27, 2007 Final Submissions: May 4, 2007 5
Decided: October 30, 2007 Errata Filed: November 19, 2007) 6
Docket No. 05-3621-cr 7
8
------------------------------------- 9
UNITED STATES OF AMERICA, 10
Appellee, 11
- v - 12
EDUARDO ROSA, 13
Defendant-Appellant. 14
------------------------------------- 15
Before: KEARSE and SACK, Circuit Judges, and MILLS, District 16
Judge.*
17
18
The defendant appeals from that portion of a judgment 19
of conviction in the United States District Court for the 20
Southern District of New York (Charles L. Brieant, Judge) that 21
sentenced him to the statutory mandatory minimum of 180 months' 22
imprisonment based on the court's finding that he is a violent 23
felon under the Armed Career Criminal Act, 18 U.S.C. § 924(e). 24
We conclude that no evidence before the district court 25
established that a "guilty plea [resulting in a predicate state 26

-- 1 of 40 --

2
conviction] necessarily admitted, and supported a 1
conviction for," Shepard v. United States, 544 U.S. 13, 16 2
(2005), a crime or "act of juvenile delinquency involving the use 3
or carrying of a firearm . . . that would be punishable by 4
imprisonment for [a] term [exceeding one year]," 18 U.S.C. 5
§ 924(e)(2)(B). 6
Vacated and remanded for resentencing. 7
JESSE M. FURMAN, Assistant United States 8
Attorney for the Southern District of 9
New York (Michael J. Garcia, United 10
States Attorney, Jonathan S. Kolodner, 11
Assistant United States Attorney, on the 12
brief), New York, New York, for 13
Appellee. 14
PAUL P. RINALDO, Forest Hills, New York, 15
for Appellant. 16
SACK, Circuit Judge: 17
This appeal presents the narrow question of whether, 18
under the circumstances here presented, Eduardo Rosa's 1991 New 19
York state-court guilty plea to a charge of Robbery in the First 20
Degree qualifies as a "violent felony" conviction under the Armed 21
Career Criminal Act, 18 U.S.C. § 924(e) (the "ACCA"). The 22
district court decided that it did, and that, therefore, it was 23
bound to impose on Rosa a mandatory minimum sentence of fifteen 24
years' (180 months') imprisonment under the ACCA. 25
We disagree. Under Shepard v. United States, 544 U.S. 26
13 (2005), decided shortly before the district court handed down 27
this sentence, the district court was required to determine 28
whether Rosa's "earlier guilty plea necessarily admitted, and 29

-- 2 of 40 --

1 The word "gun" has been used frequently during the course
of these proceedings. The statutory word with which we are
concerned, however, is "firearm." See, e.g., 18 U.S.C.
§ 924(e)(2)(B). It is important for purposes of addressing this
appeal that not all guns are firearms -- BB guns and staple guns,
for example, are not. See, e.g., United States v. Jones, 222
F.3d 349, 352 (7th Cir. 2000) (jury had "a sufficient basis to
reasonably conclude that Mr. Jones knew that he possessed a
3
supported a conviction for," id. at 16, "an[] act of juvenile 1
delinquency involving the use or carrying of a firearm . . . that 2
would be punishable by imprisonment for [a] term [exceeding one 3
year] if committed by an adult," 18 U.S.C. § 924(e)(2)(B). In 4
doing so, the court was "limited to the terms of the charging 5
document, the terms of a plea agreement or transcript of colloquy 6
between judge and defendant in which the factual basis for the 7
plea was confirmed by the defendant, or to some comparable 8
judicial record of this information." Shepard, 544 U.S. at 26. 9
No such document, at least none submitted to the district court, 10
established that Rosa's 1991 "guilty plea necessarily admitted, 11
and supported a conviction for," id. at 16, "an[] act of juvenile 12
delinquency involving the use or carrying of a firearm . . . that 13
would be punishable by imprisonment for [a] term [exceeding one 14
year] if committed by an adult," 18 U.S.C. § 924(e)(2)(B). We 15
therefore vacate the sentence and remand for resentencing. 16
BACKGROUND 17
On January 28, 2004, New York State police officers, 18
acting on a tip from a confidential informant, executed a search 19
warrant for the basement of Eduardo Rosa's home. There, they 20
discovered two .45 caliber handguns,1 142 rounds of ammunition, 21

-- 3 of 40 --

'firearm' [in violation of § 922(g)(1)] and not a BB gun").
4
and a bullet-proof vest. Rosa was arrested on the same day. He 1
was indicted on February 24, 2004. He was charged with two 2
counts of being a felon in possession of a firearm in violation 3
of 18 U.S.C. § 922(g)(1) (Counts One and Two), and one count of 4
possession of body armor after having been convicted of a felony 5
that is a crime of violence in violation of 18 U.S.C. § 931 6
(Count Three). 7
A superseding indictment (the "Superseding Indictment") 8
was returned on January 18, 2005, less than one week before trial 9
was scheduled to begin in the United States District Court for 10
the Southern District of New York (Charles L. Brieant, Judge). 11
It contained the same three charges as the original indictment 12
but added allegations in Counts One and Two that Rosa had "three 13
[prior] convictions for either violent felony or serious drug 14
offenses, as those terms are defined in [the ACCA, 18 U.S.C. 15
§ 924(e)(2)]." Superseding Indictment, United States v. Rosa, 16
No. S1 04-cr-176 (CLB) (S.D.N.Y. Jan. 19, 2005), at 1-3. 17
On the morning of January 24, 2005, the day on which 18
the trial was scheduled to begin, Rosa pleaded guilty, without a 19
formal plea agreement, to all three counts of the Superseding 20
Indictment. 21
According to the Presentence Investigation Report 22
("Federal PSR"), Rosa previously had been convicted of eight 23
other offenses. The Probation Office and the government 24

-- 4 of 40 --

5
classified three of his prior convictions as "violent felonies" 1
within the meaning of the ACCA: 2
1) On May 23, 1991, Rosa was convicted in New York, 3
after a guilty plea, of Robbery in the First Degree, a Class B 4
felony, in Westchester County Court. He received an adjudication 5
as a Youthful Offender and was sentenced to probation. 6
2) On October 15, 1993, Rosa was convicted in a North 7
Carolina state court of the felony of assault with a deadly 8
weapon with intent to kill or inflicting serious injury. 9
3) On October 14, 1997, Rosa was convicted of Assault 10
in the Second Degree, a Class D felony, in Westchester County 11
Court. 12
Rosa concedes that the second and third convictions 13
qualify as violent felonies for ACCA purposes. He denies, 14
however, that the first conviction, for Robbery in the First 15
Degree, also qualifies as a "violent felony" under the ACCA. If 16
it did, Rosa would be subject to a mandatory minimum sentence of 17
fifteen years' imprisonment. 18 U.S.C. § 924(e)(1). The narrow 18
question of whether it was properly so classified is the focus of 19
this appeal. 20
1991 Robbery Conviction 21
On November 19, 1990, at age fifteen, Rosa and one or 22
more of his acquaintances robbed another person of his jacket. 23
On March 13, 1991, in an indictment in Westchester 24
County Supreme Court, Rosa, along with co-defendant Steven 25
Warren, was charged on four counts. The "First Count" accused 26

-- 5 of 40 --

2 Under New York law, a
"[b]ill of particulars" is a written statement by the
prosecutor specifying . . . items of factual
information which are not recited in the indictment and
which pertain to the offense charged and including the
substance of each defendant's conduct encompassed by
the charge which the people intend to prove at trial on
their direct case . . . .
N.Y. C.P.L. § 200.95(1)(a).
6
Rosa and Warren of Robbery in the First Degree pursuant to New 1
York Penal Law § 160.15(4): 2
The defendants, in the County of Westchester 3
and State of New York, on or about November 4
19, 1990, each aiding and abetting the other 5
and acting in concert, did forcibly steal 6
property from another person, and in the 7
course of the commission of the crime and in 8
immediate flight therefrom, displayed what 9
appeared to be a pistol, revolver and other 10
firearm, to wit, a handgun. This is an Armed 11
Felony offense. 12
Indictment of Steven Warren and Edwardo [sic] Rosa, Supreme 13
Court, Westchester Cty., Nos. 91-0239-01, -02, filed Mar. 13, 14
1991 (the "1991 Indictment"), at 1. 15
On March 26, 1991, some two weeks later, the state 16
prosecutor filed a Bill of Particulars.2 In a list of evidence 17
subject to discovery and inspection, the Bill of Particulars 18
referred to a "small .22 cal. type gun" that was not recovered 19
and therefore would not be submitted as physical evidence at 20
trial as a "[w]eapon[] used in the crime." People v. Rosa, 21
Indictment No. 91-239-02, Consent Order dated Mar. 28, 1991 22
("Bill of Particulars"), at 5. The Bill of Particulars set forth 23
the "substance of the defendant's conduct encompassed by the 24

-- 6 of 40 --

7
charges set forth in the indictment which the People intend to 1
prove upon . . . trial," id. at 1: "The group did place a gun in 2
the stomach area of the victim while stealing his jacket," id. 3
(unpaginated attachment). 4
Rosa pleaded guilty to Robbery in the First Degree. 5
The other three charges were apparently thereafter discontinued. 6
During the plea colloquy, Rosa admitted that he aided and abetted 7
other people who forcibly stole property from another while 8
"display[ing] what appeared to be a pistol, revolver or other 9
firearm, to wit, a handgun." But Rosa denied that he ever 10
carried a handgun. Although his counsel referred to a "pistol" 11
during the colloquy, throughout the plea allocution the judge 12
consistently adhered to the terminology of the charge -- that 13
someone other than Rosa displayed what appeared to be a handgun. 14
In accepting the plea, the judge and the defendant 15
engaged in the following colloquy: 16
[Judge] Q Mr. Rosa, do you admit to the crime 17
of robbery in the first degree? 18
[Rosa] A Yes. 19
. . . 20
Q Do you admit at that time and 21
place, while aiding and abetting 22
and acting in concert with [other] 23
individuals, you did forcibly steal 24
property from another person, that 25
person being Mr. Romeo? 26
A Yes. 27
Q. And do you admit that while aiding 28
and abetting and acting in concert 29
with those other individuals, you 30

-- 7 of 40 --

8
did engage in a fight with Mr. 1
Romeo and you did display what 2
appeared to be a pistol, revolver 3
or other firearm, to wit, a 4
handgun? 5
A Not me. 6
Q Did someone else that you were 7
aiding and abetting and acting in 8
concert with, that is the question? 9
A Yes. 10
Q So while you yourself may not have 11
possessed what appeared to be a 12
handgun, did you, was one displayed 13
by the people with whom you were 14
acting in concert and aiding and 15
abetting? 16
A Yes. 17
Q And that was in the course of 18
commission of the robbery and the 19
stealing of the property from Mr. 20
Romeo? 21
A Yes. 22
People v. Rosa, Indictment No. 0239-91, Westchester County Ct., 23
Tr. of Plea, Apr. 19, 1991 ("1991 Plea Tr."), at 15-17. 24
The state presentence report relating to Rosa's 1991 25
conviction ("State PSR") included several references to a black 26
handgun. It cited a statement by the victim that "he felt and 27
observed a black handgun pressed into his stomach." It also 28
noted that a bus driver said he saw one of the perpetrators 29
"holding what appeared to be a black automatic handgun." But the 30
State PSR also described Rosa as saying that a co-defendant 31
"apparently had in his possession a BB gun." 32

-- 8 of 40 --

9
The state trial judge made no direct findings 1
pertaining to the State PSR or the actual use of a firearm. The 2
judge's only mention of a gun -- rather than "what appeared to 3
be" a gun -- was made during the sentencing hearing to 4
acknowledge that one of the circumstances supporting a more 5
lenient sentence was that Rosa "was not the one who wielded the 6
gun." People v. Rosa, Indictment No. 0239-91, Westchester County 7
Ct., Tr. of Sentencing, May 23, 1991, ("1991 Sentencing") at 9. 8
Rosa's attorney, seeking to minimize the sentence, also referred 9
to a gun at that hearing: "[I]t was not Eduardo [Rosa] who had 10
the gun in this particular incident." Id. at 5. As noted, he 11
also referred to a "pistol" during the plea allocution in 12
explaining what Rosa was not pleading to. See 1991 Plea Tr. at 13
15 ("Your Honor, Mr. Rosa can't admit to displaying a 14
pistol. . . . He can admit to aiding and abetting of displaying 15
a pistol but not that he did it himself.") 16
District Court Sentencing 17
The Federal PSR provided no explanation for its 18
characterization of the 1991 robbery conviction as a conviction 19
of a violent felony. In describing this prior conviction, it 20
referenced the State PSR, including the passage where the victim 21
of the robbery stated that he felt a black handgun pressed 22
against him. The Probation Office's sentencing recommendation 23
corresponded to what the government had set forth in a Pimentel 24
letter dated January 23, 2005. See United States v. Pimentel, 25
932 F.2d 1029 (2d Cir. 1991). Rosa made no objection to the 26

-- 9 of 40 --

10
Probation Office regarding the Federal PSR. He did, however, 1
submit a letter to the district court on May 11, 2005, objecting 2
to the PSR's assertion that Rosa qualified as an armed career 3
criminal under the ACCA. 4
At sentencing in the district court, the government 5
acknowledged "that unless [the putative weapon] was in fact a 6
real gun, [the robbery conviction] wouldn't count" as a "violent 7
felony" under the ACCA. United States v. Rosa, No. 04-cr-176 8
(CLB) (S.D.N.Y. June 21, 2005), Sentencing Tr. ("Sentencing Tr.") 9
at 12; see 18 U.S.C. § 924(e)(2)(B) (defining "violent felony"). 10
But the government maintained that the object used must be 11
inferred to have been a firearm, and, therefore, that Rosa 12
qualified as an Armed Career Criminal under the statute. United 13
States v. Rosa, No. 04-cr-176 (CLB), Letter from Government to 14
the District Court dated June 3, 2005 ("Sentencing Mem."), at 8- 15
9. 16
In its Sentencing Memorandum, the government asserted 17
that Rosa's 1991 conviction satisfied the statutory requirements 18
for three reasons: 19
First, the government argued, the defendant admitted 20
that a firearm was used by pleading guilty to Robbery in the 21
First Degree, thereby waiving an affirmative defense that the 22
firearm "was not a loaded weapon from which a shot . . . could be 23
discharged." N.Y. Penal Law § 160.15(4). Because the 24
availability of this affirmative defense is the only relevant 25
distinction here between first and second degree robbery, the 26

-- 10 of 40 --

3 The district court also denied an additional one-point
reduction for acceptance of responsibility. The defendant does
not appeal this determination.
11
government asserted, the defendant's plea to first degree robbery 1
waived the affirmative defense and logically required the 2
conclusion that the offense involved a gun. Sentencing Mem. at 3
8-9. 4
Second, the government asserted, the records from the 5
state court proceeding, including the State PSR, the Bill of 6
Particulars, and the sentencing transcript, establish that the 7
perpetrator wielded a firearm. Because Rosa need not be the one 8
who carried the gun as long as the crime "involv[ed]" its use, 9
United States v. King, 325 F.3d 110 (2d Cir. 2003), the offense 10
qualified as a "violent felony." Sentencing Mem. at 7. 11
Finally, the government argued, by failing to object to 12
the Federal PSR, which included language from the State PSR in 13
which the victim referred to a gun, Rosa waived any objection to 14
this characterization of the state offense. Id. at 11. 15
The district court accepted the government's arguments, 16
concluding that Rosa was a "career criminal under the [United 17
States Sentencing Guidelines ("U.S.S.G." or the "Guidelines")]." 18
Sentencing Tr. at 25. After applying the Guidelines enhancement 19
for an armed career criminal pursuant to U.S.S.G. § 4B1.4, and a 20
two-level reduction for acceptance of responsibility,3 the 21
defendant's net offense level was 31. With a criminal history 22
category of VI, his Guidelines sentencing range was 188 to 235 23

-- 11 of 40 --

4 Without the sentencing enhancement as a career criminal
under U.S.S.G. § 4B1.4(b)(3)(B), defense counsel asserted that
the Guidelines range would have been 84 to 105 months based on a
net offense level of 22 and criminal history category VI.
5 Section 924(e) provides:
(1) In the case of a person who violates section
922(g) of this title and has three previous
convictions by any court referred to in section
922(g)(1) of this title for a violent felony or a
serious drug offense, or both, committed on
occasions different from one another, such person
shall be fined under this title and imprisoned not
less than fifteen years, and, notwithstanding any
other provision of law, the court shall not
suspend the sentence of, or grant a probationary
sentence to, such person with respect to the
conviction under section 922(g).
(2) As used in this subsection--
. . .
(B) the term "violent felony" means any crime
punishable by imprisonment for a term exceeding
one year, or any act of juvenile delinquency
involving the use or carrying of a firearm,
knife, or destructive device that would be
punishable by imprisonment for such term if
12
months.4 The court then imposed a sentence of the mandatory 1
minimum -- 180 months -- for Counts One and Two, and 36 months' 2
imprisonment for Count Three, all to be served concurrently. 3
Rosa appeals his sentence. 4
DISCUSSION 5
I. Issue Presented 6
The Armed Career Criminal Act, 18 U.S.C. § 924(e), 7
"mandates a minimum 15-year prison sentence for anyone possessing 8
a firearm after three prior convictions for serious drug offenses 9
or violent felonies." Shepard v. United States, 544 U.S. 13, 15 10
(2005).5 As relevant here, the term "violent felony" includes 11

-- 12 of 40 --

committed by an adult, that--
(i) has as an element the use, attempted use,
or threatened use of physical force against
the person of another; or
(ii) is burglary, arson, or extortion,
involves use of explosives, or otherwise
involves conduct that presents a serious
potential risk of physical injury to another;
and
(C) the term "conviction" includes a finding
that a person has committed an act of juvenile
delinquency involving a violent felony.
18 U.S.C. § 924(e).
6 Rosa does not contest that his first conviction satisfies
the requirements of subsection (i) or (ii) of 18 U.S.C.
§ 924(e)(2)(B).
13
"any act of juvenile delinquency [1] involving the use or 1
carrying of a firearm, knife, or destructive device that [2] 2
would be punishable by imprisonment for [a term exceeding one 3
year] if committed by an adult." 18 U.S.C. § 924(e)(2)(B).6
4
Rosa does not dispute that his 1991 conviction for First Degree 5
Robbery, a Class B Felony, would have been punishable in New York 6
by a term of imprisonment of more than one year. See N.Y. Penal 7
Law § 160.15 ("Robbery in the first degree is a class B 8
felony."); id. § 70.00(2)(b) (maximum sentence for a Class B 9
felony is twenty-five years). 10
New York law defines First Degree Robbery, in pertinent 11
part, as follows: 12
A person is guilty of robbery in the first 13
degree when he forcibly steals property and 14
when, in the course of the commission of the 15
crime or of immediate flight therefrom, he or 16
another participant in the crime: 17
. . . 18

-- 13 of 40 --

14
4. Displays what appears to be a pistol, 1
revolver, rifle, shotgun, machine gun or 2
other firearm; except that in any 3
prosecution under this subdivision, it 4
is an affirmative defense that such 5
pistol, revolver, rifle, shotgun, 6
machine gun or other firearm was not a 7
loaded weapon from which a shot, readily 8
capable of producing death or other 9
serious physical injury, could be 10
discharged. Nothing contained in this 11
subdivision shall constitute a defense 12
to a prosecution for, or preclude a 13
conviction of, robbery in the second 14
degree, robbery in the third degree or 15
any other crime. 16
Id. § 160.15(4) (emphasis added); see also People v. Padua, 297 17
A.D.2d 536, 539, 747 N.Y.S.2d 205, 208 (1st Dep't 2002) 18
(describing the state's burden when charging a defendant under 19
section 160.15(4)). Count One of the 1991 Indictment against 20
Rosa and his codefendant tracked the statute. See 1991 21
Indictment at 1. 22
During his plea colloquy in state court, as to Count 23
One, the only count to which he pleaded, Rosa admitted that he 24
had aided and abetted another in "forcibly steal[ing] property 25
from another person" and that "what appeared to be a 26
handgun . . . was . . . displayed by the people with whom [he 27
was] acting in concert and aiding and abetting." 1991 Plea Tr. 28
at 16. These admissions regarding "what appeared to be a 29
handgun" satisfied the elements of the First Degree Robbery crime 30
with which he was charged. See N.Y. Penal Law § 160.15(4). But, 31
standing alone, they do not satisfy the elements of a "violent 32
felony" as defined by the ACCA. To be a violent felony, the 33

-- 14 of 40 --

15
crime of conviction must "involv[e] the use or carrying of a 1
firearm." 18 U.S.C. § 924(e)(2)(B) (emphasis added). Because, 2
as the government concedes, the 1991 conviction is a "violent 3
felony" only if the crime involved a firearm, Sentencing Tr. at 4
12, the district court was confronted with the question of 5
whether the 1991 crime involved a firearm. Adopting the 6
government's arguments, the district court determined that it 7
did. 8
The sole question for us on appeal is: Did the 9
district court properly determine that Rosa's 1991 state-court 10
conviction "involv[ed] the use or carrying of a firearm," as 11
opposed to the use of a BB gun, or something else other than a 12
firearm, thereby making it a "violent felony" for ACCA purposes? 13
To answer this question we must consider whether the district 14
court looked to appropriate sources in determining the nature of 15
Rosa's 1991 conviction for ACCA purposes. See Shepard, 544 U.S. 16
at 16 (addressing "whether a sentencing court can look to police 17
reports or complaint applications to determine whether an earlier 18
guilty plea necessarily admitted, and supported a conviction for, 19
generic burglary," which is a "violent felony" under the ACCA). 20
Rosa argues that the district court erred in applying 21
the fifteen-year mandatory minimum under the ACCA because the 22
state court record does not necessarily demonstrate that the 1991 23
conviction for robbery involved a firearm, and, therefore, the 24
government did not prove the robbery conviction was for a 25

-- 15 of 40 --

7 Rosa also argues that, even if a firearm were used in the
offense, Rosa did not carry it and the ACCA does not apply to a
crime where a confederate, and not the defendant, carried a gun.
We have previously rejected a very similar argument. See United
States v. King, 325 F.3d 110, 113 (2d Cir. 2003) ("The word
'involving' has expansive connotations, and we think it must be
construed as extending the focus of § 924(e) beyond the precise
offenses of distributing, manufacturing, or possessing, and as
encompassing as well offenses that are related to or connected
with such conduct.").
8 The government contends that we should review the
district court's decision for clear error, following United
States v. Houman, 234 F.3d 825 (2d Cir. 2000) (per curiam). In
Houman, "print-outs of [the defendant's] criminal history . . .
list[ed] [his previous] conviction as one for theft," but
contemporaneous court records listed the conviction as one for
robbery. Id. at 827. We applied clear error review and upheld
the district court's decision to "credit[] the contemporaneous
court records over the later criminal history tabulations." Id.
As we explained, "[t]he court used this information [in the
indictment] solely for the purpose of determining whether it was
more likely that Houman was convicted of robbery than of theft,
not for the purpose of looking beyond the elements of a theft
16
"violent felony" under the ACCA.7 The government's arguments are 1
essentially the same as those rehearsed above that it made to, 2
and were accepted by, the district court. 3
II. Standard of Review 4
"[T]he government bears the burden of establishing (by 5
a preponderance of the evidence), the existence of prior violent 6
felony convictions when seeking a sentence enhancement pursuant 7
to U.S.C. § 924(e)." United States v. Brown, 52 F.3d 415, 425 8
(2d Cir. 1995). The questions of what documents a district court 9
may rely on to determine the nature of a prior conviction and of 10
the scope of a district court's authority to make factual 11
findings are questions of law, Shepard, 544 U.S. at 16; id. at 24 12
(opinion of Souter, J.), which we review de novo.8
13

-- 16 of 40 --

conviction to find that the underlying conduct was violent in
nature." Id. (emphasis added). The court here, in contrast,
sought to determine the nature of the conduct underlying the
previous conviction. The questions presented here, similar to
those presented in Shepard, concern the district court's
authority to make a factual finding about the nature of the
conviction, and are thus questions of law that require de novo
review.
9 The Supreme Court most recently discussed the ACCA in
James v. United States, ___ U.S. ___, 127 S. Ct. 1586 (2007).
There, the Court held that, under Florida law, attempted burglary
is considered a "violent felony" under the ACCA because it
"'involv[es] conduct that presents a serious potential risk of
physical injury to another.'" Id. at 1591 (quoting 18 U.S.C.
§ 924(e)(2)(B)(ii)).
17
III. Determining the Character of a Prior Guilty Plea 1
In Taylor v. United States, 495 U.S. 575 (1990), the 2
Court endorsed a "categorical approach" to determining whether a 3
prior conviction qualifies as a "violent felony" under the ACCA. 4
The sentencing court generally must "look only to the fact of 5
conviction and the statutory definition of the prior offense." 6
Id. at 602. Where, as in Taylor (and here), the statutory 7
definition of the state crime of conviction encompasses both 8
crimes that would qualify as a "violent felony" and crimes that 9
would not, however, the Taylor Court concluded that a broader 10
inquiry is permissible. Id. If, as in Taylor (but not here), 11
guilt of the prior offense was determined at trial, that broader 12
inquiry may include the charging document and jury instructions, 13
which define the offense of conviction. Id.9
14
Shepard and Taylor both addressed the question whether 15
a burglary conviction in a state whose law defined "burglary" 16
more broadly than the "generic" definition of burglary -- for 17

-- 17 of 40 --

10 A conviction for (generic) burglary is a conviction for
a "violent felony" under the ACCA. 18 U.S.C. § 924(e)(B)(ii);
see also Taylor, 495 U.S. at 577-78 ("[The ACCA also] provides a
sentence enhancement for a defendant who is convicted under 18
U.S.C. § 922(g) (unlawful possession of a firearm) and who has
three prior convictions for specified types of offenses,
including 'burglary.'").
18
example, a state that defined burglary as including breaking and 1
entry into a building or a boat, in contrast to "generic" 2
burglary, which is limited to breaking and entry into buildings 3
-- was based on facts that could support a conviction for 4
"generic" burglary, and thus could fit the definition of "violent 5
felony" under the ACCA.10 Shepard addressed a question left open 6
by Taylor: What may a district court consider to determine 7
whether the offense of conviction following a guilty plea, rather 8
than trial, qualifies as a "violent felony"? Shepard, 544 U.S. 9
at 16. 10
In Shepard, the district court had not applied the 11
ACCA's fifteen-year mandatory minimum sentence because it had 12
declined to look to "police reports or complaint applications to 13
determine whether an earlier guilty plea necessarily admitted, 14
and supported a conviction for, generic burglary." Id. Without 15
this evidence, "the District Court found that the Government had 16
failed to carry its burden to demonstrate that Shepard had 17
pleaded to three generic burglaries." Id. at 18-19. The First 18
Circuit vacated the sentence and remanded for resentencing 19
"[a]fter observing that Shepard had never 'seriously disputed' 20
that he did in fact" commit the acts described in the police 21

-- 18 of 40 --

19
reports and complaint applications. Id. at 19 (citation 1
omitted). 2
The Supreme Court reversed. It concluded that "enquiry 3
under the ACCA to determine whether a plea of guilty to burglary 4
defined by a nongeneric statute necessarily admitted elements of 5
the generic offense is limited to the terms of the charging 6
document, the terms of a plea agreement or transcript of colloquy 7
between judge and defendant in which the factual basis for the 8
plea was confirmed by the defendant, or to some comparable 9
judicial record of this information." Id. at 26. 10
Like jury instructions in a jury case, or "the details 11
of a generically limited charging document . . . in any sort of 12
case," documents stating the facts to which the defendant 13
admitted in entering the plea will generally inform a later court 14
on the crucial question: "whether the plea had 'necessarily' 15
rested on the fact identifying the burglary as generic." Id. at 16
21. The Court rejected the government's argument "for a wider 17
evidentiary cast, . . . going beyond conclusive records made or 18
used in adjudicating guilt and looking to documents submitted to 19
lower courts even prior to charges," id., because such an 20
approach would "ease away from the Taylor conclusion, that 21
respect for congressional intent and avoidance of collateral 22
trials require that evidence of generic conviction be confined to 23
records of the convicting court approaching the certainty of the 24
record of conviction in a generic crime State," id. at 23. 25

-- 19 of 40 --

20
A plurality of the Court was of the view that 1
developments since Taylor -- particularly Jones v. United States, 2
526 U.S. 227 (1999), and Apprendi v. New Jersey, 530 U.S. 466 3
(2000) -- further justify "adher[ing] to the demanding 4
requirement that any sentence under the ACCA rest on a showing 5
that a prior conviction 'necessarily' involved (and a prior plea 6
necessarily admitted) facts equating to generic burglary." 7
Shepard, 544 U.S. at 24 (opinion of Souter, J.) (emphasis added). 8
Jones and Apprendi established the rule that "for the sake of 9
preserving the Sixth Amendment right, . . . any fact other than a 10
prior conviction sufficient to raise the limit of the possible 11
federal sentence must be found by a jury, in the absence of any 12
waiver of rights by the defendant." Id. at 24 (citing Jones and 13
Apprendi). Where "[t]he state statute requires no finding of 14
generic burglary, and without a charging document that narrows 15
the charge to generic limits, the only certainty of a generic 16
finding lies . . . (in a pleaded case) in the defendant's own 17
admissions or accepted findings of fact confirming the factual 18
basis for a valid plea." Id. at 25. Were the sentencing judge, 19
in considering the ACCA enhancement, to "make a disputed finding 20
of fact about what the defendant and state judge must have 21
understood as the factual basis of the prior plea," the 22
factfinding would raise the constitutional concern underlying 23
Jones and Apprendi. Id. 24
In Shepard, the Court concluded that the fact in 25
question -- whether Shepard had broken into the buildings 26

-- 20 of 40 --

21
described in the police reports or complaint applications -- even 1
though it was undisputed by the defendant, was "too far removed 2
from the conclusive significance of a prior judicial record, and 3
too much like the findings subject to Jones and Apprendi." Id. 4
The plurality therefore would have limited the permissible 5
sources of judicial factfinding to exclude police reports and 6
complaint applications in order, in part, to avoid the risk of 7
unconstitutionality. Id. at 25-26. 8
Shepard teaches that the sentencing court cannot make 9
its own finding of fact regarding whether a prior conviction 10
qualifies as a "violent felony" (or "serious drug offense") under 11
the ACCA. Id. at 21 (majority opinion) (noting, and later 12
rejecting, the government's argument for allowing a sentencing 13
court to rely on documents beyond "conclusive records made or 14
used in adjudicating guilt"). The sentencing court must rely on 15
evidence from the record of conviction to determine whether the 16
"earlier guilty plea [in question] necessarily admitted, and 17
supported a conviction for," a "violent felony," id. at 16; if 18
such evidence is not available, then the government has not met 19
its burden to demonstrate that the prior conviction was a 20
"violent felony." Speculation based on inferences is misplaced 21
in light of the Supreme Court's concern about establishing with 22
"certainty" that a prior conviction is a predicate crime under 23
the ACCA. See id. at 21-22 (discussing Taylor's "demand for 24
certainty"). 25

-- 21 of 40 --

22
The Shepard Court indicated that documents relating to 1
the plea itself -- "a transcript of a plea colloquy or . . . 2
written plea agreement presented to the court, or . . . a record 3
of comparable findings of fact adopted by the defendant upon 4
entering the plea" -- would be "the closest analogs" to the 5
judicial record evidence approved in Taylor. Id. at 20. These 6
analogs were different from the pre-state-plea documents -- 7
police reports and complaint applications -- that the government 8
had urged the Shepard district court to consider. 9
Here, the government urged the district court to look 10
to one pre-state-plea document, the Bill of Particulars, and to 11
other post-state-plea documents, documents relating not to the 12
taking of Rosa's plea in State Supreme Court, but to his 13
sentencing there. The district court relied upon (1) the Bill of 14
Particulars filed in the state case (pre-plea), (2) the State PSR 15
(post-plea), (3) the state sentencing transcript (post-plea), and 16
(4) the Federal PSR prepared in this case in determining the 17
factual basis of Rosa's 1991 conviction (post-plea). It also (5) 18
drew logical inferences about facts underlying an affirmative 19
defense that Rosa waived by virtue of his plea. Sentencing Tr. 20
at 25; see also Sentencing Mem. at 8-9. 21
We pause to note that the Shepard Court was apparently 22
concerned about the prospect of a sentencing court making any 23
factual finding not necessarily implied by the prior 24
conviction -- irrespective of how clearly the factual finding was 25
established. The State PSR here reveals a disputed assertion of 26

-- 22 of 40 --

23
fact: whether the "gun" was a "firearm." But Shepard, by 1
concluding that it did not matter whether the defendant in that 2
case disputed that he had broken into the buildings in question 3
and thereby committed a "generic" burglary, Shepard, 544 U.S. at 4
19, implies that it does not matter here whether the assertion 5
that the 1991 crime of conviction involved a firearm was disputed 6
or not. 7
For us to affirm the district court's conclusion that 8
the "gun" was a firearm, then, the documents and inferences that 9
the district court used to reach this conclusion must qualify as 10
"Shepard evidence," in this case, documents that show that the 11
"earlier guilty plea necessarily admitted, and supported a 12
conviction for," id. at 16, an offense "involving the use or 13
carrying of a firearm," 18 U.S.C. § 924(e)(2)(B). We conclude 14
that they do not. 15
A. The Bill of Particulars 16
The Bill of Particulars filed by the People in support 17
of the 1991 Indictment included the statement that a "small .22 18
cal. type gun," which the government intended to prove at trial 19
was used in the crime, was not recovered and therefore would not 20
be submitted as physical evidence at trial, and described the 21
conduct that the People intended to prove at trial as involving 22
"a gun." The district court, in sentencing Rosa, incorporated by 23
reference the government's Sentencing Memorandum which made 24
reference to the Bill of Particulars. But since no mention of it 25
was made in the government's presentation to us, we asked the 26

-- 23 of 40 --

11 The principle that "[i]ssues not sufficiently argued in
the briefs are considered waived and normally will not be
addressed on appeal," Norton v. Sam's Club, 145 F.3d 114, 117 (2d
Cir. 1998), is applicable to criminal cases, see United States v.
Crispo, 306 F.3d 71, 86 (2d Cir. 2002).
24
parties for, and received, supplemental briefing on whether the 1
Bill of Particulars is a "charging document" under Shepard from 2
which the district court might have concluded that what "appeared 3
to be a pistol" was in fact a "firearm" under the ACCA. We 4
conclude that, assuming that the issue has not been waived by the 5
government,11 the Bill of Particulars does not satisfy the 6
requirements of Shepard. 7
We assume for purposes of this discussion that the Bill 8
of Particulars may best be characterized as a "charging 9
document." We are not convinced, notwithstanding the Shepard 10
Court's reference to "charging document[s]" as potentially 11
reliable indicia of the nature of prior convictions, that the 12
Bill is therefore "Shepard evidence" for our purposes. See 13
Shepard, 544 U.S. at 26. Rosa did not stand trial. The Bill of 14
Particulars did not help define the crime of which he was 15
convicted, see Taylor, 495 U.S. at 602, or serve to limit the 16
charges that he could have pleaded guilty to, see Shepard, 544 17
U.S. at 21. At most, the Bill of Particulars limited only what 18
the State would have been allowed to prove against Rosa had the 19
case gone to trial. See, e.g., People v. Greaves, 1 A.D.3d 979, 20
980, 767 N.Y.S.2d 530, 531-32 (4th Dep't 2003) (reversing rape 21
conviction because of violation of the "defendant's 'fundamental 22

-- 24 of 40 --

25
and nonwaivable' right to be tried on only those crimes charged 1
in the indictment . . . as limited by the bill of particulars"). 2
Rosa admitted at his plea allocution to having acted in 3
concert with and aided and abetted people who had displayed "what 4
appeared to be a handgun." 1991 Plea Tr. at 16 (emphasis added). 5
His plea of guilty to Count One was an admission of that with 6
which he was charged -- aiding and abetting and acting in concert 7
with others in "forcibly steal[ing] property from another person" 8
in the course of which one of the perpetrators "display[ed] . . . 9
what appeared to be a handgun." Id. (emphasis added). But 10
nothing he said constituted an admission of the use by anyone in 11
any way of a firearm in connection with the crime. 12
To be sure, the Bill of Particulars referred to a 13
"small .22 cal. type gun" that was not recovered -- and therefore 14
would not be submitted as physical evidence at trial as a 15
"[w]eapon[] used in the crime" -- but that the People intended to 16
demonstrate had been used by the co-defendants during the course 17
of the robbery. Perhaps the People would have established such 18
use had a trial taken place. But there was no trial. And Rosa, 19
in pleading guilty, pleaded only to participating in a robbery 20
involving "what appeared to be a handgun." During the State 21
Probation Office interview, he expressly stated that a BB gun, 22
which is not a firearm, was used. We therefore cannot conclude 23
that Rosa necessarily pleaded to a crime involving the use of a 24
firearm, regardless of the allegations in the Bill of 25
Particulars. 26

-- 25 of 40 --

26
Our conclusion may be in tension with those of two of 1
our sister circuits. In United States v. Simms, 441 F.3d 313 2
(4th Cir.), cert. denied, --- U.S. ---, 127 S. Ct. 233 (2006), 3
the Fourth Circuit approved a district court's reliance on a 4
victim's statement because it was "later explicitly incorporated 5
into Maryland's statement of charges against Simms." Id. at 317. 6
"Taylor and Shepard specifically allow district courts to 7
consider charging documents in determining the nature of prior 8
convictions." Id. We do not disagree. But we do not think, nor 9
did the Fourth Circuit say or imply, that the characterization of 10
evidence as a "charging document" concludes the inquiry. On the 11
facts before us, even accepting that the Bill of Particulars was 12
a "charging document," as we do for these purposes, we do not 13
think that Rosa pleaded guilty to, or otherwise admitted the 14
allegations contained in the Bill; thus, he did not necessarily 15
plead to a charge involving a firearm. It may well be that 16
Simms, in pleading guilty to the charges against him, did, by 17
contrast, allocute to the factual elements that the witness 18
described and that were later incorporated by the state in its 19
statement of charges. 20
In United States v. Jones, 453 F.3d 777 (6th Cir.), 21
cert. denied, --- U.S. ---, 127 S. Ct. 611 (2006), the Sixth 22
Circuit concluded that 23
An affidavit of complaint is a type of record 24
that a district court can properly rely on in 25
determining the nature of predicate offenses, 26
consistent with the standards of Shepard. 27
Complaints are judicial documents, filed 28

-- 26 of 40 --

27
under oath and submitted in furtherance of 1
formal prosecution. They bear, accordingly, 2
substantially greater indicia of reliability 3
than mere police reports, which are not filed 4
in court, are not sworn to, and are developed 5
for an investigatory purpose. 6
Id. at 780 (citation omitted). As we have said, we do not think 7
that every document properly classified as a charging document in 8
a state case to which a defendant pleads guilty is ipso facto 9
probative on the issue of whether the defendant necessarily 10
pleaded guilty to a "violent felony." And we do not think, as 11
the Jones court seemed to indicate, that the question before us 12
is whether the unsworn Bill of Particulars "bear[s] . . . indicia 13
of reliability." The dispositive question is "whether the 14
plea . . . 'necessarily' rested on the fact," Shepard, 544 U.S. 15
at 21, that the crime to which Rosa pleaded "involv[ed] the use 16
or carrying of a firearm." We do not think that it did. 17
We conclude that the Bill of Particulars, even if a 18
charging document, was not one upon which the district court 19
could rely in concluding that the defendant pleaded guilty in 20
state court in 1991 to a felony involving a firearm. It 21
therefore could not support the district court's application of 22
the ACCA to Rosa. 23
B. Federal PSR 24
The Federal PSR cannot satisfy Shepard either. See 25
United States v. Turbides-Leonardo, 468 F.3d 34, 39 (1st Cir. 26
2006) ("[A] presentence report in a subsequent case ordinarily 27
may not be used to prove the details of the offense conduct that 28
underlies a prior conviction."); United States v. Garza-Lopez, 29

-- 27 of 40 --

28
410 F.3d 268, 274 (5th Cir. 2005) ("[U]nder Shepard, a district 1
court is not permitted to rely on a PSR's characterization of a 2
defendant's prior offense for enhancement purposes."). That the 3
Federal PSR relies entirely on the State PSR for the fact of the 4
involvement of a firearm further undermines the ability of the 5
district court to use it to establish the nature of the crime to 6
which Rosa pleaded guilty. See Shepard, 544 U.S. at 23. 7
Some circuits have held that a sentencing court may 8
look to a PSR prepared for that case to determine the underlying 9
facts of a previous conviction when the defendant fails to object 10
to the PSR's findings, and thereby assents to those facts. See, 11
e.g., United States v. Siegel, 477 F.3d 87, 93-94 (3d Cir. 2007) 12
(concluding that the defendant's failure to object in the 13
sentencing court and on appeal to the factual description of his 14
prior conviction in the PSR amounts to an adoption of the factual 15
record included therein, and "that the facts averred in the PSR 16
acceded to by Siegel avoid the 'collateral trial,' and 'judicial 17
factfinding' preempted by the Court's holding in Shepard"); 18
United States v. Cullen, 432 F.3d 903, 905 (8th Cir. 2006) ("By 19
not objecting to the PSR's factual allegations, [the defendant] 20
has admitted them." (citation omitted)). We need not decide 21
whether we would adopt such a rule. Although Rosa failed to 22
lodge any objection to the PSR directly with the probation 23
office, he submitted a sentencing memorandum to the district 24
court dated May 11, 2005, specifically objecting to the PSR's 25
findings regarding the 1991 conviction. We therefore cannot 26

-- 28 of 40 --

12 See Gov't Br. at 29 ("[U]nder the Supreme Court's
decisions in Shepard and Taylor, it is not at all clear that the
District Court is permitted to consult the State Presentence
Report on its own terms . . . .").
29
conclude that Rosa admitted the findings in the Federal PSR by 1
failing to object to them. 2
C. The State PSR 3
As discussed, the State PSR prepared following Rosa's 4
1991 conviction cited conflicting evidence about the nature of 5
the object used during the robbery. It contained a victim's 6
statement that during the robbery the victim "felt and observed a 7
black handgun pressed into his stomach," and a witness's 8
statement that one of the perpetrators was "holding what appeared 9
to be a black automatic handgun." But it also contained a 10
statement by Rosa that Rosa's co-defendant "apparently had in his 11
possession a BB gun" -- which is not a firearm under the ACCA. 12
The State PSR itself, then, seems to reflect a disputed issue of 13
fact as to the nature of the object used during the robbery. 14
We have not yet addressed whether, in light of Shepard, 15
a district court may look to facts about the nature of the 16
offense presented in a state presentence report in determining 17
whether a prior conviction constitutes a "violent felony" under 18
the ACCA. The fact that the State PSR quotes the victim or a 19
witness making references to a handgun does not establish, the 20
government agrees, that Rosa "necessarily" pleaded to an offense 21
involving a firearm, as Shepard requires.12 This is especially 22
so where, as here, the State PSR also describes a statement 23

-- 29 of 40 --

13 If a state presentence report were adopted by the state
trial court without objection by the defendant, Shepard's
requirement that the defendant "assent" to the factual findings
of the trial court for purposes of an inquiry under the ACCA
might be met. But the record indicates neither that the district
court explicitly adopted the findings in the State PSR, nor that
Rosa assented to such findings. Because the district court did
not explicitly adopt any of these findings, we do not think that
Rosa's failure to raise the issue of the PSR's conflicting
reports as to the nature of the object used in the robbery
constitutes an admission of any kind. Moreover, because the
issue during the plea colloquy concerned who was holding the
object, not the nature of the object, it is understandable that
no one made a specific finding or objection as to whether the
object used was a firearm.
30
disputing the victim's assertions. See Shepard, 544 U.S. at 21; 1
see also United States v. Grier, 475 F.3d 556, 603 (3d Cir. 2007) 2
(en banc) (Sloviter, J., dissenting) ("I submit that after 3
Shepard, a presentence report without more cannot be the basis 4
for a finding of an offense that is the predicate for a sentence 5
enhancement."). The government relies on the State PSR, instead, 6
to prove those facts described in the State PSR that were 7
"explicitly adopted by the trial judge to which Rosa assented." 8
Gov't Br. at 29. As we discussed in the next section, however, 9
we disagree with the government's view that the relevant facts in 10
the State PSR were "explicitly adopted by the trial judge" or 11
assented to by Rosa.13
12
The State PSR here does not provide a basis for 13
determining the nature of the defendant's conduct any better than 14
does a police report, which, the Shepard Court ruled, "do[es] not 15
define the conduct to which a defendant eventually pleads 16
guilty." United States v. Green, 480 F.3d 627, 632 (2d Cir. 17

-- 30 of 40 --

31
2007) (applying Shepard). To begin with, it appears that the 1
State PSR drew its descriptions of statements by the victim and 2
bus-driver witness directly from the police reports rather than 3
an independent investigation. See State PSR at 2 (noting 4
dependence of descriptions on "City of New Rochelle Police 5
Department records"). Like the police reports in Shepard, 6
neither the police reports from which the State PSR drew support 7
nor the accounts of the nature of the object used in the offense 8
were "mentioned at [Rosa's] pleas" or "read by the judge to 9
[Rosa] during the plea colloquy." Shepard, 544 U.S. at 18. Rosa 10
was never "asked if the information contained in the [PSR] w[as] 11
true." Id. (first brackets added); see id. ("Shepard . . . 12
stated 'that none of the details in th[e police] reports w[as] 13
ever mentioned at his pleas,' that 'the reports themselves were 14
never read by the judge to him during the plea colloquy,' and 15
that at no time 'was he ever asked if the information contained 16
in the . . . [police] [r]eports w[as] true.'" (third brackets 17
added; citation to district court opinion omitted)). To the 18
extent that the district court relied on the State PSR itself to 19
support its conclusion that a firearm was used in the 1991 20
robbery, such reliance was misplaced. 21
D. The State Trial Sentencing Transcript 22
The government concedes that the State PSR, without 23
more, is unlikely to satisfy Shepard. It argues, however, that 24
where a state trial court adopts the factual findings of a state 25
presentence report, a defendant's failure to object to those 26

-- 31 of 40 --

32
factual findings amounts to an assent by the defendant to those 1
facts. Extending this argument to the state sentencing 2
transcript, the government also does not contend that the 3
transcript, alone, is Shepard evidence. It asserts that in this 4
case, it satisfies the Shepard requirements because Rosa 5
"assented" to that court's statements suggesting that a firearm 6
was used in the robbery. 7
The Shepard Court ruled that in determining whether a 8
prior plea of guilty admitted a particular fact, a district court 9
is generally "limited to examining the statutory definition, 10
charging document, written plea agreement, transcript of plea 11
colloquy, and any explicit factual finding by the trial judge to 12
which the defendant assented." Shepard, 544 U.S. at 16 (emphasis 13
added). The government here points to the state judge's 14
statement at sentencing that "[Rosa] was not the one who wielded 15
the gun," and contends that this constituted a factual finding by 16
the judge that the wielded object was in fact a gun. It further 17
argues that Rosa assented to this "finding," both because he did 18
not dispute the characterization of the object as a gun and 19
because his lawyer stated that "it was not Eduardo who had the 20
gun in this particular incident." We disagree. 21
In Shepard, the Court stated that the most appropriate 22
sources for the district court to consult to determine whether a 23
given fact was necessarily established "in pleaded cases" are 24
"the statement of factual basis for the charge, Fed. Rule Crim. 25
Proc. 11(a)(3), shown by a transcript of plea colloquy or by 26

-- 32 of 40 --

33
written plea agreement presented to the court, or by a record of 1
comparable findings of fact adopted by the defendant upon 2
entering the plea. With such material in a pleaded case, a later 3
court could generally tell whether the plea had 'necessarily' 4
rested on the fact" at issue. Shepard, 544 U.S. at 20-21 5
(emphases added). The Court's repeated reference to the plea 6
stage reflects both the conclusive effect of a plea as an 7
adjudication of the defendant's guilt and the judicial care that 8
goes into the court's acceptance of a plea. See generally Von 9
Moltke v. Gillies, 332 U.S. 708, 719 (1948) ("A plea of guilty 10
differs in purpose and effect from a mere admission or an 11
extrajudicial confession; it is itself a conviction. . . . Out 12
of just consideration for persons accused of crime, courts are 13
careful that a plea of guilty shall not be accepted unless made 14
voluntarily after proper advice and with full understanding of 15
the consequences.'" (quoting Kercheval v. United States, 274 U.S. 16
220, 223 (1927))). 17
At the joint plea hearing for Rosa and Warren, with 18
both defendants placed under oath, the court was indeed careful 19
to determine that they understood what it was they were 20
admitting. No question was raised as to whether the object with 21
which the defendants had threatened the victim was in fact a gun, 22
because a conviction of First Degree Robbery required only that 23
the object appeared to be a gun. Instead, the questioning at the 24
plea hearing focused on who held the object; and the object was 25
unvaryingly referred to by the court as "what appeared to be" a 26

-- 33 of 40 --

34
gun. Thus, the court asked, "Mr. Rosa, do you freely and 1
voluntarily admit that . . . you did display what appeared to be 2
a pistol, revolver, or other firearm . . . ?" 1991 Plea Tr. at 3
14-15 (emphasis added). After Rosa's counsel interposed that 4
Rosa could admit only to aiding and abetting, not to displaying, 5
the court asked Rosa, "And do you admit that while aiding and 6
abetting . . . you did display what appeared to be a pistol, 7
revolver, or other firearm . . . ?" Id. at 15 (emphasis added). 8
When Rosa responded "Not me," the court asked, "So while you 9
yourself may not have possessed what appeared to be a 10
handgun, . . . was one displayed by the people with whom you were 11
acting in concert and aiding and abetting?" Id. (emphasis 12
added). The court had used this same careful term for the 13
displayed object in conducting the allocution of Warren. See id. 14
at 14 ("Mr. Warren, do you freely and voluntarily admit 15
that . . . you did display what appeared to be a pistol, 16
revolver, or other firearm . . . ?" (emphasis added)). The court 17
never asked either Rosa or Warren whether what was displayed was 18
in fact a gun. And after it had concluded its questioning of 19
Rosa and Warren, the court noted that "they have been asked very 20
specific questions." Id. at 17. 21
In light of the state court's punctilious framing of 22
the "very specific questions" to be answered before he accepted 23
the pleas of guilty, inquiring not whether the object displayed 24
was a gun but only whether it "appeared to be" a gun, it would be 25
unreasonable to infer that his statement at sentencing that he 26

-- 34 of 40 --

35
was imposing a lenient sentence on Rosa because Rosa "was not the 1
one who wielded the gun," was intended to constitute a finding 2
that what had been wielded was in fact a gun. Such an offhand, 3
or shorthand, reference is not the manner in which careful judges 4
make findings, and we cannot conclude that this reference falls 5
within the scope of what Shepard meant by "an[] explicit factual 6
finding by the trial judge." 7
Put another way, we do not think that Rosa's failure to 8
object when the state court said that "[Rosa] was not the one who 9
wielded the gun" qualifies as an admission by silence. We have 10
said that "an admission by silence is admissible [as evidence] if 11
'there are circumstances which render it more reasonably probable 12
that a man would answer the charge made against him than that he 13
would not.'" United States v. Aponte, 31 F.3d 86, 87 (2d Cir. 14
1994) (citations omitted). The state court made its statement in 15
the course of giving Rosa a lesser sentence because he was not 16
the one holding "the gun." We hardly think that the statement 17
"charged" Rosa. Cf. id. ("[A] person ordinarily will respond to 18
an incriminatory or defamatory statement with a denial . . . ." 19
(citation omitted)). And we do not think it "more reasonably 20
probable" that someone in Rosa's position would have contradicted 21
the judge at that moment to insist that the object that he was 22
not holding was not a firearm. 23
For all of these reasons, we conclude that the district 24
court was not able to rely on the state sentencing transcript to 25
find that Rosa's crime or act of delinquency involved a firearm. 26

-- 35 of 40 --

36
E. Logical Inference from the Guilty Plea 1
Without any sufficiently reliable records from the 2
state proceedings, the linchpin of the government's argument is 3
its interpretation of the logical consequences of Rosa's guilty 4
plea to First Degree Robbery. The government contends that the 5
defendant's guilty plea to Robbery in the First Degree rather 6
than to Robbery in the Second Degree in the 1991 proceedings 7
necessarily means that he admitted that the crime involved a 8
firearm. Gov't Br. at 24-27, 29. 9
The government's logic is as follows: The elements of 10
subsection (4) of Robbery in the First Degree are identical to 11
the elements of Robbery in the Second Degree under subsection 12
(2)(b). Compare N.Y. Penal Law § 160.15(4) (First Degree) ("A 13
person is guilty of robbery in the first degree when he forcibly 14
steals property and when, in the course of the commission of the 15
crime or of immediate flight therefrom, he or another participant 16
in the crime . . . . [d]isplays what appears to be a pistol, 17
revolver, rifle, shotgun, machine gun or other firearm . . . .") 18
with id. § 160.10(2)(b) (Second Degree) ("A person is guilty of 19
robbery in the second degree when he forcibly steals property and 20
when . . . [i]n the course of the commission of the crime or of 21
immediate flight therefrom, he or another participant in the 22
crime . . . [d]isplays what appears to be a pistol, revolver, 23
rifle, shotgun, machine gun or other firearm . . . ."). Insofar 24
as Rosa's case was concerned, the only difference between the 25
two, which defines their relationship to one another, is that a 26

-- 36 of 40 --

37
person accused of Robbery in the First Degree can assert, as an 1
affirmative defense, that "such pistol, revolver, rifle, shotgun, 2
machine gun or other firearm was not a loaded weapon from which a 3
shot, readily capable of producing death or other serious 4
physical injury, could be discharged." Id. § 160.15(4). If the 5
defendant can establish that affirmative defense, the alleged 6
crime is reduced to Robbery in the Second Degree. The government 7
asserts that here, by pleading guilty to first degree robbery, 8
Rosa waived this affirmative defense. And by doing so, Rosa 9
necessarily conceded that the weapon was a firearm. 10
We find the government's argument unpersuasive. Rosa 11
pleaded guilty, as reflected by the plea colloquy, to a crime 12
that included only the "display [of] what appeared to be . . . a 13
handgun." 1991 Plea Tr. at 16. When charging a defendant with 14
"robbery in the first degree (displayed)" in New York, the 15
state's burden is not "to introduce into evidence the weapon used 16
in the robbery; nor [need it] present evidence that the weapon 17
was loaded or capable of being fired." People v. Padua, 297 18
A.D.2d 536, 539, 747 N.Y.S.2d 205, 208 (1st Dep't 2002). 19
"Instead, 'Penal Law § 160.15(4) merely requires the prosecution 20
to prove that the defendant or another participant displayed what 21
appeared to a be pistol, revolver or other firearm.'" Id. 22
(citations omitted). By pleading guilty, Rosa admitted that the 23
State had carried this burden. On an affirmative defense, by 24
contrast, the defendant bears the burden of proof. See N.Y. 25
Penal Law § 25.00(2) ("When a defense declared by statute to be 26

-- 37 of 40 --

38
an 'affirmative defense' is raised at a trial, the defendant has 1
the burden of establishing such defense by a preponderance of the 2
evidence."). 3
We are not convinced that by agreeing to plead guilty 4
to Robbery in the First Degree, and therefore not asserting the 5
affirmative defense that the object used during the crime was not 6
a firearm, Rosa was conceding that he would have been unable to 7
carry his burden of proving this affirmative defense had he 8
decided to raise it at trial. First, in order to carry this 9
burden, it seems that Rosa would have been required to go to 10
trial and accept its additional expense and risks. As a 11
practical matter, a principal goal of pleading guilty is to avoid 12
trial, and the desire not to bear the costs of trial should not 13
be a ground for an inference that the party could not prevail at 14
trial. It is doubtful that the State would agree that its own 15
abandonment of three other charges against Rosa in exchange for 16
his agreement to plead guilty to First Degree Robbery could be 17
viewed as an implicit concession that it could not carry its 18
burden of proving these abandoned counts. 19
Second, Padua, which involved a BB gun in evidence and 20
an alleged second, unintroduced, gun that was "real," suggests 21
that the affirmative defense here comes into play only if the 22
object -- whether "real" gun or BB gun -- was unloaded or 23
inoperable. See Padua, 297 A.D.2d at 539, 747 N.Y.S.2d at 208 24
("[T]he affirmative defense to robbery in the first degree comes 25
into play only when it is demonstrated by a preponderance of the 26

-- 38 of 40 --

39
evidence that the gun was unloaded or inoperable -- and there was 1
no such evidence offered in this case with respect to either 2
gun."). Therefore, if the object in Rosa's incident was a BB 3
gun, and hence was not a firearm within the meaning of ACCA, Rosa 4
could not have established the affirmative defense under 5
§ 160.15(4) if the BB gun was loaded. For this reason too, his 6
decision to forgo any attempt to establish the affirmative 7
defense does not necessarily imply that what was involved was a 8
real gun. 9
We doubt, moreover, that Shepard and, as the plurality 10
in Shepard suggested, Apprendi, allow such an inference to be 11
drawn. The waiver argument would permit the government to 12
circumvent Shepard's requirement that district courts limit their 13
consideration to particular documents that can identify the 14
underlying facts of a prior conviction with certainty. 15
We think that the fundamental problem underlying the 16
district court's reliance on inferences from waiver of an 17
affirmative defense, or on the Bill of Particulars, the Federal 18
PSR, the State PSR, the state sentencing transcript, or any other 19
part of the state record, for its conclusion that the "gun" 20
involved was a firearm is precisely the fact that the district 21
court looked to the evidence before it and drew its own 22
inferences rather than determining what inferences were compelled 23
by the state record of conviction. See Sentencing Tr. at 25 24
("find[ing] that the record here supports . . . that the 25
defendant is a career criminal under the Guidelines"). 26

-- 39 of 40 --

40
Permitting a district court to make such factual findings thus 1
threatens to violate the Jones-Apprendi constitutional rule that 2
"any fact other than a prior conviction sufficient to raise the 3
limit of the possible federal sentence must be found by a jury, 4
in the absence of any waiver of rights by the defendant." 5
Shepard, 544 U.S. at 24 (opinion of Souter, J.). Unlike the 6
police reports that the majority in Shepard refused to permit the 7
district court to consult, which, according to the Shepard 8
dissenters, "ma[de] inescapable the conclusion that, at each 9
guilty plea, Shepard understood himself to be admitting the crime 10
of breaking into a building," id. at 31 (O'Connor, J., 11
dissenting), we think it clear from the plea transcript that 12
neither Rosa nor the court understood Rosa to be admitting that 13
what was displayed was an actual firearm. Thus, the evidence the 14
district court relied on here seems less reliable than that on 15
which the district court relied in Shepard, and which the Supreme 16
Court found unsound. The district court's conclusion that Rosa 17
was subject to the ACCA's fifteen-year mandatory minimum 18
therefore relied on an improper factual finding based on evidence 19
outside the scope of what is permitted by Shepard. 20
CONCLUSION 21
For the foregoing reasons, we vacate Rosa's sentence 22
and remand for resentencing. 23

-- 40 of 40 --