The Honorable Edward R. Korman, of the United States District Court for the Eastern… v. United States UNITED STATES COURT OF APPEALS 1 2 FOR THE SECOND CIRCUIT 3 4 August…

*The Honorable Edward R. Korman, of the United States
District Court for the Eastern District of New York, sitting by
designation.
1
05-6662-pr
Zhang v. United States
UNITED STATES COURT OF APPEALS 1
2
FOR THE SECOND CIRCUIT 3
4
August Term, 2006 5
6
(Argued: January 11, 2007 Decided: October 23, 2007) 7
8
Docket No. 05-6662-pr 9
- - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 10
11
SEAN ZHANG, 12
13
Petitioner-Appellee, 14
15
v. 16
17
UNITED STATES OF AMERICA, 18
19
Respondent-Appellant. 20
21
- - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 22
23
B e f o r e: WINTER, CABRANES, Circuit Judges, and KORMAN, 24
District Judge.*
25
26
Appeal from an order of the United States District Court for 27
the Eastern District of New York (Arthur D. Spatt, Judge) 28
granting a petition for habeas corpus relief under 28 U.S.C. § 29
2255. Petitioner-appellee, a legal permanent resident of the 30
United States, pled guilty to one count of mail fraud under 18 31
U.S.C. § 1341. The district court found that statements of the 32
magistrate judge and prosecutor about the immigration 33
consequences of the conviction affirmatively misled the 34

-- 1 of 16 --

2
petitioner-appellee, thus rendering his guilty plea involuntary. 1
We find that the statements of the magistrate judge and 2
prosecutor -- while not full explanations -- were not 3
sufficiently misleading to render the guilty plea involuntary. 4
Accordingly, we vacate and remand for consideration of 5
petitioner-appellee’s other constitutional arguments. 6
GARY SCHOER, Syosset, New York, for 7
Petitioner-Appellee. 8
9
CARRIE CAPWELL, Assistant United 10
States Attorney (Roslynn R. 11
Mauskopf, United States Attorney 12
for the Eastern District of New 13
York, on the brief, and Peter A. 14
Norling, Assistant United States 15
Attorney, of counsel), United 16
States Attorney’s Office for the 17
Eastern District of New York, 18
Brooklyn, New York, for Respondent- 19
Appellant. 20
21
WINTER, Circuit Judge: 22
The government appeals Judge Spatt’s order granting Sean 23
Zhang’s 28 U.S.C. § 2255 petition for habeas corpus and vacating 24
his plea of guilty to mail fraud and resultant sentence of 60 25
months’ imprisonment. Judge Spatt found that Zhang’s guilty plea 26
was involuntary because the magistrate judge and the prosecutor 27
had affirmatively misled Zhang during the plea colloquy with 28
respect to the likelihood of his being deported as a result of 29
his conviction. Zhang v. United States, 401 F.Supp.2d 233, 243- 30
44 (E.D.N.Y. 2005) (“Zhang I”). On appeal, the government 31
principally argues that the representations of the magistrate 32

-- 2 of 16 --

3
judge and prosecutor -- that Zhang faced possible, rather than 1
certain, deportation -- were not affirmatively misleading or 2
prejudicial, and that the court had no greater obligation to 3
spell out the possible collateral effects of Zhang’s guilty plea. 4
We conclude that the statements made during the colloquy 5
were not affirmatively misleading, and that they did not render 6
Zhang’s guilty plea involuntary. We therefore vacate the order 7
below. Zhang has also raised a claim of ineffective assistance 8
of counsel, which we remand to the district court for further 9
proceedings. 10
BACKGROUND 11
Sean Zhang came to the United States from China in 1985, at 12
the age of seven. Zhang I, 401 F.Supp.2d at 235. Zhang’s family 13
was granted asylum on the basis of his father’s public criticism 14
of Communism and the Chinese government. Id. Zhang attended 15
Cornell University and graduated with a Bachelor of Science 16
degree in “Food Science.” Id. Although Zhang has spent the bulk 17
of his life in the United States, does not speak Chinese 18
proficiently, is married to an American citizen, and has long 19
been a legal permanent resident, he has never become an American 20
citizen. Id. 21
In 2001, while working as a chemist, Zhang began mixing and 22
selling capsules of the chemical 2,4 Dinitrophenol (“DNP”). Id. 23
In addition to its many industrial and research uses, DNP, when 24

-- 3 of 16 --

4
ingested by humans, acts as a metabolic stimulant and can reduce 1
body fat. Id. Because of the effect of DNP, the drug is banned 2
for human use by the Food and Drug Administration. Id. 3
Nonetheless, DNP is sometimes used by bodybuilders seeking to 4
quickly reduce their body fat. Id. Using the screen name “DNP 5
Guru,” Zhang used a bodybuilding website to promote and sell DNP. 6
Id. One of Zhang’s customers, Eric Perrin, died as a result of 7
ingesting DNP purchased from Zhang. Id. Another customer, James 8
Shull, lapsed into a 10-day coma caused by DNP prepared and sold 9
by Zhang. Id. 10
Zhang was indicted on ten counts of introducing a misbranded 11
drug into interstate commerce, in violation of 21 U.S.C. § 12
331(a), and ten counts of mail fraud, in violation of 18 U.S.C. § 13
1341. Zhang entered into a plea agreement in which he agreed to 14
plead guilty to a single count of mail fraud with a maximum 15
penalty of 60 months and waive his right to appeal if sentenced 16
to 60 months or less. The plea agreement stated that the 17
government would seek an upward departure based upon Perrin’s 18
death and Shull’s injuries, and included the statement, “Other 19
penalties: Removal.” The plea agreement also contained the 20
government’s loss estimate of between $70,000 and $120,000. 21
According to Zhang, in discussing a guilty plea, his 22
attorney told him that any resulting deportation proceeding would 23
be discretionary, and that deportation was unlikely given his 24

-- 4 of 16 --

5
personal history and family circumstances. On June 25, 2002, 1
Zhang entered his guilty plea before a magistrate judge. During 2
the plea allocution, the prosecutor stated that Zhang “agrees he 3
[is] subject to possible post sentence deportation.” Plea Tr. at 4
14. The magistrate judge further stated that “it’s not indicated 5
as a consequence of your plea and the plea agreement but the 6
government indicated that this felony conviction because of your 7
immigration status could result in your deportation. Do you 8
understand that?” Zhang answered “Yes, I understand.” Id. at 9
15. Elsewhere in the allocution, the prosecutor noted that 10
Zhang’s counsel had reserved the right to move for a downward 11
departure, and to challenge any loss calculation. 12
A year later, following a hearing pursuant to United States 13
v. Fatico, 579 F.2d 707 (2d Cir. 1978), Zhang was sentenced to 60 14
months’ imprisonment plus three years’ supervised release, and 15
ordered to pay $113,414.53 in restitution. At the sentencing 16
hearing, the prosecutor noted that “there is another condition of 17
supervised release. He may be deported. If he does, if you can 18
put on the judgment that he should not reenter without the 19
permission of the Attorney General.” Sentencing Tr. at 410. The 20
sentencing judge agreed, and stated that “if the defendant is 21
deported, he’s not to reenter the United States illegally without 22
the consent of the government.” Id. 23
Pursuant to his plea agreement, Zhang did not appeal his 24

-- 5 of 16 --

6
conviction or sentence. After the time for filing a direct 1
appeal had passed, Zhang received a Notice to Appear from the 2
Bureau of Immigration and Customs Enforcement (“ICE”). Zhang 3
claims at this time that he first became aware that he faced 4
mandatory deportation as a result of having been convicted of an 5
“aggravated felony” -- defined in relevant part for deportation 6
purposes as “an offense that involves fraud or deceit in which 7
the loss to the victim or victims exceeds $10,000.” 8 U.S.C. § 8
1101(a)(43)(M)(i). On June 17, 2004, Zhang filed a habeas corpus 9
petition in the district court pursuant to 28 U.S.C. § 2255, 10
seeking to vacate his conviction on two grounds: (i) that the 11
statements of the prosecutor and the court regarding possible 12
deportation were affirmatively misleading and violated Fed. R. 13
Crim. P. 11; and (ii) that he received ineffective assistance of 14
counsel regarding deportation. Zhang I, 401 F.Supp.2d at 236. 15
The government argued that the statements during the course of 16
sentencing were accurate because Zhang could potentially avoid 17
deportation by applying for asylum or relief under the Convention 18
Against Torture (“CAT”). 19
On July 29, 2005, the district court held a hearing on 20
whether Zhang’s guilty plea was involuntary because of the 21
characterization of the chances of deportation as less than 22
certain. Consideration of the ineffective assistance claim was 23
deferred. 24

-- 6 of 16 --

7
On November 18, 2005, the district court issued its decision 1
vacating Zhang’s conviction. Zhang I, 401 F.Supp.2d 233. The 2
court first held that Zhang’s claim was not procedurally barred 3
by his failure to raise it on direct appeal or by his plea 4
agreement’s waiver of collateral attack. Id. at 237. The court 5
then found that while Second Circuit law does not require a judge 6
to alert a defendant to the immigration consequences of a guilty 7
plea, affirmative misinformation about those consequences can 8
render a plea involuntary under Rule 11. Id. at 237-38. 9
Finally, the district court determined that it was, in fact, 10
materially misleading to inform Zhang that deportation was 11
“merely possible, not probably or certain,” and that “the 12
misrepresentation was sufficient to render Zhang’s plea 13
constitutionally involuntary.” Id. at 244. 14
The government appealed. 15
DISCUSSION 16
In appeals under 28 U.S.C. § 2255, “this Court reviews 17
factual findings for clear error and questions of law de novo.” 18
Harris v. United States, 367 F.3d 74, 79 (2d Cir. 2004) (internal 19
quotation marks omitted). 20
As a threshold issue, the government argues that Zhang 21
procedurally defaulted by failing to bring his claims on direct 22
appeal. “A motion under § 2255 is not a substitute for an 23
appeal.” United States v. Munoz, 143 F.3d 632, 637 (2d Cir. 24

-- 7 of 16 --

8
1998). In general, a claim may not be presented in a habeas 1
petition where the petitioner failed to properly raise the claim 2
on direct review. Reed v. Farley, 512 U.S. 339, 354 (1994). The 3
rule does not generally apply to claims of ineffective assistance 4
of counsel. Massaro v. United States, 538 U.S. 500, 505-06 5
(2003). The claim ruled on in the district court and before us 6
now, however, is not Zhang’s ineffective assistance of counsel 7
claim, but rather the claim that Zhang’s guilty plea was 8
involuntary. If such a claim has not been presented on direct 9
review, the procedural default bar may be overcome only where the 10
petitioner establishes either (1) “cause” for the failure to 11
bring a direct appeal and “actual prejudice” from the alleged 12
violations; or (2) “actual innocence.” Bousley v. United States, 13
523 U.S. 614, 622 (1998). “To satisfy the ‘cause’ requirement, 14
the petitioner must show circumstances ‘external to the 15
petitioner, something that cannot be fairly attributed to him.’” 16
Rosario-Dominguez v. United States, 353 F.Supp.2d 500, 508 17
(S.D.N.Y. 2005) (quoting Marone v. United States, 10 F.3d 65, 67 18
(2d Cir. 1993) and Coleman v. Thompson, 501 U.S. 722, 753 19
(1991)). 20
Zhang argues that because of the (mis)representations by the 21
court, his counsel, and the government about the deportation 22
consequences of his plea, he was unaware of those consequences 23
until he received a letter from the ICE, and that this serves as 24

-- 8 of 16 --

9
“cause” justifying his failure to bring the claim on direct 1
appeal. However, we cannot determine whether the allegedly 2
misleading statements prejudiced Zhang and excuse his failure to 3
bring his claims on direct appeal without first determining 4
whether they were, in fact, affirmatively misleading. If the 5
statements were affirmatively misleading and prejudicial, 6
procedural default would be waived and Zhang would prevail on the 7
merits. If the statements were not affirmatively misleading and 8
prejudicial, procedural default would not be waived, and Zhang 9
would lose on the merits. Either way, we must address the 10
merits. 11
Prior to accepting a guilty plea, a court must advise the 12
defendant of his right to plead not guilty and of the rights 13
waived by pleading guilty. Fed. R. Crim. P. 11(b)(1). Rule 11 14
also requires a court to tell the defendant of the possible 15
direct consequences of a guilty plea, such as the maximum prison 16
term, the maximum fine, and the effect of possible supervised 17
release. Id. A court need not, however, inform a defendant 18
about the “collateral” consequences of a guilty plea. See Michel 19
v. United States, 507 F.2d 461, 465 (2d Cir. 1974); Bye v. United 20
States, 435 F.2d 177, 179 (2d Cir. 1970) (“[A]n accused need not 21
be informed prior to the acceptance of his guilty plea about 22
every conceivable collateral effect the conviction entered on the 23
plea might have.”). 24

-- 9 of 16 --

10
The possibility of discretionary deportation after a guilty 1
plea is a “collateral” consequence that need not be addressed at 2
the plea hearing. Michel, 507 F.2d at 465-66. The passage of 3
the Illegal Immigration Reform and Immigrant Responsibility Act 4
of 1996 (“IIRIRA”) and the Antiterrorism and Effective Death 5
Penalty Act of 1996 (“AEDPA”), however, has altered the landscape 6
of immigration law, and deportation of aggravated felons is now 7
automatic and non-discretionary. 8 U.S.C. § 1227(a)(2)(A)(iii); 8
see also INS v. St. Cyr, 533 U.S. 289, 325 (2001) (referring to 9
deportation of aggravated felons as “certain”). Nonetheless, 10
several circuits have held that “automatic” deportation under 11
IIRIRA is still a collateral consequence that need not be 12
addressed prior to a court’s accepting a guilty plea. See El- 13
Nobani v. United States, 287 F.3d 417, 421 (6th Cir. 2002) (“[I]t 14
is clear that deportation is not within the control and 15
responsibility of the district court, and hence, deportation is 16
collateral to a conviction.”); United States v. Amador-Leal, 276 17
F.3d 511, 516-17 (9th Cir. 2002) (“[W]hether an alien will be 18
removed is still up to the INS. There is a process to go 19
through, and it is wholly independent of the court imposing 20
sentence . . . . Removal is not part of the sentence.”); and 21
United States v. Gonzalez, 202 F.3d 20, 27 (1st Cir. 2000) 22
(“However ‘automatically’ [the defendant’s] deportation . . . 23
might follow from his conviction, it remains beyond the control 24

-- 10 of 16 --

11
and responsibility of the district court in which that conviction 1
was entered and it thus remains a collateral consequence 2
thereof.”). 3
Although we have acknowledged the existence of the issue, 4
United States v. Cuoto, 311 F.3d 179, 190 (2d Cir. 2002), we have 5
not decided whether “automatic” deportation is a collateral 6
consequence of a guilty plea that need not be mentioned or a 7
direct consequence that required discussion during the plea 8
proceeding. Once again, the issue is not before us. As the 9
district court noted, “[w]hether automatic deportation is a 10
direct or collateral consequence is of no matter in this case 11
because the court did address deportation at the plea hearing.” 12
Zhang I, 401 F.Supp.2d at 239. We agree. 13
“Rule 11 sets forth requirements for a plea allocution and 14
is designed to ensure that a defendant’s plea of guilty is a 15
voluntary and intelligent choice among the alternative courses of 16
action open to the defendant.” United States v. Andrades, 169 17
F.3d 131, 133 (2d Cir. 1999) (internal quotation marks and 18
citation omitted). To successfully challenge a guilty plea 19
conviction based on a Rule 11 violation, a petitioner must 20
establish that the violation constituted a “constitutional or 21
jurisdictional” error, or establish that the error resulted in a 22
“complete miscarriage of justice,” or in a proceeding 23
“inconsistent with the rudimentary demands of fair procedure.” 24

-- 11 of 16 --

12
United States v. Timmreck, 441 U.S. 780, 783 (1979) (internal 1
quotation marks omitted). In addition, the petitioner must 2
demonstrate that the violation was prejudicial -- where the error 3
was not preserved, this requires the petitioner to show that “the 4
violation affected substantial rights and that there is a 5
reasonable probability that, but for the error, he would not have 6
entered the plea.” United States v. Vaval, 404 F.3d 144, 151 (2d 7
Cir. 2005) (internal quotation marks and citation omitted). 8
Given this legal background, the principal issue in the 9
present matter is whether the statements that Zhang was subject 10
to “possible post sentence deportation,” Plea Tr. at 14, that his 11
conviction “could result” in deportation, id. at 15, and that he 12
“may be deported,” Sentencing Tr. at 410, were, in fact, 13
accurate. If the statements were accurate at the time they were 14
made, then they could not reasonably be said to be misleading and 15
could not have rendered Zhang’s guilty plea involuntary. 16
The district court assumed that Zhang’s conviction was for 17
an aggravated felony subjecting him to automatic deportation, 18
noting that it was “undisputed in this case that Zhang’s mail 19
fraud conviction constitutes an aggravated felony under the 20
statute.” Zhang I, 401 F.Supp.2d at 241. As a result, the 21
district court's analysis focused on whether Zhang could 22
realistically apply for relief from automatic deportation, such 23
as asylum or protection under the CAT. Id. at 242. The district 24

-- 12 of 16 --

13
court determined that Zhang, as an aggravated felon, would be 1
“ineligible for discretionary relief from removal such as asylum, 2
8 U.S.C. § 1158(b)(2)(B)(I); restriction on removal, 8 U.S.C. § 3
1231(b)(3)(B); cancellation of removal, 8 U.S.C. § [1229b]; and 4
voluntary departure, 8 U.S.C. § [1229c].” Id. at 241. Likewise, 5
even if entitled to protection under CAT, an aggravated felon who 6
had been sentenced to at least 5 years’ imprisonment is entitled 7
only to have his removal deferred to a country where he is less 8
likely to be tortured. 8 C.F.R. § 208.17(a). Under such 9
circumstances, and assuming Zhang’s conviction was indisputably 10
for an aggravated felony, Judge Spatt found that “possible,” 11
“could,” and “may” were misleading, given that Zhang’s 12
deportation was virtually certain. Zhang I, 401 F.Supp.2d at 13
242. 14
At the time the allegedly misleading statements were made, 15
however, it was far from clear that Zhang’s conviction would 16
ultimately constitute an aggravated felony. Indeed, the question 17
of whether Zhang pled guilty to an aggravated felony is still in 18
dispute. For deportation purposes, the term “aggravated felony” 19
is defined, in relevant part, as “an offense that involves fraud 20
or deceit in which the loss to the victim or victims exceeds 21
$10,000.” 8 U.S.C. § 1101(a)(43)(M)(i). Thus, mail fraud does 22
not constitute an aggravated felony unless the loss exceeds 23
$10,000. Zhang pled guilty to Count One of the superseding 24

-- 13 of 16 --

14
indictment -- a single count of mail fraud involving the sale of 1
DNP to an individual in New York who was not James Shull or Eric 2
Perrin. At the time of the plea proceeding, it was not known 3
with certainty whether the loss amount for the single count to 4
which Zhang was pleading guilty would exceed $10,000. While the 5
plea agreement contained a loss estimate of $70,000 to $120,000, 6
Zhang explicitly reserved the right to challenge the loss 7
calculation at sentencing, and the parties struck the line in the 8
plea agreement stating that “[t]he defendant agrees with this 9
guidelines calculation.” Indeed, Zhang -- in pressing his claim 10
of ineffective assistance of counsel -- argues in his brief 11
before this court that the count to which he pled guilty did not 12
involve a loss of $10,000, and that his “[c]ounsel could have 13
easily insured that [Zhang] would not face deportation by 14
specifying the exact amount of money that was involved in the 15
single transaction for which [Zhang] pleaded guilty . . . .” Br. 16
for Petitioner-Appellee at 25. Thus, at the time of the plea 17
proceeding, neither the court nor the government could know that 18
Zhang’s conviction would qualify as an aggravated felony, 19
subjecting him to “automatic” deportation.1 In such 20
circumstances, the statement that Zhang faced “possible” 21
deportation was, in fact, completely accurate. 22
The statements thus served to put Zhang on notice that his 23
guilty plea had potential immigration consequences, and provided 24

-- 14 of 16 --

15
an opportunity to pursue those consequences more fully with his 1
attorney or with an immigration specialist. That is all that is 2
required. To be sure, the statements were not a full elaboration 3
of the immigration consequences of a guilty plea, but they were 4
not misleading or prejudicial in any way. To hold a sentencing 5
court that has decided to address the topic to a higher standard 6
of detail in explaining possible immigration ramifications -- a 7
notoriously complex and constantly shifting area of law -- would 8
likely have the perverse effect of encouraging sentencing courts 9
simply to avoid the issue entirely, lest a reviewing court find a 10
statement to be, in retrospect, misleading. That Zhang’s counsel 11
allegedly failed to apprise Zhang more fully of the immigration 12
consequences of his plea, and allegedly failed to take actions 13
which would have shielded Zhang from mandatory deportation, 14
serves as the basis for Zhang’s claim of ineffective assistance 15
of counsel, which we now remand to the district court for 16
consideration. 17
CONCLUSION 18
For the foregoing reasons, we vacate the order of the 19
district court and remand for further consideration consistent 20
with this opinion. 21

-- 15 of 16 --

16
1. Zhang suggests that the government’s contention that he was
not convicted of an aggravated felony contradicts the
government’s position below, where it assumed that Zhang’s
conviction constituted an aggravated felony. As noted, however,
Zhang himself seeks to preserve the claim that the count to which
he pled guilty did not constitute an aggravated felony at the
time of the plea colloquy and that it was only the incompetence
of his attorney that prevented the record from clearly showing
that his crime was not an aggravated felony.
FOOTNOTES 1
2

-- 16 of 16 --