05-6662-pr
     Zhang v. United States


 1                                 UNITED STATES COURT OF APPEALS
 2
 3                                     FOR THE SECOND CIRCUIT
 4
 5                                       August Term, 2006
 6
 7   (Argued: January 11, 2007                        Decided: October 23, 2007)
 8
 9                         Docket No. 05-6662-pr
10   - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -
11
12   SEAN ZHANG,
13
14                 Petitioner-Appellee,
15
16                            v.
17
18   UNITED STATES OF AMERICA,
19
20                 Respondent-Appellant.
21
22   - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -
23
24   B e f o r e:             WINTER, CABRANES, Circuit Judges, and KORMAN,
25                            District Judge.*
26
27          Appeal from an order of the United States District Court for

28   the Eastern District of New York (Arthur D. Spatt, Judge)

29   granting a petition for habeas corpus relief under 28 U.S.C. §

30   2255.      Petitioner-appellee, a legal permanent resident of the

31   United States, pled guilty to one count of mail fraud under 18

32   U.S.C. § 1341.           The district court found that statements of the

33   magistrate judge and prosecutor about the immigration

34   consequences of the conviction affirmatively misled the

            *
          The Honorable Edward R. Korman, of the United States
     District Court for the Eastern District of New York, sitting by
     designation.

                                                 1
 1   petitioner-appellee, thus rendering his guilty plea involuntary.

 2   We find that the statements of the magistrate judge and

 3   prosecutor -- while not full explanations -- were not

 4   sufficiently misleading to render the guilty plea involuntary.

 5   Accordingly, we vacate and remand for consideration of

 6   petitioner-appellee’s other constitutional arguments.

 7                                   GARY SCHOER, Syosset, New York, for
 8                                   Petitioner-Appellee.
 9
10                                   CARRIE CAPWELL, Assistant United
11                                   States Attorney (Roslynn R.
12                                   Mauskopf, United States Attorney
13                                   for the Eastern District of New
14                                   York, on the brief, and Peter A.
15                                   Norling, Assistant United States
16                                   Attorney, of counsel), United
17                                   States Attorney’s Office for the
18                                   Eastern District of New York,
19                                   Brooklyn, New York, for Respondent-
20                                   Appellant.
21
22   WINTER, Circuit Judge:

23        The government appeals Judge Spatt’s order granting Sean

24   Zhang’s 28 U.S.C. § 2255 petition for habeas corpus and vacating

25   his plea of guilty to mail fraud and resultant sentence of 60

26   months’ imprisonment.    Judge Spatt found that Zhang’s guilty plea

27   was involuntary because the magistrate judge and the prosecutor

28   had affirmatively misled Zhang during the plea colloquy with

29   respect to the likelihood of his being deported as a result of

30   his conviction.   Zhang v. United States, 

, 243-

31   44 (E.D.N.Y. 2005) (“Zhang I”).       On appeal, the government

32   principally argues that the representations of the magistrate

                                       2
 1   judge and prosecutor -- that Zhang faced possible, rather than

 2   certain, deportation -- were not affirmatively misleading or

 3   prejudicial, and that the court had no greater obligation to

 4   spell out the possible collateral effects of Zhang’s guilty plea.

 5        We conclude that the statements made during the colloquy

 6   were not affirmatively misleading, and that they did not render

 7   Zhang’s guilty plea involuntary.       We therefore vacate the order

 8   below.   Zhang has also raised a claim of ineffective assistance

 9   of counsel, which we remand to the district court for further

10   proceedings.

11                               BACKGROUND

12        Sean Zhang came to the United States from China in 1985, at

13   the age of seven.   Zhang 

.      Zhang’s family

14   was granted asylum on the basis of his father’s public criticism

15   of Communism and the Chinese government.       

16   Cornell University and graduated with a Bachelor of Science

17   degree in “Food Science.”   

has spent the bulk

18   of his life in the United States, does not speak Chinese

19   proficiently, is married to an American citizen, and has long

20   been a legal permanent resident, he has never become an American

21   citizen.   

2001, while working as a chemist, Zhang began mixing and

23   selling capsules of the chemical 2,4 Dinitrophenol (“DNP”).           

addition to its many industrial and research uses, DNP, when


                                        3
 1   ingested by humans, acts as a metabolic stimulant and can reduce

 2   body fat.   

the effect of DNP, the drug is banned

 3   for human use by the Food and Drug Administration.      

DNP is sometimes used by bodybuilders seeking to

 5   quickly reduce their body fat.    

screen name “DNP

 6   Guru,” Zhang used a bodybuilding website to promote and sell DNP.

 7   

Zhang’s customers, Eric Perrin, died as a result of

 8   ingesting DNP purchased from Zhang.     

James

 9   Shull, lapsed into a 10-day coma caused by DNP prepared and sold

10   by Zhang.   

was indicted on ten counts of introducing a misbranded

12   drug into interstate commerce, in violation of 21 U.S.C. §

13   331(a), and ten counts of mail fraud, in violation of 18 U.S.C. §

14   1341.   Zhang entered into a plea agreement in which he agreed to

15   plead guilty to a single count of mail fraud with a maximum

16   penalty of 60 months and waive his right to appeal if sentenced

17   to 60 months or less.    The plea agreement stated that the

18   government would seek an upward departure based upon Perrin’s

19   death and Shull’s injuries, and included the statement, “Other

20   penalties: Removal.”    The plea agreement also contained the

21   government’s loss estimate of between $70,000 and $120,000.

22         According to Zhang, in discussing a guilty plea, his

23   attorney told him that any resulting deportation proceeding would

24   be discretionary, and that deportation was unlikely given his


                                       4
 1   personal history and family circumstances.        On June 25, 2002,

 2   Zhang entered his guilty plea before a magistrate judge.        During

 3   the plea allocution, the prosecutor stated that Zhang “agrees he

 4   [is] subject to possible post sentence deportation.”        Plea Tr. at

 5   14.   The magistrate judge further stated that “it’s not indicated

 6   as a consequence of your plea and the plea agreement but the

 7   government indicated that this felony conviction because of your

 8   immigration status could result in your deportation.        Do you

 9   understand that?”   Zhang answered “Yes, I understand.”       

  15.   Elsewhere in the allocution, the prosecutor noted that

11   Zhang’s counsel had reserved the right to move for a downward

12   departure, and to challenge any loss calculation.

13         A year later, following a hearing pursuant to United States

14   v. Fatico, 

(2d Cir. 1978), Zhang was sentenced to 60

15   months’ imprisonment plus three years’ supervised release, and

16   ordered to pay $113,414.53 in restitution.        At the sentencing

17   hearing, the prosecutor noted that “there is another condition of

18   supervised release.   He may be deported.       If he does, if you can

19   put on the judgment that he should not reenter without the

20   permission of the Attorney General.”        Sentencing Tr. at 410.    The

21   sentencing judge agreed, and stated that “if the defendant is

22   deported, he’s not to reenter the United States illegally without

23   the consent of the government.”       

to his plea agreement, Zhang did not appeal his


                                       5
 1   conviction or sentence.    After the time for filing a direct

 2   appeal had passed, Zhang received a Notice to Appear from the

 3   Bureau of Immigration and Customs Enforcement (“ICE”).    Zhang

 4   claims at this time that he first became aware that he faced

 5   mandatory deportation as a result of having been convicted of an

 6   “aggravated felony” -- defined in relevant part for deportation

 7   purposes as “an offense that involves fraud or deceit in which

 8   the loss to the victim or victims exceeds $10,000.”    8 U.S.C. §

 9   1101(a)(43)(M)(i).   On June 17, 2004, Zhang filed a habeas corpus

10   petition in the district court pursuant to 28 U.S.C. § 2255,

11   seeking to vacate his conviction on two grounds:    (i) that the

12   statements of the prosecutor and the court regarding possible

13   deportation were affirmatively misleading and violated Fed. R.

14   Crim. P. 11; and (ii) that he received ineffective assistance of

15   counsel regarding deportation.    Zhang 

.

16   The government argued that the statements during the course of

17   sentencing were accurate because Zhang could potentially avoid

18   deportation by applying for asylum or relief under the Convention

19   Against Torture (“CAT”).

20        On July 29, 2005, the district court held a hearing on

21   whether Zhang’s guilty plea was involuntary because of the

22   characterization of the chances of deportation as less than

23   certain.    Consideration of the ineffective assistance claim was

24   deferred.


                                       6
 1        On November 18, 2005, the district court issued its decision

 2   vacating Zhang’s conviction.     Zhang I, 

.   The

 3   court first held that Zhang’s claim was not procedurally barred

 4   by his failure to raise it on direct appeal or by his plea

 5   agreement’s waiver of collateral attack.     

  The court

 6   then found that while Second Circuit law does not require a judge

 7   to alert a defendant to the immigration consequences of a guilty

 8   plea, affirmative misinformation about those consequences can

 9   render a plea involuntary under Rule 11.     

10   Finally, the district court determined that it was, in fact,

11   materially misleading to inform Zhang that deportation was

12   “merely possible, not probably or certain,” and that “the

13   misrepresentation was sufficient to render Zhang’s plea

14   constitutionally involuntary.”    

15        The government appealed.

16                                DISCUSSION

17        In appeals under 28 U.S.C. § 2255, “this Court reviews

18   factual findings for clear error and questions of law de novo.”

19   Harris v. United States, 

, 79 (2d Cir. 2004) (internal

20   quotation marks omitted).

21        As a threshold issue, the government argues that Zhang

22   procedurally defaulted by failing to bring his claims on direct

23   appeal.    “A motion under § 2255 is not a substitute for an

24   appeal.”   United States v. Munoz, 

, 637 (2d Cir.


                                        7
 1   1998).    In general, a claim may not be presented in a habeas

 2   petition where the petitioner failed to properly raise the claim

 3   on direct review.    Reed v. Farley, 

, 354 (1994).     The

 4   rule does not generally apply to claims of ineffective assistance

 5   of counsel.    Massaro v. United States, 

, 505-06

 6   (2003).    The claim ruled on in the district court and before us

 7   now, however, is not Zhang’s ineffective assistance of counsel

 8   claim, but rather the claim that Zhang’s guilty plea was

 9   involuntary.    If such a claim has not been presented on direct

10   review, the procedural default bar may be overcome only where the

11   petitioner establishes either (1) “cause” for the failure to

12   bring a direct appeal and “actual prejudice” from the alleged

13   violations; or (2) “actual innocence.”    Bousley v. United States,

14   

, 622 (1998).    “To satisfy the ‘cause’ requirement,

15   the petitioner must show circumstances ‘external to the

16   petitioner, something that cannot be fairly attributed to him.’”

17   Rosario-Dominguez v. United States, 

, 508

18   (S.D.N.Y. 2005) (quoting Marone v. United States, 

, 67

19   (2d Cir. 1993) and Coleman v. Thompson, 

, 753

20   (1991)).

21        Zhang argues that because of the (mis)representations by the

22   court, his counsel, and the government about the deportation

23   consequences of his plea, he was unaware of those consequences

24   until he received a letter from the ICE, and that this serves as


                                       8
 1   “cause” justifying his failure to bring the claim on direct

 2   appeal.    However, we cannot determine whether the allegedly

 3   misleading statements prejudiced Zhang and excuse his failure to

 4   bring his claims on direct appeal without first determining

 5   whether they were, in fact, affirmatively misleading.      If the

 6   statements were affirmatively misleading and prejudicial,

 7   procedural default would be waived and Zhang would prevail on the

 8   merits.    If the statements were not affirmatively misleading and

 9   prejudicial, procedural default would not be waived, and Zhang

10   would lose on the merits.    Either way, we must address the

11   merits.

12        Prior to accepting a guilty plea, a court must advise the

13   defendant of his right to plead not guilty and of the rights

14   waived by pleading guilty.    Fed. R. Crim. P. 11(b)(1).    Rule 11

15   also requires a court to tell the defendant of the possible

16   direct consequences of a guilty plea, such as the maximum prison

17   term, the maximum fine, and the effect of possible supervised

18   release.    

need not, however, inform a defendant

19   about the “collateral” consequences of a guilty plea.      See Michel

20   v. United States, 

, 465 (2d Cir. 1974); Bye v. United

21   States, 

, 179 (2d Cir. 1970) (“[A]n accused need not

22   be informed prior to the acceptance of his guilty plea about

23   every conceivable collateral effect the conviction entered on the

24   plea might have.”).


                                        9
 1        The possibility of discretionary deportation after a guilty

 2   plea is a “collateral” consequence that need not be addressed at

 3   the plea hearing.   

.      The passage of

 4   the Illegal Immigration Reform and Immigrant Responsibility Act

 5   of 1996 (“IIRIRA”) and the Antiterrorism and Effective Death

 6   Penalty Act of 1996 (“AEDPA”), however, has altered the landscape

 7   of immigration law, and deportation of aggravated felons is now

 8   automatic and non-discretionary.       8 U.S.C. § 1227(a)(2)(A)(iii);

 9   see also INS v. St. Cyr, 

, 325 (2001) (referring to

10   deportation of aggravated felons as “certain”).      Nonetheless,

11   several circuits have held that “automatic” deportation under

12   IIRIRA is still a collateral consequence that need not be

13   addressed prior to a court’s accepting a guilty plea.       See El-

14   Nobani v. United States, 

, 421 (6th Cir. 2002) (“[I]t

15   is clear that deportation is not within the control and

16   responsibility of the district court, and hence, deportation is

17   collateral to a conviction.”); United States v. Amador-Leal, 276

, 516-17 (9th Cir. 2002) (“[W]hether an alien will be

19   removed is still up to the INS.    There is a process to go

20   through, and it is wholly independent of the court imposing

21   sentence . . . . Removal is not part of the sentence.”); and

22   United States v. Gonzalez, 

, 27 (1st Cir. 2000)

23   (“However ‘automatically’ [the defendant’s] deportation . . .

24   might follow from his conviction, it remains beyond the control


                                       10
 1   and responsibility of the district court in which that conviction

 2   was entered and it thus remains a collateral consequence

 3   thereof.”).

 4        Although we have acknowledged the existence of the issue,

 5   United States v. Cuoto, 

, 190 (2d Cir. 2002), we have

 6   not decided whether “automatic” deportation is a collateral

 7   consequence of a guilty plea that need not be mentioned or a

 8   direct consequence that required discussion during the plea

 9   proceeding.   Once again, the issue is not before us.   As the

10   district court noted, “[w]hether automatic deportation is a

11   direct or collateral consequence is of no matter in this case

12   because the court did address deportation at the plea hearing.”

13   Zhang 

.   We agree.

14        “Rule 11 sets forth requirements for a plea allocution and

15   is designed to ensure that a defendant’s plea of guilty is a

16   voluntary and intelligent choice among the alternative courses of

17   action open to the defendant.”   United States v. Andrades, 169

, 133 (2d Cir. 1999) (internal quotation marks and

19   citation omitted).   To successfully challenge a guilty plea

20   conviction based on a Rule 11 violation, a petitioner must

21   establish that the violation constituted a “constitutional or

22   jurisdictional” error, or establish that the error resulted in a

23   “complete miscarriage of justice,” or in a proceeding

24   “inconsistent with the rudimentary demands of fair procedure.”


                                      11
 1   United States v. Timmreck, 

, 783 (1979) (internal

 2   quotation marks omitted).   In addition, the petitioner must

 3   demonstrate that the violation was prejudicial -- where the error

 4   was not preserved, this requires the petitioner to show that “the

 5   violation affected substantial rights and that there is a

 6   reasonable probability that, but for the error, he would not have

 7   entered the plea.”   United States v. Vaval, 

, 151 (2d

 8   Cir. 2005) (internal quotation marks and citation omitted).

 9        Given this legal background, the principal issue in the

10   present matter is whether the statements that Zhang was subject

11   to “possible post sentence deportation,” Plea Tr. at 14, that his

12   conviction “could result” in deportation, 

and that he

13   “may be deported,” Sentencing Tr. at 410, were, in fact,

14   accurate.   If the statements were accurate at the time they were

15   made, then they could not reasonably be said to be misleading and

16   could not have rendered Zhang’s guilty plea involuntary.

17        The district court assumed that Zhang’s conviction was for

18   an aggravated felony subjecting him to automatic deportation,

19   noting that it was “undisputed in this case that Zhang’s mail

20   fraud conviction constitutes an aggravated felony under the

21   statute.”   Zhang 

.   As a result, the

22   district court's analysis focused on whether Zhang could

23   realistically apply for relief from automatic deportation, such

24   as asylum or protection under the CAT.   

  The district


                                     12
 1   court determined that Zhang, as an aggravated felon, would be

 2   “ineligible for discretionary relief from removal such as asylum,

 3   8 U.S.C. § 1158(b)(2)(B)(I); restriction on removal, 8 U.S.C. §

 4   1231(b)(3)(B); cancellation of removal, 8 U.S.C. § [1229b]; and

 5   voluntary departure, 8 U.S.C. § [1229c].”     

  Likewise,

 6   even if entitled to protection under CAT, an aggravated felon who

 7   had been sentenced to at least 5 years’ imprisonment is entitled

 8   only to have his removal deferred to a country where he is less

 9   likely to be tortured.    8 C.F.R. § 208.17(a).   Under such

10   circumstances, and assuming Zhang’s conviction was indisputably

11   for an aggravated felony, Judge Spatt found that “possible,”

12   “could,” and “may” were misleading, given that Zhang’s

13   deportation was virtually certain.    Zhang 

  242.

15          At the time the allegedly misleading statements were made,

16   however, it was far from clear that Zhang’s conviction would

17   ultimately constitute an aggravated felony.    Indeed, the question

18   of whether Zhang pled guilty to an aggravated felony is still in

19   dispute.    For deportation purposes, the term “aggravated felony”

20   is defined, in relevant part, as “an offense that involves fraud

21   or deceit in which the loss to the victim or victims exceeds

22   $10,000.”    8 U.S.C. § 1101(a)(43)(M)(i).   Thus, mail fraud does

23   not constitute an aggravated felony unless the loss exceeds

24   $10,000.    Zhang pled guilty to Count One of the superseding


                                      13
 1   indictment -- a single count of mail fraud involving the sale of

 2   DNP to an individual in New York who was not James Shull or Eric

 3   Perrin.   At the time of the plea proceeding, it was not known

 4   with certainty whether the loss amount for the single count to

 5   which Zhang was pleading guilty would exceed $10,000.   While the

 6   plea agreement contained a loss estimate of $70,000 to $120,000,

 7   Zhang explicitly reserved the right to challenge the loss

 8   calculation at sentencing, and the parties struck the line in the

 9   plea agreement stating that “[t]he defendant agrees with this

10   guidelines calculation.”   Indeed, Zhang -- in pressing his claim

11   of ineffective assistance of counsel -- argues in his brief

12   before this court that the count to which he pled guilty did not

13   involve a loss of $10,000, and that his “[c]ounsel could have

14   easily insured that [Zhang] would not face deportation by

15   specifying the exact amount of money that was involved in the

16   single transaction for which [Zhang] pleaded guilty . . . .”     Br.

17   for Petitioner-Appellee at 25.   Thus, at the time of the plea

18   proceeding, neither the court nor the government could know that

19   Zhang’s conviction would qualify as an aggravated felony,

20   subjecting him to “automatic” deportation.1   In such

21   circumstances, the statement that Zhang faced “possible”

22   deportation was, in fact, completely accurate.

23        The statements thus served to put Zhang on notice that his

24   guilty plea had potential immigration consequences, and provided


                                      14
 1   an opportunity to pursue those consequences more fully with his

 2   attorney or with an immigration specialist.   That is all that is

 3   required.   To be sure, the statements were not a full elaboration

 4   of the immigration consequences of a guilty plea, but they were

 5   not misleading or prejudicial in any way.   To hold a sentencing

 6   court that has decided to address the topic to a higher standard

 7   of detail in explaining possible immigration ramifications -- a

 8   notoriously complex and constantly shifting area of law -- would

 9   likely have the perverse effect of encouraging sentencing courts

10   simply to avoid the issue entirely, lest a reviewing court find a

11   statement to be, in retrospect, misleading.   That Zhang’s counsel

12   allegedly failed to apprise Zhang more fully of the immigration

13   consequences of his plea, and allegedly failed to take actions

14   which would have shielded Zhang from mandatory deportation,

15   serves as the basis for Zhang’s claim of ineffective assistance

16   of counsel, which we now remand to the district court for

17   consideration.

18                                  CONCLUSION

19        For the foregoing reasons, we vacate the order of the

20   district court and remand for further consideration consistent

21   with this opinion.




                                     15
1                                 FOOTNOTES

2

    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.




                                    16