Farhane v. United States

Docket Number20-1666,August Term 2021
Decision Date11 August 2023
PartiesAbderrahmane FARHANE, Petitioner-Appellant, v. UNITED STATES of America, Respondent-Appellee
CourtU.S. Court of Appeals — Second Circuit

Appeal from the United States District Court for the Southern District of New York.(Loretta A. Preska, J.)

Ramzi Kassem (Naz Ahmad, Princess Masilungan, Mudassar Toppa, on the brief), CLEAR Clinic, Main Street Legal Services, Inc., CUNY School of Law, Long Island City, NY; Alan E. Schoenfeld, Margaret T. Artz, Paloma Naderi, on the brief, Wilmer Cutler Pickering Hale and Dorr LLP, New York, NY, for Petitioner-Appellant Abderrahmane Farhane.

Jun Xiang (Karl Metzner, on the brief), Assistant United States Attorneys, for Audrey Strauss, United States Attorney for the Southern District of New York, New York, NY, for Respondent-Appellee United States of America.

Joel B. Rudin, Matthew A. Wasserman, Haran Tae, on the brief, National Association of Criminal Defense Lawyers, New York, NY, and Law Offices of Joel B. Rudin, P.C., New York, NY; Timothy P. Murphy, on the brief, New York State Association of Criminal Defense Lawyers, Albany, NY, for amici curiae National Association of Criminal Defense Lawyers and New York State Association of Criminal Defense Lawyers.

Andrew Z. Michaelson, Ana V.B. Daily, Kathryn R. Barry, on the brief, King & Spalding LLP, New York, NY; John C. Yang, Niyati Shah, Marita Etcubañez, on the brief, Asian Americans Advancing Justice, Washington, DC, for amicus curiae Asian Americans Advancing Justice.

Andrew D. Silverman, Daniel A. Rubens, Alyssa Barnard-Yanni, Lauren Weber, on the brief, Orrick, Herrington & Sutcliffe LLP, New York, NY, Seattle, WA, Washington, DC, for amici curiae Professors of Criminal Law, Criminal Procedure, Immigration Law, and Legal Ethics.

Manuel D. Vargas, Marie Mark, Nabilah Siddiquee, Leila Kang, on the brief, Immigrant Defense Project, New York, NY, for amicus curiae Immigrant Defense Project.

Before: Walker, Wesley, and Carney, Circuit Judges.

Judge Walker writes for the majority and concurs in a separate opinion.

Judge Carney dissents in a separate opinion.

John M. Walker, Jr., Circuit Judge:

Abderrahmane Farhane appeals from the denial in the United States District Court for the Southern District of New York (Loretta A. Preska, J.) of his habeas petition to vacate his 2006 guilty plea, conviction, and sentence. Farhane asserts that he received ineffective assistance of counsel because his lawyer did not warn him of the risks of denaturalization and possible subsequent deportation arising from his guilty plea. For the reasons that follow, we AFFIRM the district court.

BACKGROUND

In 2006, Appellant Farhane, a naturalized American citizen born in Morocco, pleaded guilty to providing false statements to federal law enforcement and conspiring to violate a money laundering statute, 18 U.S.C. § 1956. In his allocution, he stated that, in 2001, he conspired to transfer money to mujahideen in Afghanistan and Chechnya. He was sentenced in the Southern District of New York to 156 months of imprisonment and two years of supervised release. In 2011, after a lengthy appeal process, his conviction became final.

In 2017, Farhane was released from custody and returned to his home in Brooklyn. In August 2018, the government filed a complaint in the Eastern District of New York seeking to revoke Farhane's citizenship under 8 U.S.C. § 1451(a). Section 1451(a) provides for the civil denaturalization of individuals whose naturalization orders and certificates were "illegally procured or were procured by concealment of a material fact or by willful misrepresentation."1

Farhane had been naturalized in 2002. During that process, he told the government, on two forms and in one interview under oath, that he had never knowingly committed a crime for which he had not been arrested. This was a lie. In fact, just a few months earlier, Farhane had conspired with two others (one of whom was an FBI informant) to send money to fighters engaged in jihad in Afghanistan and Chechnya. They discussed the topic multiple times in person and over the phone, and Farhane gave advice as to how to avoid law enforcement detection of the money transfer. Relying on Farhane's 2006 guilty plea to these crimes, the denaturalization complaint alleged that Farhane had been unlawfully naturalized because he had: (a) joined a money laundering conspiracy and (b) concealed it from naturalization authorities.

In December 2018, while still on supervised release after serving his prison sentence, Farhane filed a 28 U.S.C. § 2255 habeas corpus petition in the Southern District of New York to vacate his guilty plea, conviction, and sentence. He asserted that he had received ineffective assistance of counsel at the time of his 2006 guilty plea because his lawyer had not warned him of the risk of denaturalization and deportation before he pleaded guilty.2 The district court denied the petition, concluding that his counsel's failure to warn him of the denaturalization risk was not objectively unreasonable. We granted Farhane's motion for a certificate of appealability. The denaturalization proceeding in the Eastern District has been stayed pending the resolution of Farhane's habeas petition.

DISCUSSION

On appeal, Farhane claims that he received ineffective assistance of counsel when his lawyer failed to tell him that denaturalization and deportation could be consequences of his pleading guilty. The Supreme Court set forth the test for ineffective assistance in Strickland v. Washington, requiring a defendant to establish both his trial counsel's deficient performance and the defendant's resulting prejudice.3 Farhane argues that the Sixth Amendment required his lawyer to warn him of the possible naturalization and immigration consequences of his guilty plea. Farhane says that, if he had known of these risks, he would not have pleaded guilty.

The government responds by arguing, as a threshold matter, that the Sixth Amendment does not require attorneys to warn of the risk of denaturalization. It also asserts that Farhane cannot establish either element of the Strickland test.4 Because civil denaturalization is a collateral and not a direct consequence of a conviction, we agree that the Sixth Amendment does not require attorneys to warn of that risk. Thus, we affirm the district court.

I. The Sixth Amendment and Denaturalization

The Sixth Amendment guarantees criminal defendants the effective assistance of counsel during plea negotiations.5 Effective assistance includes warning defendants of the "direct" consequences of pleading guilty, such as the offense's maximum prison term and the likely sentence as set forth in a plea agreement.6 We have long held, however, that an attorney need not warn of every possible "collateral consequence of conviction."7 Such collateral consequences are "categorically removed from the scope of the Sixth Amendment."8 A defendant can only establish an ineffective assistance claim as to a collateral consequence if his attorney affirmatively misadvises him.9 Failing to warn of the collateral risk alone is not enough.

The instant appeal is resolved by the straightforward application of this direct/collateral framework. Farhane and the dissent suggest, however, that this framework may not survive the Supreme Court's decision in Padilla v. Kentucky.10 Accordingly, we take this opportunity to reaffirm the direct/collateral distinction and apply it in the post-Padilla context. In doing so, we hold that the distinction remains valid, that it applies to civil denaturalization, and that such denaturalization is a collateral consequence of conviction and so is not covered by the Sixth Amendment's right to effective assistance of counsel.

A. The Direct/Collateral Framework

The distinction between direct consequences, as to which a constitutionally competent attorney must advise her client before he enters a guilty plea, and collateral consequences, about which she need not, is grounded in the text of the Sixth Amendment. The amendment guarantees a defendant "the [a]ssistance of [c]ounsel for his defen[s]e" in his "criminal prosecution[]."11 The amendment's scope is thus textually limited to the direct consequences of the prosecution and does not require "sound advice about the collateral consequences of conviction."12

This language accords with the practical limitations of law practice. Criminal lawyers are "not expected to possess—and very often do not possess—expertise in other areas of the law, and it is unrealistic to expect them to provide expert advice on matters that lie outside their area of training and experience."13 Indeed, a conviction's potential collateral consequences are numerous and varied. They include "civil commitment, civil forfeiture, the loss of the right to vote, disqualification from public benefits, ineligibility to possess firearms, dishonorable discharge from the Armed Forces, and loss of business or professional licenses."14 Some limiting principle is thus required. Otherwise, as Farhane is attempting to do here, guilty pleas could be overturned years or decades later due to events that a competent defense counsel could not have reasonably foreseen.

It is unsurprising, then, that courts have nearly uniformly applied the direct/collateral framework in the Sixth Amendment context. In Hill v. Lockhart, the Supreme Court explicitly avoided the question of whether the Sixth Amendment applies to the collateral consequences of a guilty plea.15 Since then, at least ten circuit courts and thirty state appellate courts have held that "counsel's failure to inform a defendant of the collateral consequences of a guilty plea is never a violation of the Sixth Amendment," with only a handful of state courts concluding otherwise.16 Indeed, the framework is so uniformly applied that, despite lacking explicit Supreme Court sanction, it has been described as "one of the...

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