United States of America v. Karnail Singh

RECOMMENDED FOR PUBLICATION
Pursuant to Sixth Circuit I.O.P. 32.1(b)
File Name: 26a0130p.06
UNITED STATES COURT OF APPEALS
FOR THE SIXTH CIRCUIT
UNITED STATES OF AMERICA,
Plaintiff-Appellee,
v.
KARNAIL SINGH,
Defendant-Appellant.
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No. 25-1523
Appeal from the United States District Court for the Eastern District of Michigan at Detroit.
No. 2:13-cr-20551-1—David M. Lawson, District Judge.
Decided and Filed: May 5, 2026
Before: GRIFFIN, THAPAR, and NALBANDIAN, Circuit Judges.
_________________
COUNSEL
ON BRIEF: Firooz T. Namei, MCKINNEY & NAMEI CO., L.P.A., Cincinnati, Ohio, for
Appellant. Jessica V. Currie, UNITED STATES ATTORNEY’S OFFICE, Detroit, Michigan,
for Appellee.
THAPAR, J., delivered the opinion of the court in which NALBANDIAN, J., joined, and
GRIFFIN, J., joined in the judgment. GRIFFIN, J. (pp. 11–12), delivered a separate concurring
opinion concurring in the judgment only.
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OPINION
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THAPAR, Circuit Judge. Karnail Singh, a naturalized U.S. citizen, pled guilty to using a
passport that he fraudulently obtained. He now seeks to set aside that conviction, claiming he
received ineffective assistance of counsel. Singh argues that his attorney should have explained
>

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that his guilty plea could lead to denaturalization. But the Sixth Amendment doesn’t require
attorneys to advise naturalized citizens that a guilty plea may carry the risk of denaturalization
and eventual deportation. So we affirm.
I.
Karnail Singh, a native of India, illegally entered the United States decades ago and then
applied for asylum. The government denied that application and ordered him deported. But that
didn’t deter Singh. Instead of leaving the country, he submitted another asylum application
listing a different name, birth date, place of birth, and parents. None of this new information was
true.
Singh then married an American citizen and applied for permanent-resident status, using
the same false information listed on his second asylum application. On that residency
application, Singh claimed that he had never been denied an immigration benefit and had never
provided false information on an immigration form before. Of course, neither statement was
true. But based on these misrepresentations, the government granted Singh permanent-resident
status. A few years later, Singh became a naturalized U.S. citizen.
As a new citizen, Singh obtained a U.S. passport. Following a trip abroad, he attempted
to reenter the United States using that passport. Officers at the border crossing asked Singh if he
had ever used any other names or birth dates. Singh replied that he hadn’t. But that, once again,
wasn’t true. So the government charged him with using a fraudulently obtained passport and
making a false statement to federal agents.
Singh eventually pled guilty to the fraudulent-passport charge, and the government
agreed to dismiss the false-statement charge. Singh’s plea agreement warned that his guilty plea
could “affect or even foreclose his eligibility to remain in this country.” R. 16, Pg. ID 43.
Nevertheless, Singh agreed that his decision to plead guilty was “wholly independent of the
immigration consequences.” Id. at 44. Then, at the plea hearing, the district court explained that
Singh’s guilty plea could “be used if the immigration services bring a petition to cancel [his]
citizenship.” R. 22, Pg. ID 127. Singh confirmed that he understood and proceeded to plead
guilty. The district court ultimately sentenced Singh to 12 months’ probation.

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A few years later, the government began proceedings to denaturalize Singh. The
government alleged that Singh illegally procured his citizenship because he wasn’t lawfully
admitted to the United States, committed fraud on his permanent-residency application, and
made willful misrepresentations on his naturalization application. It also alleged that Singh
lacked good moral character—and was thus ineligible for naturalization—because he made false
statements in his citizenship application and interview. The government argued that the factual
basis in Singh’s guilty plea “substantiates his concealment and use of two identities throughout
his immigration proceedings.” R. 30-4, Pg. ID 267–68. So the government claimed that Singh
couldn’t “reasonably dispute his deceptive actions.” Id. at 268.
Singh then petitioned for a writ of coram nobis before the district court. A coram nobis
petition is used to challenge the validity of a conviction or sentence when a habeas petition isn’t
available. Chaidez v. United States, 568 U.S. 342, 345 n.1 (2013). Singh claimed that his
conviction wasn’t valid because he received ineffective assistance of counsel. According to
Singh, his attorney incorrectly advised him that the plea agreement would “protect his
citizenship—unless he commit[ted] another crime.” R. 25, Pg. ID 148. The district court denied
the petition. We affirmed because Singh hadn’t established a reasonable probability that, but for
his counsel’s advice, he would have declined to plead guilty or negotiated a better deal. United
States v. Singh, 95 F.4th 1028, 1033–34 (6th Cir.), cert. denied, 145 S. Ct. 167 (2024) (mem.).
At that point, the case seemed to be over.
But a few months later, the Second Circuit, sitting en banc, decided Farhane v. United
States. 121 F.4th 353 (2d Cir. 2024) (en banc). Over multiple dissents, it held that the Sixth
Amendment requires defense attorneys to advise naturalized citizens of the risk of
denaturalization and eventual deportation following a guilty plea. Id. at 358. So Singh moved
for reconsideration of the district court’s denial. The district court denied that motion, and Singh
timely appealed.

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II.
This appeal presents a simple legal question: Does the Sixth Amendment require a
defense attorney to notify a naturalized citizen that a guilty plea may lead to denaturalization?1
Singh argues that our court should follow the Second Circuit’s decision in Farhane and conclude
that the answer is yes. But Farhane misapplied longstanding Supreme Court precedent. Simply
put, neither the Sixth Amendment nor Supreme Court precedent applying it requires attorneys to
advise naturalized citizens that a guilty plea may carry the risk of denaturalization and eventual
deportation.
A.
The Sixth Amendment guarantees criminal defendants’ right to the “effective assistance
of competent counsel.” Lafler v. Cooper, 566 U.S 156, 162 (2012). That right extends to the
plea-bargaining process. Id. This means a defense attorney must advise his client of the direct
consequences of any plea agreement, such as the maximum prison term that could be imposed.
Brady v. United States, 397 U.S. 742, 755 (1970); King v. Dutton, 17 F.3d 151, 154 (6th Cir.
1994). But a defense attorney isn’t constitutionally required to inform his client of any collateral
consequences stemming from the plea agreement. Chaidez, 568 U.S. at 350–51. A consequence
is collateral if it “remains beyond the control and responsibility of the district court in which
th[e] conviction was entered.” Saylor v. Nagy, No. 20-1834, 2021 WL 5356030, at *4 (6th Cir.
Nov. 17, 2021) (quoting El-Nobani v. United States, 287 F.3d 417, 421 (6th Cir. 2002)).
Examples include civil commitment, civil forfeiture, sex-offender registration, disqualification
from public benefits, loss of the right to vote, ineligibility to possess firearms, loss of
professional licenses, and discharge from the armed services. Chaidez, 568 U.S. at 349 n.5; see
also Padilla v. Kentucky, 559 U.S. 356, 376 (2010) (Alito, J., concurring in the judgment). In
1The concurrence thoughtfully argues that we shouldn’t address the Sixth Amendment issue because
Singh’s motion doesn’t meet the standard for reconsideration. Of course, we should avoid reaching constitutional
questions unless necessary. But here, Singh could be entitled to reconsideration if he identifies “a clear error of
law.” Gen. Motors, LLC v. FCA US, LLC, 44 F.4th 548, 563 (6th Cir. 2022). Singh urges us to agree with the
Second Circuit that “a straightforward application of” existing Supreme Court precedent requires defense attorneys
to tell their clients about the risk of denaturalization. Farhane, 121 F.4th at 363. If the Second Circuit were correct,
the district court’s failure to identify that rule would be a clear error of law that could entitle Singh to
reconsideration. So we must address the constitutional question to resolve this appeal.

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short, defense attorneys must tell their clients about direct—but not collateral—consequences of
a plea deal.
This distinction between direct and collateral consequences makes sense.
Start with the text of the Sixth Amendment. It guarantees an individual the right “to have
the Assistance of Counsel for his defence” in “all criminal prosecutions.” U.S. Const. amend.
VI. So the right to counsel is limited to assistance with the accused’s “defence” in a “criminal
prosecution[]” and doesn’t extend to advice about follow-on consequences or subsequent
proceedings.
The direct-collateral distinction also accounts for the practical limitations on lawyers’
skill and knowledge. Defense attorneys may know a lot about criminal law and procedure. But
they aren’t experts in other areas of the law. So it would be “unrealistic to expect them to
provide expert advice on matters that lie outside their area of training and experience.” Padilla,
559 U.S. at 376 (Alito, J., concurring in the judgment). Indeed, providing such advice
comes with significant risks. For example, the advice might be wrong and could lead to a
finding that the attorney was ineffective. Such a finding may then result in bar sanctions. See
Rodriguez-Penton v. United States, 905 F.3d 481, 490 (6th Cir. 2018) (Thapar, J., dissenting).
What’s more, clients may be worse off because they may forgo seeking advice from a real expert
in the field—in this case, an immigration lawyer.
For these reasons, state and lower federal courts “almost unanimously concluded” that
the Sixth Amendment doesn’t require an attorney to inform his client of a conviction’s collateral
consequences, making that “one of the most widely recognized rules of American law.”
Chaidez, 568 U.S. at 350–51 (quotation omitted).
The Supreme Court has created one notable exception to this rule. In Padilla
v. Kentucky, the Court “breach[ed] the previously chink-free wall between direct and collateral
consequences.” Chaidez, 568 U.S. at 352–53. It held that a defense attorney must inform an
alien that a guilty plea may carry a risk of deportation. Padilla, 559 U.S. at 359–60. That’s
because deportation is an especially “severe” consequence of a criminal conviction. Id. at 365.
Plus, our immigration laws have increasingly linked convictions with a risk of deportation. Id. at

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No. 25-1523 United States v. Singh Page 6
365–66. In fact, deportation has become a nearly automatic result for many aliens who are
convicted of crimes in this country. Id. at 366. That reality made it difficult for the Court to
classify deportation as either a direct or collateral consequence. Id. So it introduced a narrow
exception based on “the unique nature of deportation.” Id. at 365. But the Court “did not
eschew the direct-collateral divide across the board.” Chaidez, 568 U.S. at 355. Outside of the
deportation context, the direct-collateral divide continues to apply.
Applying that settled precedent to this case provides a straightforward answer: Singh’s
counsel wasn’t required to inform him of the risk of denaturalization. Civil denaturalization is a
separate proceeding that requires the government to file suit in the judicial district where the
naturalized citizen resides. See 8 U.S.C. § 1451(a). And that new suit is “beyond the control
and responsibility of the district court” in which the naturalized citizen was convicted. Saylor,
2021 WL 5356030, at *4 (quotation omitted). In this case, the conviction and denaturalization
proceedings occurred in entirely different judicial districts. Singh was convicted in the Eastern
District of Michigan, and the government sought denaturalization in the Eastern District of
Kentucky, where Singh resides. But even if all this litigation occurred in the same district,
denaturalization is still a new and separate civil proceeding unconnected to any prior criminal
“defence.” U.S. Const. amend. VI. So it’s a quintessential collateral consequence that falls
outside the Sixth Amendment’s scope.
B.
Still, Singh urges us to adopt a new exception to the direct-collateral divide and hold that
the Sixth Amendment requires defense attorneys to advise naturalized citizens of the risk of
denaturalization. Singh primarily hangs his hat on the Second Circuit’s recent decision in
Farhane. According to the Second Circuit, a “straightforward application of Padilla” requires
counsel to advise his client of the risk of denaturalization and eventual deportation. Farhane,
121 F.4th at 363. Not so.
The Second Circuit misread Padilla by extending its reasoning to denaturalization. For
starters, the Padilla Court took pains to limit its holding to advice about deportation, noting the
“unique nature” of that penalty. Padilla, 559 U.S. at 365–66; see also United States v. Reeves,

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695 F.3d 637, 640 (7th Cir. 2012) (“Padilla is rife with indications that the Supreme Court meant
to limit its scope to the context of deportation only.”). But the Second Circuit ignored those
limitations and overlooked critical distinctions between deportation and denaturalization.
It’s true that deportation and denaturalization share some similarities. Both are “severe”
consequences. Fedorenko v. United States, 449 U.S. 490, 505 (1981). Indeed, for many people
around the world, American citizenship is their “highest hope.” Schneiderman v. United States,
320 U.S. 118, 122 (1943). After all, “nowhere in the world today is the right of citizenship of
greater worth to an individual than it is in this country.” Id. So losing that immense privilege
can be “severe and unsettling.” Fedorenko, 449 U.S. at 505. But many effects of a guilty plea,
like losing the right to vote or being involuntarily committed to a mental institution, are also
severe. And we still consider those severe consequences to be collateral. Chaidez, 568 U.S. at
349 n.5. So the severity of a consequence doesn’t on its own implicate the Sixth Amendment.
Rather, the Padilla Court was concerned with both the severity of deportation and its
close connection with a criminal conviction. As Padilla explained, deportation for an alien is a
nearly automatic consequence of many criminal convictions. 559 U.S. at 366. But the same
isn’t true for denaturalization. That’s because the government retains significant discretion over
whether to institute separate denaturalization proceedings.2 See 8 U.S.C. § 1451(a). Exercising
that discretion, the government brought fewer than 150 denaturalization proceedings across the
country from 1968 until 2012. Amber Qureshi, The Denaturalization Consequences of Guilty
Pleas, 130 Yale L.J.F. 166, 170 (2020). In contrast, the government removed more than 68,000
aliens following a criminal conviction in 2024 alone. U.S. Immigr. & Customs Enf’t, Fiscal
Year 2024 Annual Report 32 (Dec. 19, 2024). These stark differences show just how rarely the
government seeks denaturalization compared to deportation. But even if it sought
denaturalization much more often, that wouldn’t change the result. Simply put, denaturalization
isn’t an automatic consequence of a criminal conviction in the same way that deportation is.
2Our analysis in this case is limited to civil denaturalization under section 1451(a). In contrast, section
1451(e) makes denaturalization “an automatic consequence of a criminal conviction under 18 U.S.C. § 1425.”
United States v. Maslenjak, 821 F.3d 675, 682 (6th Cir. 2016), vacated on other grounds by, 582 U.S. 335 (2017).
We express no view on whether the Sixth Amendment requires counsel to advise clients that pleading guilty to a
violation of section 1425 will lead to automatic denaturalization.

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What’s more, denaturalization doesn’t depend on whether the individual was convicted
of a crime. It depends on whether he procured citizenship illegally, through concealment,
or through willful misrepresentation. 8 U.S.C. § 1451(a). Citizenship is illegally procured if
an individual fails to comply with all the requirements for citizenship that Congress has
imposed—and many don’t mention conviction. Fedorenko, 449 U.S. at 506. These
requirements include being lawfully admitted to the United States, residing in the country for
five years, and having “good moral character.” 8 U.S.C. § 1427(a). An individual lacks good
moral character if, for example, he gives false testimony to secure an immigration benefit. Id.
§ 1101(f)(6). The immigration regulations also include a catch-all category for any individual
who “[c]ommitted unlawful acts that adversely reflect upon the applicant’s moral character.”
8 C.F.R. § 316.10(b)(3)(iii). These laws and regulations all have a common theme:
Denaturalization typically depends on the individual’s conduct leading up to or at the time of
denaturalization, regardless of whether the individual was ultimately convicted for that conduct.
So it’s not as closely connected to a conviction as deportation.
The denaturalization proceeding against Singh provides the perfect example. The
government alleged that he illegally procured naturalization because he engaged in fraud or
made willful misrepresentations and wasn’t lawfully admitted to the United States. It also
alleged that he lacked good moral character because he had committed unlawful acts by lying on
his naturalization form and because he gave false testimony under oath to immigration officials.
All these allegations depend on Singh’s conduct leading up to his naturalization. But notice
what’s missing: The government’s denaturalization complaint didn’t depend at all on whether
Singh was convicted of a crime. In fact, Singh was eligible for denaturalization the moment he
illegally procured citizenship, regardless of whether he ultimately pled guilty to federal crimes
years later.
Now compare this to deportation. Under our immigration laws, being “convicted” of a
wide range of criminal offenses makes an alien immediately “deportable.” E.g., 8 U.S.C.
§ 1227(a)(2)(A)(i) (crimes of moral turpitude); id. § 1227(a)(2)(A)(iii) (aggravated felonies),
§ 1227(a)(2)(B)(i) (offenses involving controlled substances); id. § 1227(a)(2)(C) (firearms
offenses); id. § 1227(a)(2)(E)(i) (domestic-violence crimes, stalking, and child abuse). In other

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words, the alien’s unlawful conduct isn’t enough for him to be deported under those statutes.
Rather, the alien must be convicted of a crime for the government to proceed with deportation
using those provisions. So deportation is “intimately related to the criminal process.” Padilla,
559 U.S. at 365. The same can’t be said for denaturalization.
Granted, a guilty plea may make denaturalization easier. When seeking denaturalization,
the government carries a heavy burden and must offer “clear, unequivocal, and convincing”
evidence. Fedorenko, 449 U.S. at 505 (quotation omitted). A defendant’s previous guilty
plea lightens this burden by preventing him from contesting the facts underlying that conviction.
And those facts may subsequently be used to justify his denaturalization. See Kennedy
v. Mendoza-Martinez, 372 U.S. 144, 157 (1963). However, we’ve never held that counsel must
inform a defendant that a guilty plea could be used against him in a future proceeding. In fact,
we’ve said the opposite, noting that an attorney doesn’t need to advise a defendant that a guilty
plea could be introduced in a subsequent criminal prosecution. King, 17 F.3d at 153–54. If the
Sixth Amendment doesn’t require an attorney to notify a defendant that a guilty plea could be
used against him in a future criminal prosecution with his liberty on the line, it certainly doesn’t
require an attorney to provide such a warning about a potential denaturalization proceeding.
In short, a criminal conviction isn’t “enmeshed” with denaturalization like it is with
deportation. Padilla, 559 U.S. at 365. So the rationale for requiring a defense attorney to advise
his client of the risk of deportation following a guilty plea simply doesn’t apply in the
denaturalization context.
Perhaps recognizing these key distinctions, the Farhane court attempted to reframe
Padilla as requiring an attorney to inform a defendant of “any risk” of deportation following a
guilty plea. Farhane, 121 F.4th at 358 (emphasis added). Because denaturalization may
eventually lead to deportation, the Farhane court reasoned that “[a] risk of denaturalization
simply is a risk of deportation.” Id. at 364. It thus concluded that Padilla requires an attorney to
advise his client of the risk of denaturalization too. Id.
We disagree. For starters, Padilla’s repeated references to “noncitizens” make clear that
its holding doesn’t extend to denaturalization. See, e.g., 559 U.S. at 363–66. And neither does

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its logic. As noted above, Padilla relied on both the severity of deportation and its close
relationship with a criminal conviction. So not just “any risk” of deportation suffices to
implicate the Sixth Amendment. Rather, deportation must be a nearly “automatic result.” Id. at
366. But deportation can hardly be considered an automatic or “virtually inevitable”
consequence of a naturalized citizen’s conviction. Id. at 360. That’s because deportation
depends on the government’s discretionary decision to first initiate denaturalization proceedings.
Plus, an individual facing denaturalization may be able to assert various defenses that aren’t
available to an alien who is convicted of a crime and facing deportation. See Farhane, 121 F.4th
at 391 (Walker, J., dissenting); see also Kungys v. United States, 485 U.S. 759, 780–81 (1988).
In short, deportation isn’t an automatic consequence of a criminal conviction for naturalized
citizens. Thus, Padilla doesn’t require counsel to advise a defendant of the remote and
contingent possibility that he could be denaturalized and then eventually deported after pleading
guilty. The Farhane court therefore erred by trying to shoehorn denaturalization into Padilla’s
holding.
* * *
In sum, counsel isn’t required to advise a defendant that a guilty plea may carry a risk of
denaturalization. We affirm.

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_________________
CONCURRENCE
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GRIFFIN, Circuit Judge, concurring in the judgment. I would not decide the Sixth
Amendment question in the present case because doing so “offends the doctrine that
constitutional questions that need not be addressed should be avoided.” Waters v. Churchill,
511 U.S. 661, 689–90 (1994) (Scalia, J., concurring); Moody v. NetChoice, LLC, 603 U.S. 707,
757 (2024) (Thomas, J., concurring) (“When a federal court decides an issue unnecessary for
resolving a case or controversy, the Judiciary assumes authority beyond what the Constitution
granted.”); see also Spector Motor Serv. v. McLaughlin, 323 U.S. 101, 105 (1944) (“If there is
one doctrine more deeply rooted than any other in the process of constitutional adjudication, it is
that we ought not to pass on questions of constitutionality . . . unless such adjudication is
unavoidable.”).
Here, a narrower, nonconstitutional ground resolves this case: that the district court did
not abuse its discretion in denying Singh’s motion under Federal Rule of Civil Procedure 59(e).
Although the majority’s Sixth Amendment holding may be correct, I would affirm on the Rule
59(e) basis alone. Accordingly, I concur in the judgment only.
I.
My affirmance would take the path advocated by the government. Singh moved for relief
under Rule 59(e), invoking the Second Circuit’s decision in Farhane v. United States, 121 F.4th
353 (2d Cir. 2024) (en banc), as the basis for relitigating his claim for ineffective assistance of
counsel. The district court denied the motion. We are asked to decide whether the district court
abused its discretion in doing so. It did not and, therefore, should be affirmed.
Rule 59(e) allows a court to alter or amend a judgment in narrow circumstances,
including, relevant here, “an intervening change in controlling law,” a “clear error of law,” or “to
prevent manifest injustice.” GenCorp, Inc. v. Am. Int’l Underwriters, 178 F.3d 804, 834 (6th
Cir. 1999) (citation modified). None is present.

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Farhane is not an intervening change in controlling law. Although it was issued after
judgment had been entered against Singh, and is therefore intervening, a decision from the
Second Circuit is not controlling in our circuit. Cross Mountain Coal, Inc. v. Ward, 93 F.3d 211,
217 (6th Cir. 1996).
Singh also has not “clearly establish[ed] a manifest error of law.” Sault Ste. Marie Tribe
of Chippewa Indians v. Engler, 146 F.3d 367, 374 (6th Cir. 1998) (citation modified). Even if
the district court’s ruling on his Rule 59(e) motion contravened Farhane, a Second Circuit case,
again, is not controlling. Thus, it was not a clear error of law for the district court not to follow
Farhane’s holding.
Regarding manifest injustice, we have already held that Singh failed to show a reasonable
probability that he would not have pleaded guilty had counsel advised him about
any denaturalization consequences that might follow. United States v. Singh, 95 F.4th 1028,
1033–34 (6th Cir. 2024). He rehashes this argument now but with nothing new added. Thus, he
once again fails to demonstrate prejudice, which is required to make out a successful claim of
ineffective assistance of counsel. Strickland v. Washington, 466 U.S. 668, 697 (1984). There is
no manifest injustice in disposing of an unsuccessful claim.
II.
In short, a straightforward application of Rule 59(e) resolves this appeal. The majority,
however, chooses to bypass a Rule 59(e) analysis and decide an important Sixth Amendment
issue not argued by the government. Because the majority’s disposition on constitutional
grounds is not necessary, I concur in the judgment only.

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