Jae Lee v. United States , 137 S. Ct. 1958 ( 2017 )

(Slip Opinion) OCTOBER TERM, 2016 1
Syllabus
NOTE: Where it is feasible, a syllabus (headnote) will be released, as is
being done in connection with this case, at the time the opinion is issued.
The syllabus constitutes no part of the opinion of the Court but has been
prepared by the Reporter of Decisions for the convenience of the reader.
See United States v. Detroit Timber & Lumber Co., 200 U.S. 321, 337.
SUPREME COURT OF THE UNITED STATES
Syllabus
JAE LEE v. UNITED STATES
CERTIORARI TO THE UNITED STATES COURT OF APPEALS FOR
THE SIXTH CIRCUIT
No. 16–327. Argued March 28, 2017—Decided June 23, 2017
Petitioner Jae Lee moved to the United States from South Korea with
his parents when he was 13. In the 35 years he has spent in this
country, he has never returned to South Korea, nor has he become a
U. S. citizen, living instead as a lawful permanent resident. In 2008,
federal officials received a tip from a confidential informant that Lee
had sold the informant ecstasy and marijuana. After obtaining a
warrant, the officials searched Lee’s house, where they found drugs,
cash, and a loaded rifle. Lee admitted that the drugs were his, and a
grand jury indicted him on one count of possessing ecstasy with in-
tent to distribute. Lee retained counsel and entered into plea discus-
sions with the Government. During the plea process, Lee repeatedly
asked his attorney whether he would face deportation; his attorney
assured him that he would not be deported as a result of pleading
guilty. Based on that assurance, Lee accepted a plea and was sen-
tenced to a year and a day in prison. Lee had in fact pleaded guilty to
an “aggravated felony” under the Immigration and Nationality Act, 8
U.S. C. §1101(a)(43)(B), so he was, contrary to his attorney’s advice,
subject to mandatory deportation as a result of that plea. See
§1227(a)(2)(A)(iii). When Lee learned of this consequence, he filed a
motion to vacate his conviction and sentence, arguing that his attor-
ney had provided constitutionally ineffective assistance. At an evi-
dentiary hearing, both Lee and his plea-stage counsel testified that
“deportation was the determinative issue” to Lee in deciding whether
to accept a plea, and Lee’s counsel acknowledged that although Lee’s
defense to the charge was weak, if he had known Lee would be de-
ported upon pleading guilty, he would have advised him to go to trial.
A Magistrate Judge recommended that Lee’s plea be set aside and his
conviction vacated. The District Court, however, denied relief, and
2 JAE LEE v. UNITED STATES
Syllabus
the Sixth Circuit affirmed. Applying the two-part test for ineffective
assistance claims from Strickland v. Washington, 466 U.S. 668, the
Sixth Circuit concluded that, while the Government conceded that
Lee’s counsel had performed deficiently, Lee could not show that he
was prejudiced by his attorney’s erroneous advice.
Held: Lee has demonstrated that he was prejudiced by his counsel’s
erroneous advice. Pp. 5–13.
(a) When a defendant claims that his counsel’s deficient perfor-
mance deprived him of a trial by causing him to accept a plea, the de-
fendant can show prejudice by demonstrating a “reasonable probabil-
ity that, but for counsel’s errors, he would not have pleaded guilty
and would have insisted on going to trial.” Hill v. Lockhart, 474 U.S.
52, 59.
Lee contends that he can make this showing because he never
would have accepted a guilty plea had he known the result would be
deportation. The Government contends that Lee cannot show preju-
dice from accepting a plea where his only hope at trial was that
something unexpected and unpredictable might occur that would lead
to acquittal. Pp. 5–8.
(b) The Government makes two errors in urging the adoption of a
per se rule that a defendant with no viable defense cannot show prej-
udice from the denial of his right to trial. First, it forgets that cate-
gorical rules are ill suited to an inquiry that demands a “case-by-case
examination” of the “totality of the evidence.” Williams v. Taylor,
529 U.S. 362, 391 (internal quotation marks omitted); Strickland,
466 U.S., at 695. More fundamentally, it overlooks that the Hill v.
Lockhart inquiry focuses on a defendant’s decisionmaking, which
may not turn solely on the likelihood of conviction after trial.
The decision whether to plead guilty also involves assessing the re-
spective consequences of a conviction after trial and by plea. See INS
v. St. Cyr, 533 U.S. 289, 322–323. When those consequences are,
from the defendant’s perspective, similarly dire, even the smallest
chance of success at trial may look attractive. For Lee, deportation
after some time in prison was not meaningfully different from depor-
tation after somewhat less time; he says he accordingly would have
rejected any plea leading to deportation in favor of throwing a “Hail
Mary” at trial. Pointing to Strickland, the Government urges that
“[a] defendant has no entitlement to the luck of a lawless deci-
sionmaker.” 466 U.S., at 695. That statement, however, was made
in the context of discussing the presumption of reliability applied to
judicial proceedings, which has no place where, as here, a defendant
was deprived of a proceeding altogether. When the inquiry is focused
on what an individual defendant would have done, the possibility of
even a highly improbable result may be pertinent to the extent it
Cite as: 582 U. S. ____ (2017) 3
Syllabus
would have affected the defendant’s decisionmaking. Pp. 8–10.
(c) Courts should not upset a plea solely because of post hoc asser-
tions from a defendant about how he would have pleaded but for his
attorney’s deficiencies. Rather, they should look to contemporaneous
evidence to substantiate a defendant’s expressed preferences. In the
unusual circumstances of this case, Lee has adequately demonstrated
a reasonable probability that he would have rejected the plea had he
known that it would lead to mandatory deportation: Both Lee and his
attorney testified that “deportation was the determinative issue” to
Lee; his responses during his plea colloquy confirmed the importance
he placed on deportation; and he had strong connections to the Unit-
ed States, while he had no ties to South Korea.
The Government argues that Lee cannot “convince the court that a
decision to reject the plea bargain would have been rational under
the circumstances,” Padilla v. Kentucky, 559 U.S. 356, 372, since de-
portation would almost certainly result from a trial. Unlike the Gov-
ernment, this Court cannot say that it would be irrational for some-
one in Lee’s position to risk additional prison time in exchange for
holding on to some chance of avoiding deportation. Pp. 10–13.
825 F.3d 311, reversed and remanded.
ROBERTS, C. J., delivered the opinion of the Court, in which KENNEDY,
GINSBURG, BREYER, SOTOMAYOR, and KAGAN, JJ., joined. THOMAS, J.,
filed a dissenting opinion, in which ALITO, J., joined except as to Part I.
GORSUCH, J., took no part in the consideration or decision of the case.
Cite as: 582 U. S. ____ (2017) 1
Opinion of the Court
NOTICE: This opinion is subject to formal revision before publication in the
preliminary print of the United States Reports. Readers are requested to
notify the Reporter of Decisions, Supreme Court of the United States, Wash-
ington, D. C. 20543, of any typographical or other formal errors, in order
that corrections may be made before the preliminary print goes to press.
SUPREME COURT OF THE UNITED STATES
_________________
No. 16–327
_________________
JAE LEE, PETITIONER v. UNITED STATES
ON WRIT OF CERTIORARI TO THE UNITED STATES COURT OF
APPEALS FOR THE SIXTH CIRCUIT
[June 23, 2017]
CHIEF JUSTICE ROBERTS delivered the opinion of the
Court.
Petitioner Jae Lee was indicted on one count of pos-
sessing ecstasy with intent to distribute. Although he has
lived in this country for most of his life, Lee is not a United
States citizen, and he feared that a criminal conviction
might affect his status as a lawful permanent resident.
His attorney assured him there was nothing to worry
about—the Government would not deport him if he pleaded
guilty. So Lee, who had no real defense to the charge,
opted to accept a plea that carried a lesser prison sentence
than he would have faced at trial.
Lee’s attorney was wrong: The conviction meant that
Lee was subject to mandatory deportation from this coun-
try. Lee seeks to vacate his conviction on the ground that,
in accepting the plea, he received ineffective assistance of
counsel in violation of the Sixth Amendment. Everyone
agrees that Lee received objectively unreasonable repre-
sentation. The question presented is whether he can show
he was prejudiced as a result.
I
Jae Lee moved to the United States from South Korea in
2 JAE LEE v. UNITED STATES
Opinion of the Court
1982. He was 13 at the time. His parents settled the
family in New York City, where they opened a small coffee
shop. After graduating from a business high school in
Manhattan, Lee set out on his own to Memphis, Tennes-
see, where he started working at a restaurant. After three
years, Lee decided to try his hand at running a business.
With some assistance from his family, Lee opened the
Mandarin Palace Chinese Restaurant in a Memphis sub-
urb. The Mandarin was a success, and Lee eventually
opened a second restaurant nearby. In the 35 years he
has spent in the country, Lee has never returned to South
Korea. He did not become a United States citizen, living
instead as a lawful permanent resident.
At the same time he was running his lawful businesses,
Lee also engaged in some illegitimate activity. In 2008, a
confidential informant told federal officials that Lee had
sold the informant approximately 200 ecstasy pills and
two ounces of hydroponic marijuana over the course of
eight years. The officials obtained a search warrant for
Lee’s house, where they found 88 ecstasy pills, three Valium
tablets, $32,432 in cash, and a loaded rifle. Lee admitted
that the drugs were his and that he had given ecstasy to
his friends.
A grand jury indicted Lee on one count of possessing
ecstasy with intent to distribute in violation of 21 U.S. C.
§841(a)(1). Lee retained an attorney and entered into plea
discussions with the Government. The attorney advised
Lee that going to trial was “very risky” and that, if he
pleaded guilty, he would receive a lighter sentence than he
would if convicted at trial. App. 167. Lee informed his
attorney of his noncitizen status and repeatedly asked him
whether he would face deportation as a result of the crim-
inal proceedings. The attorney told Lee that he would not
be deported as a result of pleading guilty. Lee v. United
States, 825 F.3d 311, 313 (CA6 2016). Based on that
assurance, Lee accepted the plea and the District Court
Cite as: 582 U. S. ____ (2017) 3
Opinion of the Court
sentenced him to a year and a day in prison, though it
deferred commencement of Lee’s sentence for two months
so that Lee could manage his restaurants over the holiday
season.
Lee quickly learned, however, that a prison term was
not the only consequence of his plea. Lee had pleaded
guilty to what qualifies as an “aggravated felony” under
the Immigration and Nationality Act, and a noncitizen
convicted of such an offense is subject to mandatory depor-
tation. See 8 U.S. C. §§1101(a)(43)(B), 1227(a)(2)(A)(iii);
Calcano-Martinez v. INS, 533 U.S. 348, 350, n. 1 (2001).
Upon learning that he would be deported after serving his
sentence, Lee filed a motion under 28 U.S. C. §2255 to
vacate his conviction and sentence, arguing that his attor-
ney had provided constitutionally ineffective assistance.
At an evidentiary hearing on Lee’s motion, both Lee and
his plea-stage counsel testified that “deportation was the
determinative issue in Lee’s decision whether to accept the
plea.” Report and Recommendation in No. 2:10–cv–02698
(WD Tenn.), pp. 6–7 (Report and Recommendation). In
fact, Lee explained, his attorney became “pretty upset
because every time something comes up I always ask
about immigration status,” and the lawyer “always said
why [are you] worrying about something that you don’t
need to worry about.” App. 170. According to Lee, the
lawyer assured him that if deportation was not in the plea
agreement, “the government cannot deport you.” Ibid.
Lee’s attorney testified that he thought Lee’s case was a
“bad case to try” because Lee’s defense to the charge was
weak. Id., at 218–219. The attorney nonetheless
acknowledged that if he had known Lee would be deported
upon pleading guilty, he would have advised him to go to
trial. Id., at 236, 244. Based on the hearing testimony, a
Magistrate Judge recommended that Lee’s plea be set
aside and his conviction vacated because he had received
ineffective assistance of counsel.
4 JAE LEE v. UNITED STATES
Opinion of the Court
The District Court, however, denied relief. Applying our
two-part test for ineffective assistance claims from Strick-
land v. Washington, 466 U.S. 668 (1984), the District
Court concluded that Lee’s counsel had performed defi-
ciently by giving improper advice about the deportation
consequences of the plea. But, “[i]n light of the over-
whelming evidence of Lee’s guilt,” Lee “would have almost
certainly” been found guilty and received “a significantly
longer prison sentence, and subsequent deportation,” had
he gone to trial. Order in No. 2:10–cv–02698 (WD Tenn.),
p. 24 (Order). Lee therefore could not show he was
prejudiced by his attorney’s erroneous advice. Viewing
its resolution of the issue as debatable among jurists
of reason, the District Court granted a certificate of
appealability.
The Court of Appeals for the Sixth Circuit affirmed the
denial of relief. On appeal, the Government conceded that
the performance of Lee’s attorney had been deficient. To
establish that he was prejudiced by that deficient perfor-
mance, the court explained, Lee was required to show “a
reasonable probability that, but for counsel’s errors, he
would not have pleaded guilty and would have insisted on
going to trial.” 825 F.3d, at 313 (quoting Hill v. Lockhart,
474 U.S. 52, 59 (1985); internal quotation marks omitted).
Lee had “no bona fide defense, not even a weak one,” so he
“stood to gain nothing from going to trial but more prison
time.” 825 F.3d, at 313, 316. Relying on Circuit prece-
dent holding that “no rational defendant charged with a
deportable offense and facing overwhelming evidence of
guilt would proceed to trial rather than take a plea deal
with a shorter prison sentence,” the Court of Appeals
concluded that Lee could not show prejudice. Id., at 314
(internal quotation marks omitted). We granted certiorari.
580 U. S. ___ (2016).
Cite as: 582 U. S. ____ (2017)
5
Opinion of the Court
II
The Sixth Amendment guarantees a defendant the
effective assistance of counsel at “critical stages of a crim-
inal proceeding,” including when he enters a guilty plea.
Lafler v. Cooper, 566 U.S. 156, 165 (2012); Hill, 474 U.S.,
at 58. To demonstrate that counsel was constitutionally
ineffective, a defendant must show that counsel’s repre-
sentation “fell below an objective standard of reasonable-
ness” and that he was prejudiced as a result. Strickland,
466 U.S., at 688, 692. The first requirement is not at
issue in today’s case: The Government concedes that Lee’s
plea-stage counsel provided inadequate representation
when he assured Lee that he would not be deported if he
pleaded guilty. Brief for United States 15. The question
is whether Lee can show he was prejudiced by that erro-
neous advice.
A
A claim of ineffective assistance of counsel will often
involve a claim of attorney error “during the course of a
legal proceeding”—for example, that counsel failed to raise
an objection at trial or to present an argument on appeal.
Roe v. Flores-Ortega, 528 U.S. 470, 481 (2000). A defend-
ant raising such a claim can demonstrate prejudice by
showing “a reasonable probability that, but for counsel’s
unprofessional errors, the result of the proceeding would
have been different.” Id., at 482 (quoting Strickland, 466
U.S., at 694; internal quotation marks omitted).
But in this case counsel’s “deficient performance arguably
led not to a judicial proceeding of disputed reliability,
but rather to the forfeiture of a proceeding itself.” Flores-
Ortega, 528 U.S., at 483. When a defendant alleges his
counsel’s deficient performance led him to accept a guilty
plea rather than go to trial, we do not ask whether, had he
gone to trial, the result of that trial “would have been
different” than the result of the plea bargain. That is
6 JAE LEE v. UNITED STATES
Opinion of the Court
because, while we ordinarily “apply a strong presumption
of reliability to judicial proceedings,” “we cannot accord”
any such presumption “to judicial proceedings that never
took place.” Id., at 482–483 (internal quotation marks
omitted).
We instead consider whether the defendant was preju-
diced by the “denial of the entire judicial proceeding . . . to
which he had a right.” Id., at 483. As we held in Hill v.
Lockhart, when a defendant claims that his counsel’s
deficient performance deprived him of a trial by causing
him to accept a plea, the defendant can show prejudice by
demonstrating a “reasonable probability that, but for
counsel’s errors, he would not have pleaded guilty and
would have insisted on going to trial.” 474 U.S., at 59.
The dissent contends that a defendant must also show
that he would have been better off going to trial. That is
true when the defendant’s decision about going to trial
turns on his prospects of success and those are affected by
the attorney’s error—for instance, where a defendant
alleges that his lawyer should have but did not seek to
suppress an improperly obtained confession. Premo v.
Moore, 562 U.S. 115, 118 (2011); cf., e.g., Hill, 474 U.S.,
at 59 (discussing failure to investigate potentially exculpa-
tory evidence).
Not all errors, however, are of that sort. Here Lee knew,
correctly, that his prospects of acquittal at trial were grim,
and his attorney’s error had nothing to do with that. The
error was instead one that affected Lee’s understanding of
the consequences of pleading guilty. The Court confronted
precisely this kind of error in Hill. See id., at 60 (“the
claimed error of counsel is erroneous advice as to eligibil-
ity for parole”). Rather than asking how a hypothetical
trial would have played out absent the error, the Court
considered whether there was an adequate showing that
the defendant, properly advised, would have opted to go to
trial. The Court rejected the defendant’s claim because he
Cite as: 582 U. S. ____ (2017) 7
Opinion of the Court
had “alleged no special circumstances that might support
the conclusion that he placed particular emphasis on his
parole eligibility in deciding whether or not to plead
guilty.” Ibid.1
Lee, on the other hand, argues he can establish preju-
dice under Hill because he never would have accepted a
guilty plea had he known that he would be deported as a
result. Lee insists he would have gambled on trial, risking
more jail time for whatever small chance there might be of
an acquittal that would let him remain in the United
States.2 The Government responds that, since Lee had no
viable defense at trial, he would almost certainly have lost
and found himself still subject to deportation, with a
——————
1 The dissent also relies heavily on Missouri v. Frye, 566 U.S. 134
(2012), and Lafler v. Cooper, 566 U.S. 156 (2012). Those cases involved
defendants who alleged that, but for their attorney’s incompetence,
they would have accepted a plea deal—not, as here and as in Hill, that
they would have rejected a plea. In both Frye and Lafler, the Court
highlighted this difference: Immediately following the sentence that the
dissent plucks from Frye, post, at 5 (opinion of THOMAS, J.), the Court
explained that its “application of Strickland to the instances of an
uncommunicated, lapsed plea does nothing to alter the standard laid
out in Hill.” 566 U.S., at 148 (“Hill was correctly decided and applies
in the context in which it arose”). Lafler, decided the same day as Frye,
reiterated that “[i]n contrast to Hill, here the ineffective advice led not
to an offer’s acceptance but to its rejection.” 566 U.S., at 163. Frye and
Lafler articulated a different way to show prejudice, suited to the
context of pleas not accepted, not an additional element to the Hill
inquiry. See Frye, 566 U.S., at 148 (“Hill does not . . . provide the sole
means for demonstrating prejudice arising from the deficient perfor-
mance of counsel during plea negotiations”). Contrary to the dissent’s
assertion, post, at 8–9, we do not depart from Strickland’s requirement
of prejudice. The issue is how the required prejudice may be shown.
2 Lee also argues that he can show prejudice because, had his attor-
ney advised him that he would be deported if he accepted the Govern-
ment’s plea offer, he would have bargained for a plea deal that did not
result in certain deportation. Given our conclusion that Lee can show
prejudice based on the reasonable probability that he would have gone
to trial, we need not reach this argument.
8 JAE LEE v. UNITED STATES
Opinion of the Court
lengthier prison sentence to boot. Lee, the Government
contends, cannot show prejudice from accepting a plea
where his only hope at trial was that something unex-
pected and unpredictable might occur that would lead to
an acquittal.
B
The Government asks that we, like the Court of Appeals
below, adopt a per se rule that a defendant with no viable
defense cannot show prejudice from the denial of his right
to trial. Brief for United States 26. As a general matter,
it makes sense that a defendant who has no realistic
defense to a charge supported by sufficient evidence will
be unable to carry his burden of showing prejudice from
accepting a guilty plea. But in elevating this general
proposition to a per se rule, the Government makes two
errors. First, it forgets that categorical rules are ill suited
to an inquiry that we have emphasized demands a “case-
by-case examination” of the “totality of the evidence.”
Williams v. Taylor, 529 U.S. 362, 391 (2000) (internal
quotation marks omitted); Strickland, 466 U.S., at 695.
And, more fundamentally, the Government overlooks that
the inquiry we prescribed in Hill v. Lockhart focuses on a
defendant’s decisionmaking, which may not turn solely on
the likelihood of conviction after trial.
A defendant without any viable defense will be highly
likely to lose at trial. And a defendant facing such long
odds will rarely be able to show prejudice from accepting a
guilty plea that offers him a better resolution than would
be likely after trial. But that is not because the prejudice
inquiry in this context looks to the probability of a convic-
tion for its own sake. It is instead because defendants
obviously weigh their prospects at trial in deciding
whether to accept a plea. See Hill, 474 U.S., at 59.
Where a defendant has no plausible chance of an acquittal
at trial, it is highly likely that he will accept a plea if the
Cite as: 582 U. S. ____ (2017) 9
Opinion of the Court
Government offers one.
But common sense (not to mention our precedent) rec-
ognizes that there is more to consider than simply the
likelihood of success at trial. The decision whether to
plead guilty also involves assessing the respective conse-
quences of a conviction after trial and by plea. See INS v.
St. Cyr, 533 U.S. 289, 322–323 (2001). When those conse-
quences are, from the defendant’s perspective, similarly
dire, even the smallest chance of success at trial may look
attractive. For example, a defendant with no realistic
defense to a charge carrying a 20-year sentence may nev-
ertheless choose trial, if the prosecution’s plea offer is 18
years. Here Lee alleges that avoiding deportation was the
determinative factor for him; deportation after some time
in prison was not meaningfully different from deportation
after somewhat less time. He says he accordingly would
have rejected any plea leading to deportation—even if it
shaved off prison time—in favor of throwing a “Hail Mary”
at trial.
The Government urges that, in such circumstances, the
possibility of an acquittal after trial is “irrelevant to the
prejudice inquiry,” pointing to our statement in Strickland
that “[a] defendant has no entitlement to the luck of a
lawless decisionmaker.” 466 U.S., at 695. That state-
ment, however, was made in the context of discussing the
presumption of reliability we apply to judicial proceedings.
As we have explained, that presumption has no place
where, as here, a defendant was deprived of a proceeding
altogether. Flores-Ortega, 528 U.S., at 483. In a pre-
sumptively reliable proceeding, “the possibility of arbitrar-
iness, whimsy, caprice, ‘nullification,’ and the like” must
by definition be ignored. Strickland, 466 U.S., at 695.
But where we are instead asking what an individual
defendant would have done, the possibility of even a highly
improbable result may be pertinent to the extent it
10 JAE LEE v. UNITED STATES
Opinion of the Court
would have affected his decisionmaking.3
C
“Surmounting Strickland’s high bar is never an easy
task,” Padilla v. Kentucky, 559 U.S. 356, 371 (2010), and
the strong societal interest in finality has “special force
with respect to convictions based on guilty pleas.” United
States v. Timmreck, 441 U.S. 780, 784 (1979). Courts
should not upset a plea solely because of post hoc asser-
tions from a defendant about how he would have pleaded
but for his attorney’s deficiencies. Judges should instead
look to contemporaneous evidence to substantiate a de-
fendant’s expressed preferences.
In the unusual circumstances of this case, we conclude
that Lee has adequately demonstrated a reasonable prob-
ability that he would have rejected the plea had he known
that it would lead to mandatory deportation. There is no
question that “deportation was the determinative issue in
Lee’s decision whether to accept the plea deal.” Report
and Recommendation, at 6–7; see also Order, at 14 (noting
Government did not dispute testimony to this effect). Lee
asked his attorney repeatedly whether there was any risk
of deportation from the proceedings, and both Lee and his
——————
3 The dissent makes much of the fact that Hill v. Lockhart, 474 U.S.
52 (1985), also noted that courts should ignore the “idiosyncrasies of the
particular decisionmaker.” Post, at 7 (quoting Hill, 474 U.S., at 60;
internal quotation marks omitted). But Hill made this statement in
discussing how courts should analyze “predictions of the outcome at a
possible trial.” Id., at 59–60. As we have explained, assessing the
effect of some types of attorney errors on defendants’ decisionmaking
involves such predictions: Where an attorney error allegedly affects
how a trial would have played out, we analyze that error’s effects on a
defendant’s decisionmaking by making a prediction of the likely trial
outcome. But, as Hill recognized, such predictions will not always be
“necessary.” Id., at 60. Such a prediction is neither necessary nor
appropriate where, as here, the error is one that is not alleged to be
pertinent to a trial outcome, but is instead alleged to have affected a
defendant’s understanding of the consequences of his guilty plea.
Cite as: 582 U. S. ____ (2017) 11
Opinion of the Court
attorney testified at the evidentiary hearing below that
Lee would have gone to trial if he had known about the
deportation consequences. See Report and Recommenda-
tion, at 12 (noting “the undisputed fact that had Lee at all
been aware that deportation was possible as a result of his
guilty plea, he would . . . not have pled guilty”), adopted in
relevant part in Order, at 15.
Lee demonstrated as much at his plea colloquy: When
the judge warned him that a conviction “could result in
your being deported,” and asked “[d]oes that at all affect
your decision about whether you want to plead guilty or
not,” Lee answered “Yes, Your Honor.” App. 103. When
the judge inquired “[h]ow does it affect your decision,” Lee
responded “I don’t understand,” and turned to his attorney
for advice. Ibid. Only when Lee’s counsel assured him
that the judge’s statement was a “standard warning” was
Lee willing to proceed to plead guilty. Id., at 210.4
There is no reason to doubt the paramount importance
Lee placed on avoiding deportation. Deportation is always
“a particularly severe penalty,” Padilla, 559 U.S., at 365
(internal quotation marks omitted), and we have “recog-
nized that ‘preserving the client’s right to remain in the
United States may be more important to the client than
any potential jail sentence,’ ” id., at 368 (quoting St. Cyr,
533 U.S., at 322; alteration and some internal quotation
——————
4 Several courts have noted that a judge’s warnings at a plea colloquy
may undermine a claim that the defendant was prejudiced by his
attorney’s misadvice. See, e.g., United States v. Newman, 805 F.3d
1143, 1147 (CADC 2015); United States v. Kayode, 777 F.3d 719, 728–
729 (CA5 2014); United States v. Akinsade, 686 F.3d 248, 253 (CA4
2012); Boyd v. Yukins, 99 Fed. Appx. 699, 705 (CA6 2004). The present
case involves a claim of ineffectiveness of counsel extending to advice
specifically undermining the judge’s warnings themselves, which the
defendant contemporaneously stated on the record he did not under-
stand. There has been no suggestion here that the sentencing judge’s
statements at the plea colloquy cured any prejudice from the erroneous
advice of Lee’s counsel.
12 JAE LEE v. UNITED STATES
Opinion of the Court
marks omitted); see also Padilla, 559 U.S., at 364
(“[D]eportation is an integral part—indeed, sometimes the
most important part—of the penalty that may be imposed
on noncitizen defendants who plead guilty to specified
crimes.” (footnote omitted)). At the time of his plea, Lee
had lived in the United States for nearly three decades,
had established two businesses in Tennessee, and was the
only family member in the United States who could care
for his elderly parents—both naturalized American citi-
zens. In contrast to these strong connections to the United
States, there is no indication that he had any ties to South
Korea; he had never returned there since leaving as a
child.
The Government argues, however, that under Padilla v.
Kentucky, a defendant “must convince the court that a
decision to reject the plea bargain would have been rational
under the circumstances.” Id., at 372. The Government
contends that Lee cannot make that showing because he
was going to be deported either way; going to trial would
only result in a longer sentence before that inevitable
consequence. See Brief for United States 13, 21–23.
We cannot agree that it would be irrational for a de-
fendant in Lee’s position to reject the plea offer in favor of
trial. But for his attorney’s incompetence, Lee would have
known that accepting the plea agreement would certainly
lead to deportation. Going to trial? Almost certainly. If
deportation were the “determinative issue” for an individ-
ual in plea discussions, as it was for Lee; if that individual
had strong connections to this country and no other, as did
Lee; and if the consequences of taking a chance at trial
were not markedly harsher than pleading, as in this case,
that “almost” could make all the difference. Balanced
against holding on to some chance of avoiding deportation
was a year or two more of prison time. See id., at 6. Not
everyone in Lee’s position would make the choice to reject
the plea. But we cannot say it would be irrational to do so.
Cite as: 582 U. S. ____ (2017) 13
Opinion of the Court
Lee’s claim that he would not have accepted a plea had
he known it would lead to deportation is backed by sub-
stantial and uncontroverted evidence. Accordingly we
conclude Lee has demonstrated a “reasonable probability
that, but for [his] counsel’s errors, he would not have
pleaded guilty and would have insisted on going to trial.”
Hill, 474 U.S., at 59.
* * *
The judgment of the United States Court of Appeals for
the Sixth Circuit is reversed, and the case is remanded for
further proceedings consistent with this opinion.
It is so ordered.
JUSTICE GORSUCH took no part in the consideration or
decision of this case.
Cite as: 582 U. S. ____ (2017) 1
THOMAS, J., dissenting
SUPREME COURT OF THE UNITED STATES
_________________
No. 16–327
_________________
JAE LEE, PETITIONER v. UNITED STATES
ON WRIT OF CERTIORARI TO THE UNITED STATES COURT OF
APPEALS FOR THE SIXTH CIRCUIT
[June 23, 2017]
JUSTICE THOMAS, with whom JUSTICE ALITO joins ex-
cept for Part I, dissenting.
The Court today holds that a defendant can undo a
guilty plea, well after sentencing and in the face of over-
whelming evidence of guilt, because he would have chosen
to pursue a defense at trial with no reasonable chance of
success if his attorney had properly advised him of the
immigration consequences of his plea. Neither the Sixth
Amendment nor this Court’s precedents support that
conclusion. I respectfully dissent.
I
As an initial matter, I remain of the view that the Sixth
Amendment to the Constitution does not “requir[e] coun-
sel to provide accurate advice concerning the potential
removal consequences of a guilty plea.” Padilla v. Ken-
tucky, 559 U.S. 356, 388 (2010) (Scalia, J., joined by
THOMAS, J., dissenting). I would therefore affirm the
Court of Appeals on the ground that the Sixth Amendment
does not apply to the allegedly ineffective assistance in
this case.
II
Because the Court today announces a novel standard for
prejudice at the plea stage, I further dissent on the sepa-
rate ground that its standard does not follow from our
precedents.
2 JAE LEE v. UNITED STATES
THOMAS, J., dissenting
A
The Court and both of the parties agree that the preju-
dice inquiry in this context is governed by Strickland v.
Washington, 466 U.S. 668 (1984). See ante, at 5; Brief for
Petitioner 16; Brief for United States 15. The Court in
Strickland held that a defendant may establish a claim of
ineffective assistance of counsel by showing that his
“counsel’s representation fell below an objective standard
of reasonableness” and, as relevant here, that the repre-
sentation prejudiced the defendant by “actually ha[ving]
an adverse effect on the defense.” 466 U.S., at 688, 693.
To establish prejudice under Strickland, a defendant
must show a “reasonable probability that, but for counsel’s
unprofessional errors, the result of the proceeding would
have been different.” Id., at 694. Strickland made clear
that the “result of the proceeding” refers to the outcome of
the defendant’s criminal prosecution as a whole. It de-
fined “reasonable probability” as “a probability sufficient
to undermine confidence in the outcome.” Ibid. (emphasis
added). And it explained that “[a]n error by counsel . . .
does not warrant setting aside the judgment of a criminal
proceeding if the error had no effect on the judgment.” Id.,
at 691 (emphasis added).
The parties agree that this inquiry assumes an “objec-
tive” decisionmaker. Brief for Petitioner 17; Brief for
United States 17. That conclusion also follows directly
from Strickland. According to Strickland, the “assessment
of the likelihood of a result more favorable to the defend-
ant must exclude the possibility of arbitrariness, whimsy,
caprice, ‘nullification,’ and the like.” 466 U.S., at 695. It
does not depend on subjective factors such as “the idiosyn-
crasies of the particular decisionmaker,” including the
decisionmaker’s “unusual propensities toward harshness
or leniency.” Ibid. These factors are flatly “irrelevant to
the prejudice inquiry.” Ibid. In other words, “[a] defend-
ant has no entitlement to the luck of a lawless deci-
Cite as: 582 U. S. ____ (2017) 3
THOMAS, J., dissenting
sionmaker.” Ibid. Instead, “[t]he assessment of prejudice
should proceed on the assumption that the decisionmaker
is reasonably, conscientiously, and impartially applying
the standards that govern the decision.” Ibid.
When the Court extended the right to effective counsel
to the plea stage, see Hill v. Lockhart, 474 U.S. 52 (1985),
it held that “the same two-part standard” from Strickland
applies. 474 U.S., at 57 (repeating Strickland’s teaching
that even an unreasonable error by counsel “ ‘does not
warrant setting aside the judgment’ ” so long as the error
“ ‘had no effect on the judgment’ ” (quoting 466 U.S., at
691)). To be sure, the Court said—and the majority today
emphasizes—that a defendant asserting an ineffectiveness
claim at the plea stage “must show that there is a reason-
able probability that, but for counsel’s errors, he would not
have pleaded guilty and would have insisted on going to
trial.” 474 U.S., at 59. But that requirement merely
reflects the reality that a defendant cannot show that the
outcome of his case would have been different if he would
have accepted his current plea anyway.* In other words,
the defendant’s ability to show that he would have gone to
trial is necessary, but not sufficient, to establish prejudice.
The Hill Court went on to explain that Strickland’s two-
part test applies the same way in the plea context as in
other contexts. In particular, the “assessment” will pri-
marily turn on “a prediction whether,” in the absence of
counsel’s error, “the evidence” of the defendant’s innocence
or guilt “likely would have changed the outcome” of the
proceeding. 474 U.S., at 59. Thus, a defendant cannot
——————
* It is not enough for a defendant to show that he would have obtained
a better plea agreement. “[A] defendant has no right to be offered a
plea,” Missouri v. Frye, 566 U.S. 134, 148 (2012); Lafler v. Cooper, 566
U.S. 156, 168 (2012), and this Court has never concluded that a de-
fendant could show a “reasonable probability” of a different result
based on a purely hypothetical plea offer subject to absolute executive
discretion.
4 JAE LEE v. UNITED STATES
THOMAS, J., dissenting
show prejudice where it is “ ‘inconceivable’ ” not only that
he would have gone to trial, but also “ ‘that if he had done
so he either would have been acquitted or, if convicted,
would nevertheless have been given a shorter sentence
than he actually received.’ ” Ibid. (quoting Evans v. Meyer,
742 F.2d 371, 375 (CA7 1984) (emphasis added)). In sum,
the proper inquiry requires a defendant to show both that
he would have rejected his plea and gone to trial and that
he would likely have obtained a more favorable result in
the end.
To the extent Hill was ambiguous about the standard,
our precedents applying it confirm this interpretation. In
Premo v. Moore, 562 U.S. 115 (2011), the Court empha-
sized that “strict adherence to the Strickland standard” is
“essential” when reviewing claims about attorney error “at
the plea bargain stage.” Id., at 125. In that case, the
defendant argued that his counsel was constitutionally
ineffective because he had failed to seek suppression of his
confession before he pleaded no contest. In analyzing the
prejudice issue, the Court did not focus solely on whether
the suppression hearing would have turned out differ-
ently, or whether the defendant would have chosen to go to
trial. It focused as well on the weight of the evidence
against the defendant and the fact that he likely would not
have obtained a more favorable result at trial, regardless
of whether he succeeded at the suppression hearing. See
id., at 129 (describing the State’s case as “formidable” and
observing that “[t]he bargain counsel struck” in the plea
agreement was “a favorable one” to the defendant com-
pared to what might have happened at trial).
The Court in Missouri v. Frye, 566 U.S. 134 (2012), took
a similar approach. In that case, the Court extended Hill
to hold that counsel could be constitutionally ineffective
for failing to communicate a plea deal to a defendant. 566
U.S., at 145. The Court emphasized that, in addition to
showing a reasonable probability that the defendant
Cite as: 582 U. S. ____ (2017) 5
THOMAS, J., dissenting
“would have accepted the earlier plea offer,” it is also
“necessary” to show a “reasonable probability that the end
result of the criminal process would have been more fa-
vorable by reason of a plea to a lesser charge or a sentence
of less prison time.” Id., at 147; see also id., at 150 (the
defendant “must show not only a reasonable probability
that he would have accepted the lapsed plea but also a
reasonable probability that the prosecution would have
adhered to the agreement and that it would have been
accepted by the trial court” (emphasis added)). In short,
the Court did not focus solely on whether the defendant
would have accepted the plea. It instead required the
defendant to show that the ultimate outcome would have
been different.
Finally, the Court’s decision in Lafler v. Cooper, 566
U.S. 156 (2012), is to the same effect. In that case, the
Court concluded that counsel may be constitutionally
ineffective by causing a defendant to reject a plea deal he
should have accepted. Id., at 164. The Court again em-
phasized that the prejudice inquiry requires a showing
that the criminal prosecution would ultimately have ended
differently for the defendant—not merely that the defend-
ant would have accepted the deal. The Court stated that
the defendant in those circumstances “must show” a rea-
sonable probability that “the conviction or sentence, or
both, under the offer’s terms would have been less severe
than under the judgment and sentence that in fact were
imposed.” Ibid.
These precedents are consistent with our cases govern-
ing the right to effective assistance of counsel in other
contexts. This Court has held that the right to effective
counsel applies to all “critical stages of the criminal pro-
ceedings.” Montejo v. Louisiana, 556 U.S. 778, 786 (2009)
(internal quotation marks omitted). Those stages include
not only “the entry of a guilty plea,” but also “arraign-
ments, postindictment interrogation, [and] postindictment
6 JAE LEE v. UNITED STATES
THOMAS, J., dissenting
lineups.” Frye, supra, at 140 (citing cases). In those cir-
cumstances, the Court has not held that the prejudice
inquiry focuses on whether that stage of the proceeding
would have ended differently. It instead has made clear
that the prejudice inquiry is the same as in Strickland,
which requires a defendant to establish that he would
have been better off in the end had his counsel not erred.
See 466 U.S., at 694.
B
The majority misapplies this Court’s precedents when it
concludes that a defendant may establish prejudice by
showing only that “he would not have pleaded guilty and
would have insisted on going to trial,” without showing
that “the result of that trial would have been different
than the result of the plea bargain.” Ante, at 5, 6 (internal
quotation marks omitted). In reaching this conclusion, the
Court relies almost exclusively on the single line from Hill
that “the defendant must show that there is a reasonable
probability that, but for counsel’s errors, he would not
have pleaded guilty and would have insisted on going to
trial.” 474 U.S., at 59. For the reasons explained above,
that sentence prescribes the threshold showing a defend-
ant must make to establish Strickland prejudice where a
defendant has accepted a guilty plea. In Hill, the Court
concluded that the defendant had not made that showing,
so it rejected his claim. The Court did not, however, fur-
ther hold that a defendant can establish prejudice by
making that showing alone.
The majority also relies on a case that arises in a com-
pletely different context, Roe v. Flores-Ortega, 528 U.S.
470 (2000). There, the Court considered a defendant’s
claim that his attorney failed to file a notice of appeal. See
id., at 474. The Court observed that the lawyer’s failure to
file the notice of appeal “arguably led not to a judicial
proceeding of disputed reliability,” but instead to “the
Cite as: 582 U. S. ____ (2017) 7
THOMAS, J., dissenting
forfeiture of a proceeding itself.” Id., at 483. The Court
today observes that petitioner’s guilty plea meant that he
did not go to trial. Ante, at 5. Because that trial “ ‘never
took place,’ ” the Court reasons, we cannot “ ‘apply a strong
presumption of reliability’ ” to it. Ante, at 5–6 (quoting
Flores-Ortega, supra, at 482–483). And because the pre-
sumption of reliability does not apply, we may not depend
on Strickland’s statement “that ‘[a] defendant has no
entitlement to the luck of a lawless decisionmaker.’ ” Ante,
at 8 (quoting 466 U.S., at 695). This point is key to the
majority’s conclusion that petitioner would have chosen to
gamble on a trial even though he had no viable defense.
The majority’s analysis, however, is directly contrary to
Hill, which instructed a court undertaking a prejudice
analysis to apply a presumption of reliability to the hypo-
thetical trial that would have occurred had the defendant
not pleaded guilty. After explaining that a court should
engage in a predictive inquiry about the likelihood of a
defendant securing a better result at trial, the Court said:
“As we explained in Strickland v. Washington, supra,
these predictions of the outcome at a possible trial, where
necessary, should be made objectively, without regard for
the ‘idiosyncrasies of the particular decisionmaker.’ ” 474
U.S., at 59–60 (quoting 466 U.S., at 695). That quote
comes from the same paragraph in Strickland as the
discussion about the presumption of reliability that at-
taches to the trial. In other words, Hill instructs that the
prejudice inquiry must presume that the foregone trial
would have been reliable.
The majority responds that Hill made statements about
presuming a reliable trial only in “discussing how courts
should analyze ‘predictions of the outcome at a possible
trial,’ ” which “will not always be ‘necessary.’ ” Ante, at 10,
n. 3 (quoting Hill, 474 U.S., at 59–60). I agree that such
an inquiry is not always necessary—it is not necessary
where, as in Hill, the defendant cannot show at the
8 JAE LEE v. UNITED STATES
THOMAS, J., dissenting
threshold that he would have rejected his plea and chosen
to go to trial. But that caveat says nothing about the
application of the presumption of reliability when a de-
fendant can make that threshold showing.
In any event, the Court in Hill recognized that guilty
pleas are themselves generally reliable. Guilty pleas
“rarely” give rise to the “concern that unfair procedures
may have resulted in the conviction of an innocent defend-
ant.” Id., at 58 (internal quotation marks omitted). That
is because “a counseled plea of guilty is an admission of
factual guilt so reliable that, where voluntary and intelli-
gent, it quite validly removes the issue of factual guilt
from the case.” Menna v. New York, 423 U.S. 61, 62, n. 2
(1975) (per curiam) (emphasis deleted). Guilty pleas, like
completed trials, are therefore entitled to the protections
against collateral attack that the Strickland prejudice
standard affords.
Finally, the majority does not dispute that the prejudice
inquiry in Frye and Lafler focused on whether the defend-
ant established a reasonable probability of a different
outcome. The majority instead distinguishes those cases
on the ground that they involved a defendant who did not
accept a guilty plea. See ante, at 7, n. 1. According to the
majority, those cases “articulated a different way to show
prejudice, suited to the context of pleas not accepted.”
Ibid. But the Court in Frye and Lafler (and Hill, for that
matter) did not purport to establish a “different” test for
prejudice. To the contrary, the Court repeatedly stated
that it was applying the “same two-part standard” from
Strickland. Hill, supra, at 57 (emphasis added); accord,
Frye, 566, U. S., at 140 (“Hill established that claims of
ineffective assistance of counsel in the plea bargain con-
text are governed by the two-part test set forth in Strick-
land”); Lafler, 566 U.S., at 162–163 (applying Strickland).
The majority today abandons any pretense of applying
Strickland to claims of ineffective assistance of counsel
Cite as: 582 U. S. ____ (2017) 9
THOMAS, J., dissenting
that arise at the plea stage. It instead concludes that one
standard applies when a defendant goes to trial (Strick-
land); another standard applies when a defendant accepts
a plea (Hill); and yet another standard applies when
counsel does not apprise the defendant of an available plea
or when the defendant rejects a plea (Frye and Lafler).
That approach leaves little doubt that the Court has
“open[ed] a whole new field of constitutionalized criminal
procedure”—“plea-bargaining law”—despite its repeated
assurances that it has been applying the same Strickland
standard all along. Lafler, supra, at 175 (Scalia, J., dis-
senting). In my view, we should take the Court’s prece-
dents at their word and conclude that “[a]n error by coun-
sel . . . does not warrant setting aside the judgment of a
criminal proceeding if the error had no effect on the judg-
ment.” Strickland, 466, U. S., at 691.
III
Applying the ordinary Strickland standard in this case,
I do not think a defendant in petitioner’s circumstances
could show a reasonable probability that the result of his
criminal proceeding would have been different had he not
pleaded guilty. Petitioner does not dispute that he pos-
sessed large quantities of illegal drugs or that the Gov-
ernment had secured a witness who had purchased the
drugs directly from him. In light of this “overwhelming
evidence of . . . guilt,” 2014 WL 1260388, *15 (WD Tenn.,
Mar. 20, 2014), the Court of Appeals concluded that peti-
tioner had “no bona fide defense, not even a weak one,”
825 F.3d 311, 316 (CA6 2016). His only chance of suc-
ceeding would have been to “thro[w] a ‘Hail Mary’ at trial.”
Ante, at 8. As I have explained, however, the Court in
Strickland expressly foreclosed relying on the possibility of
a “Hail Mary” to establish prejudice. See supra, at 3.
Strickland made clear that the prejudice assessment
should “proceed on the assumption that the decisionmaker
10 JAE LEE v. UNITED STATES
THOMAS, J., dissenting
is reasonably, conscientiously, and impartially applying
the standards that govern the decision.” 466 U.S., at 695.
In the face of overwhelming evidence of guilt and in the
absence of a bona fide defense, a reasonable court or jury
applying the law to the facts of this case would find the
defendant guilty. There is no reasonable probability of
any other verdict. A defendant in petitioner’s shoes, there-
fore, would have suffered the same deportation conse-
quences regardless of whether he accepted a plea or went
to trial. He is thus plainly better off for having accepted
his plea: had he gone to trial, he not only would have faced
the same deportation consequences, he also likely would
have received a higher prison sentence. Finding that
petitioner has established prejudice in these circumstances
turns Strickland on its head.
IV
The Court’s decision today will have pernicious conse-
quences for the criminal justice system. This Court has
shown special solicitude for the plea process, which brings
“stability” and “certainty” to “the criminal justice system.”
Premo, 562 U.S., at 132. The Court has warned that “the
prospect of collateral challenges” threatens to undermine
these important values. Ibid. And we have explained that
“[p]rosecutors must have assurance that a plea will not be
undone years later,” lest they “forgo plea bargains that
would benefit defendants,” which would be “a result favor-
able to no one.” Id., at 125.
The Court today provides no assurance that plea deals
negotiated in good faith with guilty defendants will re-
main final. For one thing, the Court’s artificially cabined
standard for prejudice in the plea context is likely to gen-
erate a high volume of challenges to existing and future
plea agreements. Under the majority’s standard, defend-
ants bringing these challenges will bear a relatively low
burden to show prejudice. Whereas a defendant asserting
Cite as: 582 U. S. ____ (2017) 11
THOMAS, J., dissenting
an ordinary claim of ineffective assistance of counsel must
prove that the ultimate outcome of his case would have
been different, the Court today holds that a defendant who
pleaded guilty need show only that he would have rejected
his plea and gone to trial. This standard does not appear
to be particularly demanding, as even a defendant who
has only the “smallest chance of success at trial”—relying
on nothing more than a “ ‘Hail Mary’ ”—may be able to
satisfy it. Ante, at 7, 8. For another, the Court does not
limit its holding to immigration consequences. Under its
rule, so long as a defendant alleges that his counsel omit-
ted or misadvised him on a piece of information during the
plea process that he considered of “paramount im-
portance,” ante, at 10, he could allege a plausible claim of
ineffective assistance of counsel.
In addition to undermining finality, the Court’s rule will
impose significant costs on courts and prosecutors. Under
the Court’s standard, a challenge to a guilty plea will be a
highly fact-intensive, defendant-specific undertaking.
Petitioner suggests that each claim will “at least” require
a “hearing to get th[e] facts on the table.” Tr. of Oral Arg.
7. Given that more than 90 percent of criminal convictions
are the result of guilty pleas, Frye, 566 U.S., at 143, the
burden of holding evidentiary hearings on these claims
could be significant. In circumstances where a defendant
has admitted his guilt, the evidence against him is over-
whelming, and he has no bona fide defense strategy, I see
no justification for imposing these costs.
* * *
For these reasons, I would affirm the judgment of the
Court of Appeals. I respectfully dissent.