Jae Lee v. United States

(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.