                               In the

    United States Court of Appeals
                 For the Seventh Circuit
                     ____________________
No. 16-4046
UNITED STATES OF AMERICA,
                                                   Plaintiff-Appellee,
                                 v.

SERGIO MARGUERITO ZACAHUA,
                                               Defendant-Appellant.
                     ____________________

         Appeal from the United States District Court for the
           Northern District of Illinois, Eastern Division.
           No. 13-cr-576-3 — Robert M. Dow, Jr., Judge.
                     ____________________

  ARGUED SEPTEMBER 23, 2019 — DECIDED OCTOBER 8, 2019
                ____________________

   Before EASTERBROOK, HAMILTON, and ST. EVE, Circuit
Judges.
   ST. EVE, Circuit Judge. Defendant-Appellant Sergio Zaca-
hua requests that we vacate his guilty plea because the district
court failed to inform him of the potential immigration conse-
quences of his plea, as Federal Rule of Criminal Procedure
11(b)(1)(O) requires. The government concedes, and we agree,
that the district court failed to give Zacahua this admonish-
ment. But because Zacahua does not demonstrate a
2                                                   No. 16-4046

reasonable probability that, had the district court provided
this warning, he would not have pleaded guilty, we aﬃrm.
                                I
    Zacahua, a citizen of Mexico, has lived as an unauthorized
alien in the United States for over 20 years. Although he was
employed as a scrap worker and in the kitchen at Hilton ho-
tels, Zacahua also transported heroin for a drug traﬃcking or-
ganization. In 2013, Zacahua and ﬁve codefendants were in-
dicted in the United States District Court for the Northern
District of Illinois for conspiracy to distribute heroin under 21
U.S.C. §§ 841(a)(1), 846.
   On July 23, 2013, during Zacahua’s bond hearing, the gov-
ernment invoked Zacahua’s immigration status to support
their argument that he was a serious ﬂight risk. The govern-
ment explained:
       Importantly, he is admittedly an undocu-
       mented alien and a citizen of Mexico. This in-
       creases the risk of flight for this defendant be-
       cause he has significantly less ties here and
       strong ties to Mexico. Additionally, now that
       he’s arrested, even if he were not convicted, he
       faces the likelihood of removal from the United
       States to Mexico. And thus, he must surely be
       questioning why he would stay in the United
       States to face a potentially long prison term only
       to end up in Mexico at the end of the day.
In ordering Zacahua’s detention, the court highlighted his
risk of deportation: “I give some credence to the government’s
argument that Mr. Zacahua really doesn’t have any incentive
to stick around if he’s going to be deported anyway.”
No. 16-4046                                                   3

    On March 22, 2016, the district court held a change of plea
hearing pursuant to Federal Rule of Criminal Procedure 11.
The district court advised Zacahua that he faced a mandatory
minimum sentence of 120 months’ imprisonment. The district
court also informed Zacahua of the many rights he would
give up by pleading guilty and some of the potential conse-
quences of a felony conviction. But the district court never
told Zacahua that he may be removed from the United States
and denied admission in the future as a consequence of his
guilty plea, as Rule 11(b)(1)(O) requires, and neither the pros-
ecutor nor defense counsel prompted the court to make this
admonishment. After confirming Zacahua was competent to
enter a plea and that his plea was knowing and voluntary, the
district court accepted Zacahua’s guilty plea.
    On April 8, 2016, just 17 days after Zacahua pleaded
guilty, a Probation Officer interviewed Zacahua while prepar-
ing his presentence investigation report. During this inter-
view, Zacahua acknowledged his unauthorized status and
that he faced deportation. He told Probation that, when he re-
turned to Mexico, he intended to apply to work at one of the
Hilton hotels in Cabo San Lucas because of his extensive hos-
pitality experience, and that he wished to return quickly to
Mexico to care for his ailing parents.
    Zacahua’s sentencing hearing occurred on November 21,
2016. At the hearing, the district court acknowledged that
Zacahua was “likely to be eligible for deportation.” The court
discussed Mr. Zacahua’s employment prospects upon his re-
turn to Mexico: “I think if you are bilingual there are a lot of
opportunities in Mexico, actually, to be a successful person in,
really, any field where being even partially bilingual is help-
ful. … [I]t may make it easier for [you] to find and keep good
4                                                  No. 16-4046

employment in Mexico.” Later, the court stated, “I under-
stand that you’re accepting the responsibility for what you’ve
done here and you would like this to get over with as fast as
possible so you can return to Mexico.” While discussing the
§ 3553(a) sentencing factors, the court explained, “In terms of
deterrence, I think the deportation—the likely deportation—
will make it unlikely that Mr. Zacahua would have the oppor-
tunity to commit further crimes here.” As a condition of su-
pervised release, the court imposed a requirement that Zaca-
hua surrender to immigration authorities for a determination
of deportability after his release.
   Zacahua also embraced returning to Mexico as he ad-
dressed the court:
       And if I were to be deported the quickest possi-
       ble, I would go to Mexico and I will not come
       back. I have now lost everything that I had here.
       My family. So I am now going back to Mexico
       to my parents. My dad just passed away. I did
       not see him. Now, I’ve got my mom who is left
       and to take care of her.
He never raised any concern about the district court’s Rule 11
violation or his potential deportation. The district court sen-
tenced him to the mandatory minimum sentence of 120
months.
   Zacahua now wishes to withdraw his guilty plea. He
therefore appeals his conviction.
                               II
    Because Zacahua let a Rule 11 error pass without objection
in the trial court, he has forfeited this objection and must es-
tablish “plain error” to obtain relief on appeal. United States
No. 16-4046                                                      5

v. Vonn, 535 U.S. 55, 59 (2002). Under plain error review, a de-
fendant “will prevail if he can demonstrate that: (1) there was
an error; (2) the error is clear or obvious, rather than subject
to reasonable dispute; (3) the error affected [the defendant’s]
substantial rights; and (4) the error seriously affects the fair-
ness, integrity, or public reputation of judicial proceedings.”
United States v. Navarro, 817 F.3d 494, 499 (7th Cir. 2015) (citing
Puckett v. United States, 566 U.S. 129, 135 (2009)).
   To obtain relief for an unpreserved Rule 11 error, a defend-
ant “must do more than show that the Rule was technically
violated. He must show that his guilty plea was involuntary
and that he would not have entered it on the basis of the rec-
ord as a whole.” United States v. Sura, 511 F.3d 654, 660 (7th
Cir. 2007). The error must have affected the defendant’s “sub-
stantial rights,” meaning that the “defendant is obliged to
show a reasonable probability that, but for the error, he would
not have entered the plea.” United States v. Dominguez Benitez,
542 U.S. 74, 76 (2004).
    Zacahua argues that we should vacate his conviction be-
cause his guilty plea was not knowing and voluntary due to
his lack of notice regarding the immigration consequences of
his plea. Zacahua’s argument that his plea was uninformed is
entangled with his argument that the district court made a
Rule 11 error.
    Federal Rule of Criminal Procedure Rule 11(b)(1)(O) spe-
cifically requires that, before a court accepts a guilty plea, a
district court must inform the defendant that “if convicted, a
defendant who is not a United States citizen may be removed
from the United States, denied citizenship, and denied admis-
sion to the United States in the future.” This provision was
added to the rules in 2013, following the Supreme Court’s
6                                                  No. 16-4046

decision in Padilla v. Kentucky, 559 U.S. 356 (2010). FED. R.
CRIM. P. 11(b)(1)(O); Committee note to 2013 amendments. In
Padilla, the Supreme Court recognized that deportation is al-
ways “a particularly severe penalty.” Id. at 365 (internal cita-
tion omitted). “[A]s a matter of federal law, deportation is an
integral part—indeed, sometimes the most important part—
of the penalty that may be imposed on noncitizen defendants
who plead guilty.” Id. at 364. “[P]reserving 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
I.N.S. v. St. Cyr, 533 U.S. 289, 322 (2001)). Courts, however,
“should not upset a plea solely because of post hoc assertions
from a defendant about how he would have pleaded … .
Judges should instead look to contemporaneous evidence to
substantiate a defendant’s expressed preferences.” Lee v.
United States, 137 S. Ct. 1958, 1967 (2017).
    The government concedes that the district court plainly
failed to comply with Rule 11(b)(1)(O), and that Zacahua has
therefore met the first two prongs of plain error review. But
Zacahua cannot establish the third and fourth prongs of plain
error review because (1) he knew he faced a high likelihood
of deportation and (2) he cannot produce any “contempora-
neous evidence” that substantiates his post-sentencing desire
to withdraw his plea. First, at Zacahua’s bond hearing, both
the government and the court noted his immigration status
and likely deportation. Thus, Zacahua had notice of his high
risk of deportation prior to his change of plea hearing. Second,
Zacahua’s statements during his interview with his Probation
Officer—only seventeen days after entering his guilty plea—
and at his sentencing hearing demonstrated not only that he
was aware he faced deportation, but that he accepted his
eventual return to Mexico.
No. 16-4046                                                    7

   True, the evidence in the record demonstrates only that
Zacahua was on notice that he likely faced deportation as a
result of his immigration status. No evidence indicates that
Zacahua was aware that his conviction would elevate his risk
of deportation prior to entering his plea. Zacahua, however,
has failed to present any evidence that had he known of the
immigration consequences of his conviction, he would have
been reasonably likely to proceed to trial. Indeed, on this rec-
ord, his protests fall into the category of “post hoc assertions
from a defendant about how he would have pleaded” that the
Supreme Court discouraged in Lee. Lee, 137 S. Ct. at 1967.
    The Sixth Circuit case that Zacahua cites in his defense—
United States v. Ataya, 884 F.3d 318, 326 (6th Cir. 2018)—is in-
applicable to this case. In Ataya, the district court judge simi-
larly failed to inform a defendant during the plea colloquy
that he would face immigration consequences—in his case,
denaturalization—as a result of his conviction. Ataya, 884 F.3d
at 324–25. The record in Ataya, however, contained sufficient
“contemporaneous evidence in the record demonstrating a
reasonable probability that Ataya in particular would not
have pleaded guilty if he had notice of the potential adverse
immigration consequences.” Id. at 325. At sentencing, Ataya
“articulated a strong, and very reasonable, aversion to his for-
mer homeland of Syria.” Id. He explained how the ongoing
civil war had displaced his relatives. Id. He also discussed
how he is the “father of three minor children who reside in
the United States, is an active parent, and is the family’s
breadwinner.” Id. The contemporaneous concerns Ataya
voiced about returning to Syria stand in stark contrast with
Zacahua’s desire for swift release from prison so he could re-
turn to Mexico to care for his mother.
8                                                     No. 16-4046

    Similarly, the Second Circuit case that Zacahua cites—
United States v. Gonzales, 884 F.3d 457 (2d Cir. 2018) (per cu-
riam)—is readily distinguishable. Gonzales initially learned
through his PSR that he faced deportation after completing
his sentence, and the record shows that he raised the issue
with the court during his sentencing hearing after learning of
this consequence. Gonzales, 884 F.3d at 459. Because Gonzales
preserved his objection to the district court’s Rule 11 error, the
Second Circuit reviewed the record for “harmless error,” ra-
ther than plain error. Id. at 461. Therefore, unlike this case, the
burden rested with the government.
    To explain that there is a reasonable likelihood he would
have changed his sentence, Zacahua compares his situation to
that of a co-defendant, Maria Moreno. Zacahua argues that,
because Moreno also received a ten-year sentence after a jury
convicted her on all counts at trial, he would have likely taken
his chances at trial had he known of the immigration conse-
quences of his guilty plea. But this argument is flawed. First,
Moreno did not receive her sentence until November 20, 2017,
nearly a year after Zacahua entered his guilty plea, making it
impossible for him to have also considered Moreno’s sentence
when deciding whether to plead guilty. Second, even if tim-
ing were not an issue, it is impossible to tell to what extent
Moreno’s decision to proceed to trial influenced the judge’s
sentence. Moreno’s sentence is therefore irrelevant to whether
there is a reasonable probability Zacahua would have
pleaded guilty had the district court informed him of the im-
migration consequences of his guilty plea.
   We end by repeating an important note to district judges,
prosecutors, and defense counsel. Although Zacahua was un-
able to demonstrate plain error on this record, omissions like
No. 16-4046                                                      9

the one at issue in this case “are far from inconsequential and
entirely preventable.” United States v. Polak, 573 F.3d 428, 432
(7th Cir. 2009). To avoid this type of appeal in the future, we
recommend that district court judges utilize a checklist that
outlines the Rule 11 requirements at every plea colloquy they
conduct. See id. at 432–33; United States v. Stoller, 827 F.3d 591,
597 (7th Cir. 2016); United States v. Fard, 775 F.3d 939, 947 (7th
Cir. 2015); United States v. Brown, 571 F.3d 690, 695 (7th Cir.
2009).
   Critically, we again emphasize that the prosecutor and de-
fense counsel share the responsibility of ensuring the district
court complies with the requirements of Rule 11. See Polak, 573
F.3d at 432. If the court inadvertently omits a required warn-
ing during the plea colloquy, counsel should alert the court
before the court accepts the defendant’s plea. Id.
                                III
    For the foregoing reasons, we AFFIRM Zacahua’s convic-
tion and sentence.
