United States v. Armendariz

Case: 22-50647 Document: 00516876397 Page: 1 Date Filed: 08/29/2023
United States Court of Appeals
for the Fifth Circuit United States Court of Appeals
Fifth Circuit
____________ FILED
August 29, 2023
No. 22-50647 Lyle W. Cayce
____________ Clerk
United States of America,
Plaintiff—Appellee,
versus
Virginia Estrada Armendariz,
Defendant—Appellant.
______________________________
Appeal from the United States District Court
for the Western District of Texas
USDC No. 3:21-CR-782-1
______________________________
Before King, Smith, and Elrod, Circuit Judges.
Jennifer Walker Elrod, Circuit Judge:
Virginia Estrada Armendariz, a lawful permanent resident of the
United States, was charged with importation of a controlled substance in
violation of 21 U.S.C. § 952(a). Her lawyer told her that if she pleaded guilty,
it was “very likely” that she would be deported. She nonetheless entered the
plea. Armendariz then learned that her offense did not just possibly make her
deportable, it automatically did so. See 8 U.S.C. § 1227(a)(2)(B)(i). She then
moved to withdraw her plea, alleging that if she had known the full scope of
the immigration consequences of her plea, she would not have entered it.
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The district court denied Armendariz’s motion and sentenced her.
Armendariz appealed.
It is deficient performance under the Sixth Amendment for a criminal
defense lawyer not to tell an alien client that his or her offense will have
immigration consequences. Padilla v. Kentucky, 559 U.S. 356, 369 (2010).
However, the kind of warning that the lawyer must provide is not entirely
settled. This case presents the following question: when an offense makes an
alien presumptively deportable, does a lawyer’s warning of “very likely”
deportation satisfy the right to effective assistance of counsel?
We hold that it does. When defense counsel tells an alien client that a
conviction will have serious immigration consequences, including “very
likely” deportation, that defendant has received sufficient advice to make an
informed plea decision, as required by the Sixth Amendment. The district
court therefore did not abuse its discretion in denying Armendariz’s motion
to withdraw her plea, and the judgment is AFFIRMED.
I
Armendariz is a 53-year-old woman who has been a legal permanent
resident of the United States since 1994. In 2021, Armendariz responded to
a Facebook advertisement offering $100 for her to drive clothes, shoes, and
cash from a store in El Paso, Texas, to a store in Juarez, Mexico. Armendariz
was suspicious that this was actually a solicitation to transport drugs, but she
“decided to go ahead with the job and take the risk due to lack of work and
needing money.” She met the job advertisers in Mexico, who outfitted her
truck with a GPS tracker and told her to drive to El Paso to pick up the
inventory that she would then bring back to Mexico.
When Armendariz attempted to cross the border and reenter Texas, a
United States Customs and Border Protection narcotics-detecting dog
alerted to the presence of drugs in Armendariz’s truck. The officers
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inspected the truck and found many bundles of marijuana hidden in the hood,
engine, front doors, back seat, and tailgate.
Armendariz was charged in the Western District of Texas with
knowingly and intentionally conspiring to import 43.9 kilograms of
marijuana. Armendariz initially pleaded not guilty.
However, Armendariz later decided to enter a guilty plea as to count
one, importation of a controlled substance in violation of 21 U.S.C. § 952(a).
Before Armendariz entered the plea, she discussed the issue of immigration
consequences at length with the magistrate judge (as required by Federal
Rule of Criminal Procedure 11). The magistrate judge told her, “Very
unfortunately, there’s immigration consequences that take place if you plead
guilty.” He then listed a litany of immigration-related ramifications,
including (1) likely deportation, (2) very likely deportation, (3) not being
allowed to stay in the United States, (4) prison time for illegal reentry after
deportation, (5) denial of U.S. citizenship, and (6) possible relief from an
immigration judge. He asked Armendariz whether she understood these
consequences and whether she had discussed them with her attorney. She
said yes to both questions.
The plea agreement, which Armendariz said she understood, also
specifically covered the “immigration consequences of conviction.” Listed
in its own bolded, underlined, and all-caps heading on the second page of the
agreement, the immigration-related portion of the plea noted, among other
things, that:
• “Defendant recognizes that pleading guilty may affect
Defendant’s immigration status if Defendant is not a citizen of
the United States”;
• “Under federal law, a broad range of criminal offenses warrant
removal from the United States, the denial or cancellation of
certain immigration benefits, and/or denaturalization,
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including the offense(s) to which Defendant has agreed to
plead guilty pursuant to this Plea Agreement”;
• “Defendant’s offense(s) of conviction presumptively
require(s) the removal of a defendant who is not a U.S.
Citizen”; and
• “Defendant nevertheless affirms that Defendant wants to
enter a plea of guilty, regardless of any immigration or
naturalization consequences that may result from the guilty
plea and even if those consequences include Defendant’s
removal from the United States or denaturalization.”
Despite receiving these warnings, Armendariz stated that she
understood the agreement and entered the plea. The district court judge
accepted it. Two months later, Armendariz’s counsel withdrew, and the
attorney that is currently representing her substituted in.
Under the advice of her new counsel, Armendariz moved to withdraw
her guilty plea. Armendariz alleged in her motion that she had not realized
when pleading guilty that she was pleading to an “aggravated felony” that
would make her automatically deportable. 8 U.S.C. § 1227(a)(2)(A)(iii).
And she argued that under Supreme Court and Fifth Circuit precedent,
“when the deportation consequence [of a guilty plea] is truly clear, . . . the
duty to give correct advice is equally clear.” United States v. Urias-Marrufo,
744 F.3d 361, 366 (5th Cir. 2014) (quoting Padilla, 559 U.S. at 369).
Armendariz said that although the lawyer representing her at the time
of the plea agreement had warned her that there would be immigration
consequences, he had not accurately characterized the gravity of those
consequences. Armendariz alleged that at the time of agreeing to the plea,
she had been under the false impression that she could at least fight to keep
her lawful permanent resident status after the criminal case resolved.
Armendariz believed this because her prior attorney had referred
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Armendariz’s daughter to an immigration lawyer, and the immigration
lawyer had told Armendariz’s daughter that she could represent Armendariz
when the criminal case was resolved.
The district court denied Armendariz’s motion to withdraw her guilty
plea. After hearing arguments, the judge announced his findings from the
bench. The judge’s full statement was:
The actual holding in Padilla says there is a duty that, in
essence—and I’m paraphrasing—there is a duty that cannot be
saved at the plea colloquy for the defendant to affirmatively
state—affirmatively state that discussions were had with
defense lawyer about the consequences of the plea of guilty.
Ms. Armendariz unequivocally stated that she had those
discussions with her lawyer. And this is not a case—reading
the transcript of the proceedings before Judge Castaneda, he
did exactly what he was supposed to do. He wasn’t saving the
case for [Armendariz’s counsel at the plea stage]. He simply
asked, This may happen, and he stated that to her. Are you
aware of that? Yes. Did you discuss that with your lawyer?
And she unequivocally said yes. That’s the Padilla duty.
So I’m finding that, based on the evidence before the
Court, that [Armendariz’s counsel] by Ms. Armendariz’ own
words informed her that there would be—that there were likely
to be—there could be immigration consequences to her plea of
guilty, and the judge simply confirmed that in his plea colloquy.
So the motion to withdraw the plea of guilty is denied.
The district court then sentenced Armendariz to three years’
probation. Armendariz timely appealed.
II
We review the denial of a motion to withdraw a guilty plea for abuse
of discretion. United States v. Urias-Marrufo, 744 F.3d 361, 364 (5th Cir.
2014). “A district court abuses its discretion if it bases its decision on an
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error of law or a clearly erroneous assessment of the evidence.” Id. (quoting
United States v. Mann, 161 F.3d 840, 860 (5th Cir. 1998)). The denial of a
motion to withdraw a guilty plea that is based on a theory of ineffective
assistance of counsel is reviewable on direct appeal, not just in collateral
proceedings. Id. at 367.
III
When negotiating a plea, a defense lawyer’s “failure to advise a lawful
permanent resident alien of likely deportation implicates the Sixth
Amendment right to effective assistance of counsel.” United States v.
Kayode, 777 F.3d 719, 723 (5th Cir. 2014) (first citing Padilla v. Kentucky, 559
U.S. 356 (2010); and then citing Strickland v. Washington, 466 U.S. 668(1984)). This Padilla violation, if proven during a motion to withdraw a guilty
plea, “compels the court to permit the defendant to withdraw the guilty
plea.” Urias-Marrufo, 744 F.3d at 369.
In absence of satisfying Padilla’s bright-line rule, a defendant may
withdraw a guilty plea if he or she “can show a fair and just reason for
requesting the withdrawal.” Fed. R. Crim. P. 11(d)(2)(B). In our circuit, this
Rule 11 standard is evaluated under a seven-factor balancing test. United
States v. Carr, 740 F.2d 339, 343–44 (5th Cir. 1984). The district court
specifically and carefully discussed these factors during the hearing on
Armendariz’s motion, and the district court did not abuse its discretion in
finding that Armendariz had not satisfied them.
A
Padilla is a gloss on Strickland’s familiar two-part standard for
evaluating claims of ineffective assistance of counsel. Under Strickland, the
court first asks whether counsel’s representation “fell below an objective
standard of reasonableness.” Strickland, 466 U.S. at 688. If so, we then ask
whether this deficiency prejudiced the defendant. Id. at 693.
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1
Padilla holds that prong one is satisfied if, during plea negotiations,
the defense lawyer does not inform the defendant “whether his plea carries
a risk of deportation.” Padilla, 559 U.S. at 374. Specifically, the Court stated
that “when the deportation consequence is truly clear, . . . the duty to give
correct advice is equally clear.” Id. at 369. Prong two is satisfied if the
defendant can demonstrate a “reasonable probability that, but for [his]
counsel’s errors, he would not have pleaded guilty and would have insisted
on going to trial.” Lee v. United States, 582 U.S. 357, 371 (2017) (alteration
in original) (quoting Hill v. Lockhart, 474 U.S. 52, 59 (1985)).
There is some ambiguity about what specific words Armendariz’s
lawyer used when explaining to her the immigration consequences of the
plea. But the district court’s factual finding—which is reviewed only for
clear error—suggests the following bottom line: Armendariz’s lawyer put her
on notice of the risk of serious immigration consequences, including
deportation. 1 The actual legal result of Armendariz’s plea is that she is
mandatorily deportable. See 8 U.S.C. § 1227(a)(2)(A)(iii); 2
_____________________
1
The district judge seemed to incorporate by reference the magistrate judge’s plea
colloquy into the factual findings made in denying the motion. But when the magistrate
judge asked in his colloquy if Armendariz had discussed “these consequences” with her
attorney, this would seem to include all of the following consequences that the magistrate
judge had listed just beforehand: (1) likely deportation, (2) very likely deportation, (3) not
being allowed to stay here, (4) prison time for illegal reentry if deported, (5) denial of U.S.
citizenship, and (6) possible relief from an immigration judge. The ambiguity between
those conflicting consequences is perhaps made starker by the fact that Armendariz
participated in the proceeding through a Spanish-language interpreter.
2
Making deportable any alien convicted of an “aggravated felony,” where that
term is defined to include “illicit trafficking in a controlled substance,” 8 U.S.C. §
1101(a)(43)(B).
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8 U.S.C. § 1227(a)(2)(B)(i). 3 This raises the question of whether the lawyer
provided Armendariz with “correct advice” about a clear immigration
consequence, as Padilla requires. Padilla, 559 U.S. at 369.
We hold that he did, for two reasons. First, even if Armendariz’s
lawyer’s advice could have been more accurate, his warning about
immigration consequences still went far and beyond what the lawyers in
Padilla and its progeny told their clients. And second, it may have been
correct for Armendariz’s counsel to say that deportation was “very likely”
as opposed to “certain.”
a
The message that Armendariz’s lawyer communicated to her,
regardless of the particular words used, was not at all like what the lawyer in
Padilla told his client. Like this case, Padilla involved a lawful permanent
resident who became deportable after pleading guilty to transporting a large
amount of marijuana. Padilla, 559 U.S. at 359 & n.1. But Padilla’s lawyer
“not only failed to advise him of this consequence prior to his entering the
plea,” the lawyer “also told him that he ‘did not have to worry about
immigration status since he had been in the country so long.’” Id. at 359(citation omitted).
The advice provided in Padilla was not just an understatement of the
consequences, as Armendariz contends was the case with her advice.
Padilla’s lawyer was flat-out wrong. Telling Padilla not to worry about his
immigration status did more than fail to put Padilla on notice. It affirmatively
misled him. By contrast, Armendariz’s lawyer at least warned her of “very
_____________________
3
Making deportable any alien convicted of a controlled-substance offense, “other
than a single offense involving possession for one’s own use of 30 grams or less of
marijuana.” 8 U.S.C. § 1227(a)(2)(B)(i).
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likely” deportation, which would not have provided Armendariz with the
same false sense of security that Padilla was given.
The Supreme Court’s most-recent examination of Padilla also shows
that Armendariz’s lawyer’s advice was different in kind from that provided
by constitutionally deficient counsel. In Lee v. United States, 582 U.S. 357(2017), a lawful permanent resident pleaded guilty to an offense that made
him automatically deportable after his lawyer told him that “the Government
would not deport him if he pleaded guilty.” Lee, 582 U.S. at 360.
Our court’s cases have held similarly. In United States v. Kayode, 777
F.3d 719 (5th Cir. 2014), a naturalized citizen pleaded guilty to a deportable
and naturalization-stripping offense because “his attorneys never warned
him prior to his sentencing hearing that he could lose his citizenship . . . and
never indicated that [he] might be deported.” Kayode, 777 F.3d at 723. And
in United States v. Urias-Marrufo, 744 F.3d 361 (5th Cir. 2014), an alien
subject to presumptive deportation after pleading guilty had discussed only
“the possible adverse immigration consequences of pleading guilty.” Urias-
Marrufo, 744 F.3d at 369; see also id. at 368 (“Urias correctly argues that,
under Padilla, she was required to be advised of the certain deportation
consequences of her plea prior to her plea hearing.”).
To summarize: The Lee lawyer gave affirmatively wrong advice (“no
deportation”). The Kayode lawyer gave no advice. And the Urias-Marrufo
lawyer gave weak or middling advice (“possible immigration
consequences”). None of those scenarios resemble the conversations that
Armendariz had with her lawyer. On the most coherent reading of the
district court’s factfinding, Armendariz’s lawyer (as well as the magistrate
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judge and the plea agreement) warned her that her deportation would be very
likely if she pleaded guilty to importing marijuana. 4
The teaching of Padilla is “how critical it is for counsel to inform her
noncitizen client that he faces a risk of deportation.” Padilla, 559 U.S. at
373–74; see also Urias-Marrufo, 744 F.3d at 369 (Garza, J., specially
concurring) (explaining why Padilla does not clearly require “counsel to
advise that deportation is a certain consequence of a guilty plea”).
Armendariz’s lawyer did more than that. He put Armendariz on notice that
she faced the “very likely” risk of deportation. If maintaining her
immigration status was dispositive in deciding whether to take the plea,
Armendariz had ample warning to inquire more about that risk.
_____________________
4
Armendariz’s lawyer also referred Armendariz to an immigration attorney. This
could give rise to the inference—though not one argued for by the United States—that
Armendariz’s lawyer satisfied his Padilla duty through delegation to a subject-matter
expert. However, we have said that the objectively reasonable assistance prong of Padilla
is concerned with “whether the defendant was informed by the defendant’s counsel” of the
relevant immigration consequences. Urias-Marrufo, 744 F.3d at 369.
Our prior holdings that immigration consequences must be relayed by the defense
lawyer him or herself comports with how Justice Alito contemporaneously interpreted the
Padilla majority opinion. Padilla, 599 U.S. at 375 (Alito, J., concurring in the judgment)
(taking the position that referrals to immigration lawyers would satisfy prong one of
Strickland, but noting that the majority opinion “nevertheless holds that a criminal defense
attorney must provide advice in this specialized area”).
And the Supreme Court has more recently noted that immigration-related
warnings that are provided by people other than the defense lawyer may be more relevant
to the second prong of the analysis (prejudice) than to the first prong (fulfillment of duty).
See Lee v. United States, 582 U.S. 357, 369 n.4 (2017) (“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.” (citing, among other cases, United States v.
Kayode, 777 F.3d 719, 728–29 (5th Cir. 2014))).
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b
The analysis in the immediately preceding section is based on the
premise that it was technically inaccurate for Armendariz’s lawyer to tell her
that removal was only “very likely,” when she would in fact be facing
presumptive deportability. That premise may not be true. After all, an
alien’s being made certainly deportable is not the same as being certainly
deported. The Seventh Circuit noted in 2016 that “not all aliens convicted of
aggravated felonies are deported.” United States v. Chezan, 829 F.3d 785,
787 (7th Cir. 2016). This is because some of them “are overlooked by
overworked immigration authorities and . . . some of them successfully plead
deferral or withholding of removal because there is a serious risk of their
being tortured or killed if returned to their country of origin.” Id. Falling
within one or more classes of deportable aliens does not categorically
eliminate the availability of asylum relief or protection under the Convention
Against Torture. See Efe v. Ashcroft, 293 F.3d 899, 903 (5th Cir. 2002).
Armendariz’s counsel could not have made a definitive statement about
Armendariz’s chances of removal without analyzing the applicability of all
other forms of relief.
The Supreme Court made a similar point this year in United States v.
Texas, 143 S. Ct. 1964 (2023). In that case, the Court held that Texas and
Louisiana lacked standing to challenge the federal government’s decision to
arrest fewer criminal noncitizens pending their removal because the
Executive Branch “retains discretion over whether to remove a noncitizen
from the United States.” Id. at 1972. And Secretary of Homeland Security
Mayorkas’s new immigration-enforcement guidelines would deprioritize
arresting people like Armendariz, who are not “suspected terrorists or
dangerous criminals, or who have unlawfully entered the country only
recently.” Id. at 1968; see also id. at 1989 (Alito, J., dissenting) (“The Court
holds Texas lacks standing to challenge a federal policy that inflicts
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substantial harm on the State and its residents by releasing illegal aliens with
criminal convictions for serious crimes.”).
Whether Armendariz’s becoming deportable would certainly lead to
her removal from the country involves not only what the relevant statutes
say. It also depends on what the Executive Branch’s current enforcement
priorities are. For a lawyer to provide his or her client an answer with 100%
certainty in the face of these shifting and hard-to-predict factors might not be
accurate. Saying merely “very likely” could be closer to the truth.
* * *
Armendariz’s lawyer provided objectively reasonable representation.
Even assuming arguendo that a warning of serious immigration consequences
and “very likely” deportation was not perfectly accurate advice, it still
performed the advocacy function that Padilla demands: putting noncitizen
clients on notice that their conviction could have an important impact on
their immigration status. And it is not clear that such advice is inaccurate,
given the complex and discretionary factors underpinning the relationship
between being deportable and being deported. Either way, Armendariz
received the effective assistance of counsel that the Sixth Amendment
guarantees her.
2
Because Armendariz received effective assistance of counsel, we do
not reach Strickland’s second prong. If there was no constitutionally
deficient performance by the attorney, then there can be no prejudice
resulting from constitutionally deficient performance.
B
Although we hold that there was no Padilla violation, we must still
review the district court’s Rule 11 analysis. Under Rule 11 of the Federal
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Rules of Criminal Procedure, “[a] defendant may withdraw a plea of guilty
. . . after the court accepts the plea, but before it imposes sentence if . . . the
defendant can show a fair and just reason for requesting the withdrawal.”
Fed. R. Crim. P. 11(d)(2)(B). This court has provided a multi-factor
balancing test for determining whether fairness and justice support granting
a defendant’s request to withdraw:
(1) whether or not the defendant has asserted his innocence;
(2) whether or not the government would suffer prejudice if the
withdrawal motion were granted; (3) whether or not the
defendant has delayed in filing his withdrawal motion; (4)
whether or not the withdrawal would substantially
inconvenience the court; (5) whether or not close assistance of
counsel was available; (6) whether or not the original plea was
knowing and voluntary; and (7) whether or not the withdrawal
would waste judicial resources . . . .
United States v. Carr, 740 F.2d 339, 343–44 (5th Cir. 1984) (footnotes
omitted).
The district court has broad discretion in evaluating these factors.
Urias-Marrufo, 744 F.3d at 364–65 (“We find at the outset that the district
court did not abuse its broad discretion with respect to its findings on the
other five factors, and we turn our attention to her critical points.”). As such,
we turn our focus to the factors that were actually disputed by the parties:
whether Armendariz received close assistance of counsel and whether the
original plea was knowing and voluntary. The district court did not abuse its
discretion in finding that both were satisfied.
As to the first factor, the “knowing and voluntary” analysis is
“inextricably tied” to the ineffective assistance of counsel claim. Id. at 365.
As such, much of the previous Padilla discussion can be imported into our
Rule 11 analysis. The district court’s careful examination of the issue was a
proper application of its discretion.
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The second factor—whether a defendant received close assistance of
counsel—requires more examination because it “is distinct” from the
effective assistance of counsel analysis under the Sixth Amendment. Id.“Counsel’s assistance may be close without being effective.” Id. at 366. We
have “previously found that close assistance of counsel was available where
counsel negotiated a plea agreement, filed motions, discussed the case with
the defendant, and explained the defendant’s rights and the weight of the
evidence.” United States v. Strother, 977 F.3d 438, 445 (5th Cir. 2020). The
same is true “where counsel was available throughout the proceedings and
the defendant expressed satisfaction with counsel.” Id.Most of these points apply here. During her plea colloquy with the
magistrate judge, Armendariz stated that her lawyer had translated the plea
agreement and explained it to her, had discussed the sentencing guidelines’
application to her case, and that she was satisfied with the assistance she had
received from her lawyer. Under this court’s precedent, that likely means
Armendariz received close assistance of counsel, even assuming arguendo
that the assistance of that counsel was ineffective as to warning of the
immigration consequences of the plea.
The district court’s detailed attention to the Rule 11 factors during the
hearing suggests that the court did not abuse its discretion in finding the
factors to be satisfied.
* * *
The district court did not abuse its discretion in denying
Armendariz’s motion to withdraw her guilty plea. First, Armendariz’s
counsel provided her with effective assistance under Padilla. Second, the
district court properly evaluated the Rule 11 factors for withdrawing a plea.
We therefore AFFIRM.
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