Daynel Rodriguez-Penton v. United States

RECOMMENDED FOR FULL-TEXT PUBLICATION
Pursuant to Sixth Circuit I.O.P. 32.1(b)
File Name: 18a0221p.06
UNITED STATES COURT OF APPEALS
FOR THE SIXTH CIRCUIT
DAYNEL L. RODRIGUEZ-PENTON, ┐
Petitioner-Appellant, │
│
> No. 15-6306
v. │
│
│
UNITED STATES OF AMERICA, │
Respondent-Appellee. │
┘
Appeal from the United States District Court
for the Western District of Kentucky at Louisville.
Nos. 3:11-cr-00130-1; 3:14-cv-00547—Charles R. Simpson, III, District Judge.
Argued: May 2, 2018
Decided and Filed: October 2, 2018
Before: DAUGHTREY, STRANCH, and THAPAR, Circuit Judges.
_________________
COUNSEL
ARGUED: Doron M. Kalir, CLEVELAND-MARSHALL COLLEGE OF LAW, Cleveland,
Ohio, for Appellant. Terry M. Cushing, UNITED STATES ATTORNEY’S OFFICE, Louisville,
Kentucky, for Appellee. ON BRIEF: Doron M. Kalir, CLEVELAND-MARSHALL
COLLEGE OF LAW, Cleveland, Ohio, for Appellant. Terry M. Cushing, Candace G. Hill,
Russell M. Coleman, UNITED STATES ATTORNEY’S OFFICE, Louisville, Kentucky, for
Appellee.
STRANCH, J., delivered the opinion of the court in which DAUGHTREY, J., joined.
THAPAR, J. (pp. 11–18), delivered a separate dissenting opinion.
No. 15-6306 Rodriguez-Penton v. United States Page 2
_________________
OPINION
_________________
JANE B. STRANCH, Circuit Judge. Petitioner Daynel L. Rodriguez-Penton, a lawful
permanent resident from Cuba, appeals the district court’s denial of his motion to vacate his
sentence under 28 U.S.C. § 2255. He argues that his counsel performed deficiently by failing to
warn him of the adverse immigration consequences of pleading guilty and that he was prejudiced
by this failure. The district court denied his motion, relying on the standard for ineffective
assistance of counsel claims set forth in Hill v. Lockart, 474 U.S. 52 (1985). But the legal
landscape for such claims has changed in material ways since Hill, especially in the context of
non-citizens faced with criminal charges. Because the district court applied the wrong analytical
framework, we REVERSE and REMAND for further proceedings consistent with this opinion.
I. BACKGROUND
Rodriguez-Penton, now twenty-nine years old, moved from Cuba to the United States
with his parents when he was fifteen. He has lived in Louisville, Kentucky since his arrival and
is a permanent resident in possession of a green card. In 2011, the Government indicted
Rodriguez-Penton and his parents on a single count of conspiracy to distribute and possess
Oxycodone, a Schedule II controlled substance, in violation of 21 U.S.C. §§ 846 and
841(b)(1)(C). The Government dismissed the charges against Rodriguez-Penton’s parents
approximately six months after indictment.
Rodriguez-Penton was detained pending trial and represented by retained counsel
William M. Butler. Rodriguez-Penton cooperated with the Government at first, but eventually
stopped, in large part because he feared for his family’s safety. The Government offered
Rodriguez-Penton at least two separate plea deals in the year after his arrest, including one verbal
offer and one written offer for a six-year sentence. Rodriguez-Penton eventually moved for re-
arraignment. At the re-arraignment hearing in October 2012, he entered an open guilty plea to
the single charge in the indictment.
No. 15-6306 Rodriguez-Penton v. United States Page 3
Rodriguez-Penton’s Cuban citizenship arose at three points during the plea hearing.
First, when Rodriguez-Penton mentioned his Cuban citizenship, the district court responded that
there was no need to review the civil rights one forfeits by pleading guilty because they did not
apply to non-citizens. Second, the district court inquired whether, due to Rodriguez-Penton’s
citizenship, there would be an early sentencing. The parties answered in the negative. Third,
when asking about releasing Rodriguez-Penton from custody pending trial, the district court
asked if “there is any legal reason your client should be released from custody, or is there an
[Immigration and Customs Enforcement] detainer on him?” Butler responded “no,” although it
is not clear whether he was saying no legal reason existed or no detainer existed. At no point
during the plea hearing did the district court advise Rodriguez-Penton that pleading guilty might
have adverse immigration consequences.
In March 2013, the district court sentenced Rodriguez-Penton to a prison term of
121 months, to be followed by four years of supervised release.1 The sentencing court
mentioned that it did not know “if this conviction would result in deportation” when discussing
the supervised release portion of Rodriguez-Penton’s sentence. Rodriguez-Penton alleges that he
was unaware of the risk of deportation until after sentencing. He learned of the risk when he had
his “first appointment” with his prison counselor, who gave him “a sheet of paper where it said
that [he] could possibly be deported.”2
Rodriguez-Penton filed a direct appeal while still represented by Butler in which he
argued that his guilty plea was not knowing and voluntary because the district court failed to
advise him of the risk of deportation. He also argued that the evidence did not support the drug
1Rodriguez-Penton’s sentence was subsequently lowered to 97 months of imprisonment for reasons
unrelated to this appeal.
2The sheet of paper to which Rodriguez-Penton referred might have been the April 11, 2012, Immigration
Detainer sent by the Department of Homeland Security (DHS) to the U.S. Marshals for the Western District of
Kentucky. Although the detainer is dated April 11 and instructs that Rodriguez-Penton be notified of its existence,
the record neither confirms when it was sent to the Marshals nor indicates that Rodriguez-Penton received a copy.
The record is also silent as to whether anyone else involved in the case, including either the Assistant U.S. Attorney
or Rodriguez-Penton’s attorney, was aware of the detainer’s existence. No one mentioned the detainer even though
Rodriguez-Penton’s citizenship status arose at several points during the plea entry and sentencing hearings, and no
one mentioned it at the plea hearing in response to the district court’s specific question.
No. 15-6306 Rodriguez-Penton v. United States Page 4
quantities attributed to him at sentencing. This court rejected both arguments. United States v.
Rodriguez-Penton, 547 F. App’x 738 (6th Cir. 2013).
Rodriguez-Penton then filed a § 2255 motion to vacate, set aside, or correct his sentence.
The district court eventually appointed counsel and a magistrate judge scheduled an evidentiary
hearing where Rodriguez-Penton and Butler both testified. Butler estimated that he met with
Rodriguez-Penton fifteen times during the year between Rodriguez-Penton’s arrest and plea,
although Rodriguez-Penton said they met closer to ten times. Because Rodriguez-Penton does
not speak English, a Spanish interpreter was present during the majority of these meetings. An
interpreter was also present at all relevant hearings.
Based on the testimony and oral argument at the evidentiary hearing, the magistrate judge
issued Findings of Fact and Conclusions of Law. The magistrate judge described Butler’s
performance as follows: “[H]e merely told Rodriguez-Penton that, based on Butler’s own
experience, and what several immigration attorneys had told Butler, [Rodriguez-]Penton did not
have to worry about deportation because the Government would not return him to Cuba.” The
record confirms that Butler was not alone in reaching this conclusion—the Government also
noted that Cuban defendants are rarely subject to deportation. Yet neither Butler nor the
Government cited any authority in support of this position. The magistrate judge then noted that
“Butler conceded on cross-examination that he did not recall ever telling Rodriguez-Penton that
deportation nonetheless was a possibility.” This differed from Rodriguez-Penton’s testimony
that Butler “never discussed the subject of deportation, nor did they ever discuss the impact of
his status as a Cuban national lawfully present in the United States.”
Rather than reconcile the conflicting testimony, the magistrate judge presumed “to the
benefit of Rodriguez-Penton that attorney Butler’s performance was deficient.” He concluded
that Rodriguez-Penton’s claim of ineffective assistance of counsel failed on the prejudice prong
because Rodriguez-Penton testified unequivocally that he “would not have gone to trial, even if
he could not have negotiated a better plea arrangement than the open plea of guilty that he
previously chose to enter.” Absent a showing of prejudice, the magistrate judge held,
Rodriguez-Penton could not prevail on his § 2255 petition. The district court adopted the
No. 15-6306 Rodriguez-Penton v. United States Page 5
magistrate judge’s findings over Rodriguez-Penton’s objections, denied the § 2255 motion, and
dismissed the case with prejudice.
Rodriguez-Penton filed a timely notice of appeal and moved this court for a Certificate of
Appealability (COA). This court granted his request after finding that “Rodriguez-Penton has
arguably made a substantial showing that his attorney’s performance was deficient and that he
was actually prejudiced by counsel’s alleged error.” More specifically, the COA stated:
Rodriguez-Penton has arguably shown that, had he been advised that he could be
deported, he might have accepted a similar plea offer especially if it contained a
non-deportation clause, particularly in light of the prosecutor’s acknowledgement
that citizens of Cuba are generally not deported following a guilty plea.
Therefore, Rodriguez-Penton has made a substantial showing that counsel’s error
prejudiced him because, even though he insisted on not going to trial, the error
may have affected the outcome of the plea process.
With this background in mind, we turn to Rodriguez-Penton’s arguments on appeal.3
II. ANALYSIS
A. Standard of Review
This court reviews a district court’s denial of a § 2255 motion de novo. Short v. United
States, 471 F.3d 686, 691 (6th Cir. 2006). The reviewing court “will accept the district court’s
factual findings unless they are clearly erroneous.” McPhearson v. United States, 675 F.3d 553,
558 (6th Cir. 2012). The de novo review standard also applies to a claim of ineffective
assistance of counsel, which is a mixed question of law and fact. Id. at 559.
B. Ineffective Assistance of Counsel
The basic contours of ineffective-assistance-of-counsel claims are well defined. To
prevail on a claim that he was denied effective assistance, Rodriguez-Penton must meet the two-
part test established in Strickland v. Washington, 466 U.S. 668 (1984), and subsequently tailored
to the guilty-plea context, see Lafler v. Cooper, 566 U.S. 156, 162–63 (2012). “The performance
3After issuing the COA, this court granted the Government’s request to hold the case in abeyance pending
the Supreme Court’s decision in Lee v. United States, 137 S. Ct. 1958 (2017). The parties updated their briefs after
the decision in Lee.
No. 15-6306 Rodriguez-Penton v. United States Page 6
prong of Strickland requires a defendant to show that counsel’s representation fell below an
objective standard of reasonableness.” Id. at 163 (citation and internal quotation marks omitted).
The prejudice prong requires a defendant to show that there is a reasonable probability the
outcome of the plea process would have been different had he received competent advice. Id.Here, the district court assumed deficient performance, and rightly so. Under either
version of the facts, that of Butler or that of Rodriguez-Penton, Butler’s conduct was objectively
unreasonable. Counsel has an obligation to “advise a noncitizen client that pending criminal
charges may carry a risk of adverse immigration consequences.” Padilla v. Kentucky, 559 U.S.
356, 369 (2010) (footnote omitted). This obligation is not met if counsel either fails to mention
the risk of deportation or specifically discounts such a risk. See id. at 359, 368–69 (noting that
Padilla’s counsel told him he did “not have to worry about immigration status since he had been
in the country so long,” and finding that advice to be deficient); see also Lee v. United States,
137 S. Ct. 1958, 1964 (2017) (“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.”). We therefore agree that counsel’s performance was deficient.
The district court’s resolution of Strickland’s prejudice prong, however, requires more
attention. The prejudice inquiry asks whether there is “a reasonable probability that, but for
counsel’s unprofessional errors, the result of the proceeding would have been different.
A reasonable probability is a probability sufficient to undermine confidence in the outcome.”
Strickland, 466 U.S. at 694. In answering this inquiry in the negative, the district court relied on
Hill v. Lockhart, 474 U.S. 52 (1985), and its progeny. Hill extended Sixth Amendment
ineffective-assistance-of-counsel claims to the guilty-plea context, but held that Strickland
prejudice requires a showing of “a reasonable probability that, but for counsel’s errors, [the
defendant] would not have pleaded guilty and would have insisted on going to trial.” Id. at 59.
Recent Supreme Court authority has expanded Hill’s holding in material ways.
In Missouri v. Frye, the Supreme Court considered how to address prejudice where “[t]he
challenge [wa]s not to the advice pertaining to the plea that was accepted but rather to the course
of legal representation that preceded it with respect to other potential pleas and plea offers.”
566 U.S. 134, 141–42 (2012). Frye held that, “[t]o establish prejudice in this instance, it is
No. 15-6306 Rodriguez-Penton v. United States Page 7
necessary to show a reasonable probability that the end result of the criminal process would have
been more favorable by reason of a plea to a lesser charge or a sentence of less prison time.” Id.
at 147. Specifically distinguishing Hill, the Supreme Court explained that “Hill was correctly
decided and applies in the context in which it arose. Hill does not, however, provide the sole
means for demonstrating prejudice arising from the deficient performance of counsel during plea
negotiations.” Id. at 148. Frye thus clarified that individuals who allege ineffective assistance of
counsel during the plea process may satisfy the prejudice prong even without a showing that they
would have gone to trial were it not for counsel’s deficient performance.
Since Frye, Supreme Court authority and some persuasive caselaw from our sister
circuits have further illuminated how to demonstrate prejudice in the guilty-plea context, and
specifically as it relates to adverse immigration consequences. Lee, for example, is instructive.
Although that case, like Hill, involved a defendant who claimed that counsel’s deficient
performance deprived him of the opportunity to proceed to trial, the Supreme Court nevertheless
confirmed that a defendant may be prejudiced when his counsel’s errors deprived him of the
opportunity to make a fully informed choice during the plea process: “[W]here 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 would have affected his decisionmaking.”
137 S. Ct. at 1967 (footnote omitted). Lee therefore indicates that prejudice may lie where a
petitioner demonstrates that counsel’s deficient performance infected his decisionmaking
process, and thus undermines confidence in the outcome of the plea process. Id.
One question left open by Lee and raised by Petitioner is whether Rodriguez-Penton may
demonstrate a reasonable probability of a different outcome by showing that he would have
negotiated a plea deal that did not carry adverse immigration consequences. See id. at 1966 n.2
(“Lee also argues that he can show prejudice because, had his attorney advised him that he
would be deported if he accepted the Government’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.”). The five circuits that have addressed this question have all concluded that such
a showing would satisfy Strickland’s prejudice prong. See, e.g., United States v. Aguiar,
No. 15-6306 Rodriguez-Penton v. United States Page 8
894 F.3d 351, 362 (D.C. Cir. 2018) (remanding for an evidentiary hearing on prejudice and
noting that “[t]he Supreme Court did not suggest in Lee that a defendant must hypothesize his
counsel’s advice might be erroneous and state contemporaneously that his plea decision would
differ if that were so”); United States v. Swaby, 855 F.3d 233, 243 (4th Cir. 2017) (“Swaby has
demonstrated a reasonable likelihood that, but for his counsel’s erroneous advice, he could have
negotiated a different plea agreement. As a result, [counsel]’s deficient performance prejudiced
Swaby’s defense.”); United States v. Rodriguez-Vega, 797 F.3d 781, 788 (9th Cir. 2015)
(“A petitioner may demonstrate that there existed a reasonable probability of negotiating a better
plea by identifying cases indicating a willingness by the government to permit defendants
charged with the same or a substantially similar crime to plead guilty to a non-removable
offense.”); DeBartolo v. United States, 790 F.3d 775, 779 (7th Cir. 2015) (noting that the
petitioner “could have tried to negotiate a different plea deal for an offense that does not make
deportation mandatory”); Kovacs v. United States, 744 F.3d 44, 52 (2d Cir. 2014)
(“[A] petitioner must therefore demonstrate a reasonable probability that the prosecution would
have accepted, and the court would have approved, a deal that had no adverse effect on the
petitioner’s immigration status.”).
We find the logic of these opinions sound, and we now likewise hold that Rodriguez-
Penton may demonstrate prejudice if he can show that, had he known about the risk of adverse
immigration consequences, he would have bargained for a more favorable plea. Rodriguez-
Penton may make this showing in any number of ways, such as by showing similar plea
agreements that were reached by others charged with the same crime. See Rodriguez-Vega,
797 F.3d at 788. And, under Lee, he can still show prejudice by demonstrating that, if properly
advised, he would have gone to trial or his decisionmaking process would have been different.
137 S. Ct. at 1967. But no matter the route he takes, Rodriguez-Penton must still end up at the
same place: he must present evidence sufficient to undermine confidence in the outcome of the
plea-negotiation process. Cf. id. (cautioning against relying on “post hoc assertions” about how
a defendant would have pleaded).
Because the district court looked only to Hill, it applied an incomplete analytical
framework to Rodriguez-Penton’s prejudice arguments. For a case like this one—where a
No. 15-6306 Rodriguez-Penton v. United States Page 9
criminal defendant risks deportation by pleading guilty and his counsel fails to so advise him—
Hill does not encompass all the methods of satisfying Strickland’s prejudice prong. In light of
the legal developments since Hill and today’s holding, we think a remand for additional
proceedings is appropriate. See Rodriguez v. United States, 730 F. App’x 39, 44 (2d Cir. 2018)
(remanding to “the district court to develop a fuller record concerning the issue of prejudice”
after noting that, “[o]n the present record and under the circumstances, we cannot determine
whether Rodriguez would have opted to defend against the charges had she known she could be
denaturalized”).
The dissent incorrectly concludes that today’s opinion “announces a new right” to plea
bargaining—a right that it suggests transforms “plea bargaining into an absolute entitlement.”
(Dissenting Op. at 11, 18) To the contrary, the constitutional right at issue in this case is not
some newly minted right to plea bargaining: it is the long-recognized right to effective assistance
of counsel. And the Supreme Court has told us that the right to effective assistance extends to
the plea-bargaining process notwithstanding the fact that defendants have no constitutional right
to a plea offer. In Frye, the Court rejected both the Government’s claim that Frye “was not
deprived of any legal benefit” because “there is no right to a plea offer or a plea bargain in any
event,” and its conclusion that “any wrongful or mistaken action of counsel with respect to
earlier plea offers is beside the point.” 566 U.S. at 142. Because our criminal justice system is
effectively “a system of pleas, not a system of trials,” the Court found it “insufficient simply to
point to the guarantee of a fair trial as a backstop that inoculates any errors in the pretrial
process.” Id. at 143–44 (quoting Lafler, 566 U.S. at 170). In the context of the right to effective
assistance of counsel, Lafler concludes that it is the absence of a right to be offered a plea or to
have it accepted that is beside the point. The Court found that true because “[m]uch the same
reasoning guides cases that find criminal defendants have a right to effective assistance of
counsel in direct appeals even though the Constitution does not require States to provide a
system of appellate review at all.” Lafler, 566 U.S. at 168 (citing Evitts v. Lucey, 469 U.S. 387(1985)).
Today’s decision no more announces a right to plea bargaining than Frye or Lafler
announced such a right. In those cases, as in this one, the right at issue is the right to effective
No. 15-6306 Rodriguez-Penton v. United States Page 10
assistance of counsel at all critical stages of the criminal process. Of course, if the Government
exercises its discretion not to bargain for a guilty plea, no constitutional question is presented.
But when the Government chooses to enter into plea negotiations, the Constitution requires that
defendants receive effective assistance in navigating that crucial process. See id. (“[W]hen a
State opts to act in a field where its action has significant discretionary elements, it must
nonetheless act in accord with the dictates of the Constitution.” (quoting Evitts, 469 U.S. at
401)). And where counsel’s assistance falls short, as here, at issue is whether the defendant can
show a reasonable probability that, with proper advice, the outcome of those negotiations would
have been different. The purpose of remand is to answer that narrow question in light of the
facts of this case.
Finally, contrary to the Government’s assertions in its supplemental brief, the lack of an
obvious remedy (should Rodriguez-Penton satisfy Strickland on remand) does not automatically
equate to a failure to show prejudice. There is some analytical overlap between the two
inquiries—if there were, in fact, no other options at the time of the guilty plea, then Rodriguez-
Penton could not demonstrate a reasonable probability that the outcome would have been
different absent trial counsel’s deficient performance. But what options were available to
Rodriguez-Penton at the time of the plea is distinct from what options are available to the court
in the present day. Rodriguez-Penton has asserted that his decisionmaking process would have
been different if he had been properly advised, and the Government has not offered any
countervailing evidence that Rodriguez-Penton could not have secured a more favorable plea.
Thus, it remains possible that, on remand, he will show a reasonable probability of a different
outcome.
III. CONCLUSION
For the foregoing reasons, the district court’s decision is hereby REVERSED and
REMANDED for additional proceedings consistent with this opinion.
No. 15-6306 Rodriguez-Penton v. United States Page 11
_________________
DISSENT
_________________
THAPAR, Circuit Judge, dissenting. Being a criminal defense attorney is not easy. You
have to deal with the government, which often has the odds and resources stacked in its favor.
You have to advise a client, who may not be willing to listen. Sometimes you may have to delve
into law far afield from your day-to-day practice—like immigration law. And if you get that law
wrong and a court says you were ineffective, you may face bar sanctions.
Here, a defense attorney with a Cuban client says he sought out assistance of immigration
attorneys and advised his client that he probably would not be deported if he pled guilty. Even
the Assistant United States Attorney agreed. But things changed, and his client may get
deported. Now his client says he wishes he would have negotiated a better deal that took
deportation off the table and claims that, but for his counsel’s advice, he would have done so.
The majority agrees and in the process announces a new right—the right to negotiate more (even
though the government does not have to and has said it will not in this case).
Because this “right” is found neither in the Constitution nor the case law, I respectfully
dissent.
I.
The facts here are simple: Daynel Rodriguez-Penton, a permanent resident who came to
the United States from Cuba, pled guilty to conspiring to distribute oxycodone. He received a
sentence of 121-months imprisonment, which was later reduced to 97 months. While both the
district court and his defense attorney apparently alluded to deportation, neither specifically told
Rodriguez-Penton that he could be deported as a result of his guilty plea. R. 78, Pg. ID 248
(district court observed that “the defendant’s here on a green card,” but “d[id]n’t know if this
conviction would result in deportation”); R. 128, Pg. ID 469 (defense counsel claimed he told
Rodriguez-Penton that “since . . . he had emigrated from Cuba, I did not believe he would be
deported”). Rodriguez-Penton claims that he first learned he was deportable when he arrived at
prison. So he wanted out of his guilty plea. After an unsuccessful direct appeal in which he
No. 15-6306 Rodriguez-Penton v. United States Page 12
charged the district court with failing to inform him of the risk of deportation, United States v.
Rodriguez-Penton, 547 F. App’x 738, 740 (6th Cir. 2013), he filed this motion under 28 U.S.C.
§ 2255, claiming ineffective assistance of counsel under the Sixth Amendment.
An ineffective-assistance claim requires two showings: deficient performance and
prejudice. Strickland v. Washington, 466 U.S. 668, 687 (1984). The district court assumed that
Rodriguez-Penton’s counsel’s performance was deficient and proceeded to the prejudice
inquiry.1 But since Rodriguez-Penton claimed that, even with better advice, he would not have
forgone a plea and thus would not have proceeded to trial, the district court concluded that he
could not show prejudice. Rodriguez-Penton appeals that finding. He argues that, but for his
counsel’s immigration advice, he would have sought to negotiate a better plea offer that
promised no deportation.
II.
In recent years, the Supreme Court has decided several important cases defining the Sixth
Amendment rights of criminal defendants who plead guilty. Under those decisions, a criminal
defendant has a right to effective assistance in deciding whether to accept a plea offer. Lafler v.
Cooper, 566 U.S. 156, 168 (2012); Missouri v. Frye, 566 U.S. 134, 147 (2012). If he declines
the offer because of his lawyer’s bad advice and ends up worse off after trial, he can show
1The district court did not make any factual findings as to deficiency. See Padilla v. Kentucky, 559 U.S.
356, 359, 368–69, 374 (2010) (holding that counsel rendered constitutionally deficient performance where he told
his client that he “did not have to worry about immigration status since he had been in the country so long,” even
though the law was clear that he would be eligible to be deported). Since the district court will consider the case
again on remand, I would leave the deficiency inquiry to the district court in the first instance, rather than find
deficiency on our own. See, e.g., United States v. Williams, 527 F. App’x 457, 460 (6th Cir. 2013) (declining to
consider ineffective-assistance claim where “a variety of questions remain[ed] unresolved” and concluding that
“[t]he judge who heard the testimony and reviewed the evidence is better suited to decide these issues”); Bigelow v.
Williams, 367 F.3d 562, 576 (6th Cir. 2004). As the Supreme Court said in Padilla, “[i]mmigration law can be
complex, and it is a legal specialty of its own.” 559 U.S. at 369. When the law is not “succinct and
straightforward,” a criminal defense attorney must only advise his client that there may be a risk of “adverse
immigration consequences.” Id. And here, it appears that Rodriguez-Penton’s counsel, the Assistant United States
Attorney, and some “immigration attorneys” all believed that Rodriguez-Penton would not be deported. R. 128,
Pg. ID 484, 506. At the time, that conclusion may have been reasonable. After all, defense attorneys are not
expected to be psychic. And the United States did not normalize relations with Cuba until 2014, which likely
changed both whether the United States was willing to deport Cuban nationals and whether Cuba was willing to
accept them. These are all things that a district court would ordinarily determine before calling a defense attorney
deficient. In light of these difficult issues, it is best left to the district court to decide whether counsel’s advice rose
to the level of being “unprofessional.” Padilla, 559 U.S. at 366–67.
No. 15-6306 Rodriguez-Penton v. United States Page 13
prejudice and the court can order the prosecutor to reoffer the plea. Lafler, 566 U.S. at 168, 171.
The Court’s decision in Lee v. United States, 137 S. Ct. 1958 (2017), stands for the flip side of
the coin: if a defendant pleads guilty based on his lawyer’s bad advice but would have gone to
trial otherwise, then the defendant can show prejudice from the lost opportunity to go to trial. Id.at 1966–67.
Notwithstanding these decisions, the Supreme Court has never held that a criminal
defendant has a right to try to bargain for a plea offer he never received. So what do we do
when, as here, a defendant says he would have rolled the dice not at trial, but at more plea
negotiating? Is a defendant who loses out on the opportunity at more negotiating therefore
prejudiced because of it? Rodriguez-Penton thinks so. But neither the Constitution nor Supreme
Court precedent supports his position.
III.
Central to this case is what to make of the Court’s decision in Lee. Lee concerned a
defendant who, but for bad advice about deportation consequences, would have declined a plea
bargain and instead gone to trial—rather than seeking a better plea deal. Id. at 1966–67. In
vindicating the defendant’s lost opportunity to go to trial, Lee expressly left open the question
that we must answer. Id. at 1966 n.2 (declining to reach the argument that Lee was prejudiced
“because, had his attorney advised him that he would be deported if he accepted the
Government’s plea offer, he would have bargained for a plea deal that did not result in certain
deportation”). Still, Lee’s tea leaves are the best guidance we have to go on.
One way to read Lee is the gambler’s reading, which is to say that prejudice focuses
solely on a defendant’s lost opportunity to gamble. So long as a defendant who has pled guilty
under bad advice says that good advice would have persuaded him to roll the dice—whether at
trial or in attempting more plea negotiation—then that is prejudice. Certain portions of Lee, read
in isolation, might support that reading. Id. at 1966–67 (characterizing the prejudice inquiry as
“asking what an individual defendant would have done,” in which case “the possibility of even a
No. 15-6306 Rodriguez-Penton v. United States Page 14
highly improbable result may be pertinent to the extent it would have affected his
decisionmaking”).2
A more complete reading of Lee, however, eschews the sort of “categorical rule[]” that
would treat trials and plea negotiations the same and accounts for the Court’s repeated emphasis
on a defendant’s right to a trial. Id. at 1965–67, 1966 n.2. Where a defendant says that proper
advice would have influenced him to go to trial, courts can say that improper advice denied him
of a “proceeding” that the Sixth Amendment guarantees. Id. But the same is not true when a
defendant says that improper advice denied him the chance at negotiating a better plea. A plea
negotiation is not a “proceeding,” and a defendant has no right to it. Id.; see Weatherford v.
Bursey, 429 U.S. 545, 561 (1977) (“[T]here is no constitutional right to plea bargain; the
prosecutor need not do so if he prefers to go to trial.”); accord Frye, 566 U.S. at 148(“[A] defendant has no right to be offered a plea . . . .”). A reading of Lee that simply substitutes
“plea negotiation” for “trial” in order to require a new chance to bargain ignores that trials are a
matter of right, but plea negotiations are not.
In addition, even under the gambler’s reading of Lee, a defendant still must show a
“reasonable probability” that, but for counsel’s bad advice, he would have received a chance to
negotiate a better offer—something much more difficult in the plea-bargaining context. Lee,
137 S. Ct. at 1969 (quoting Hill v. Lockhart, 474 U.S. 52, 59 (1985)). Unless the judiciary can
force the executive to negotiate—which, for reasons discussed below, it cannot—then a chance
to negotiate is just that: a chance. It is just as (or more) likely that a defendant dead-set on
avoiding trial would be forced to settle for the exact same offer he is trying to get out of or
worse. It may never be reasonably probable (even if possible) that the government will sit down
at the negotiating table, unless the government concedes as much. And according to Rodriguez-
2Several circuits have indicated that a defendant in Rodriguez-Penton’s situation can show prejudice based
on the possibility of negotiating a better plea offer. United States v. Swaby, 855 F.3d 233, 241–43 (4th Cir. 2017);
United States v. Rodriguez-Vega, 797 F.3d 781, 788–89 (9th Cir. 2015); DeBartolo v. United States, 790 F.3d 775,
779 (7th Cir. 2015); Kovacs v. United States, 744 F.3d 44, 52–53 (2d Cir. 2014). These decisions predate Lee and
thus lack the benefit of its insights. In addition, unlike Rodriguez-Penton, the defendants in those cases pointed to
facts demonstrating that a plea offer removing the possibility of deportation was on the table (or could have been).
See, e.g., Swaby, 855 F.3d at 242–43; Rodriguez-Vega, 797 F.3d at 789; DeBartolo, 790 F.3d at 779–80; Kovacs,
744 F.3d at 53. Moreover, to the extent these cases conclude that a lost opportunity to negotiate a plea is prejudice
under Strickland, none provides a constitutionally satisfactory answer why.
No. 15-6306 Rodriguez-Penton v. United States Page 15
Penton, the government here told him in no uncertain terms that there would be no new
negotiations. Appellant Suppl. Br. 11; see also Appellee Suppl. Br. 5 (stating that a plea without
deportation is “not available to Rodriguez-Penton because he dealt in a large amount of
oxycodone, so no non-deportable crime fits the facts of this case”). So if all a defendant can
show is that he lost out on a possible chance to negotiate, that so-called prejudice cannot upset
the “strong societal interest in finality” that applies with “special force” to guilty pleas. Lee,
137 S. Ct. at 1967 (quoting United States v. Timmreck, 441 U.S. 780, 784 (1979)).
The best reading of Lee, therefore, counsels against granting Rodriguez-Penton relief.
Weatherford, 429 U.S. at 561; see Frye, 566 U.S. at 148; see also Lee, 137 S. Ct. at 1970 n.*
(Thomas, J., dissenting) (“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, and this Court has never
concluded that a defendant could show a ‘reasonable probability’ of a different result based on a
purely hypothetical plea offer subject to absolute executive discretion.” (internal citations,
quotations marks, and alteration omitted)).
Understanding that Lee did not create a new right to plea bargaining, the majority claims
that it is simply following Lafler and Frye. Majority Op. 9–10. But neither of those cases
suggest a criminal defendant can prove prejudice from missing out on hypothetical plea offers.
Indeed, the key in both Lafler and Frye was that there was a previous (more favorable) plea offer
that the defendant rejected based on bad advice. Lafler, 566 U.S. at 161, 166; Frye, 566 U.S. at
148. In Lafler, the Court stated that “[i]f no plea offer is made, or a plea deal is accepted by the
defendant but rejected by the judge, the issue raised here simply does not arise.” 566 U.S. at
168. And, in Frye, the Court held that to demonstrate prejudice, “defendants must demonstrate a
reasonable probability they would have accepted the earlier plea offer had they been afforded
effective assistance of counsel.” 566 U.S. at 147 (emphasis added). Here, Rodriguez-Penton has
no plea offer to which he can point; he simply was not offered a plea deal with a guarantee that
he would not be deported. Thus, the majority’s reliance on Lafler and Frye is misplaced.
No. 15-6306 Rodriguez-Penton v. United States Page 16
IV.
Even if Rodriguez-Penton could show prejudice, the question of remedy would present a
separate hurdle. All the possible remedies here share a common characteristic: they push the
judiciary well outside of its proper role in criminal proceedings. Ordering a prosecutor to reoffer
a plea that was already offered is problematic enough. Lafler, 566 U.S. at 183–84 (Scalia, J.,
dissenting); id. at 187–88 (Alito, J., dissenting); Williams v. Jones, 571 F.3d 1086, 1109–10
(10th Cir. 2009) (Gorsuch, J., dissenting) (explaining that this remedy “use[s] the rubric of
ineffective assistance to upend the plea bargaining process, transforming it from its historic role
as an act of executive discretion to one of judicially enforceable right”). Yet ordering the
prosecutor to extend a plea offer that was never made is something well beyond the judiciary’s
powers. See Young v. U.S. ex rel. Vuitton et Fils S.A., 481 U.S. 787, 807 (1987) (observing that
it is within a prosecutor’s discretion to decide “whether to enter into plea bargains and the terms
on which they will be established,” and that such decisions “are all made outside the supervision
of the court”). Rodriguez-Penton, to his credit, does not ask us to go that far. Instead, he
proposes that we vacate his conviction and simply recommend that the prosecutor not recharge
him.
But Rodriguez-Penton’s proposed remedy fails to solve the problem it tries to address
and creates a new problem along the way. First, the judicial branch has no business taking any
position on the exercise of prosecutorial discretion, whether “recommended” or not.
Bordenkircher v. Hayes, 434 U.S. 357, 364 (1978) (“[T]he decision whether or not to prosecute,
and what charge to file or bring before a grand jury, generally rests entirely in [the prosecutor’s]
discretion.”); see Fed. R. Crim. P. 11(c)(1) (“An attorney for the government and the defendant’s
attorney . . . may discuss and reach a plea agreement. The court must not participate in these
discussions.” (emphasis added)); United States v. Ushery, 785 F.3d 210, 219–21 (6th Cir. 2015).
And recommending that the prosecutor take an action presents a new problem: the judiciary
cannot render advisory rulings. Steel Co. v. Citizens for a Better Env’t, 523 U.S. 83, 101 (1998).
The Constitution tells us that our job as judges is to resolve “Cases” and “Controversies” through
enforceable remedies—not to write strongly-worded advice columns. U.S. Const. art. III; see
Simon v. E. Ky. Welfare Rights Org., 426 U.S. 26, 38 (1976) (observing that our jurisdiction
No. 15-6306 Rodriguez-Penton v. United States Page 17
extends only to matters where it is “likely” that an injury will be redressed by a favorable
decision). Thus, we have no power to provide the remedy Rodriguez-Penton seeks.
Rodriguez-Penton’s proposed remedy also presents a practical problem. If the court
vacates his conviction, the prosecutor may well reject the court’s recommendation of clemency
and adhere to Department of Justice policy that requires charging Rodriguez-Penton with “the
most serious, readily provable offense”—likely that to which he already pled guilty in this case.
Memorandum from the Office of the Att’y Gen. on Dep’t Charging and Sentencing Policy 1
(May 10, 2017). The government could then insist on going to trial, and Rodriguez-Penton, who
has already admitted his guilt, would likely lose. Even with credit for time served, Rodriguez-
Penton could be sentenced to more time than under his initial plea and still face the possibility of
deportation. Counsel asserts that Rodriguez-Penton has been made adequately aware of the
possible risks here, but there is no reason to expand the Sixth Amendment by judicial fiat and
push courts out of their constitutional role, only to watch Rodriguez-Penton lose a game with
long odds.
Nor is the solution to remand to the district court with the hope that more evidence and
more briefs will reveal a non-existent answer. See Majority Op. 9–10. Since courts have no
power to provide the remedy Rodriguez-Penton seeks, remanding to the district court with
instructions to sift through unavailable remedies is improper (not to mention unfair to the district
court). Williams, 571 F.3d at 1108–09. Here, there is neither prejudice nor remedy. Today’s
decision leaves to the district court the unenviable task of inventing both.3
* * *
The impact of today’s decision could be wide-reaching. Rodriguez-Penton claims that he
should have received better advice about deportation. But the decision today speaks more
broadly than immigration consequences, potentially encompassing any deficient advice that
3I recognize that the district court, which did not have the benefit of Lee, relied solely on Hill v. Lockhart in
reaching its decision. But the district court’s reliance on Hill is no reason to reverse and remand in this case. Hill
remains good law and provides the correct answer here, where the only prejudice Rodriguez-Penton can show is a
lost opportunity to go to trial, which he has made clear he does not want. 474 U.S. at 59; see Lee, 137 S. Ct. at
1965–66, 1969 (applying Hill). And again, in addition to the absence of prejudice, there is no constitutionally
available remedy the district court can provide.
No. 15-6306 Rodriguez-Penton v. United States Page 18
“infected [a defendant’s] decisionmaking process, and thus undermines confidence in the
outcome of the plea process.” Majority Op. 7. After today, any time an attorney fails to inform
a defendant about any direct consequence of a plea agreement, a defendant may have a right to
negotiate again. And so we should expect to see all manner of § 2255 motions by defendants
claiming they got bad advice about their appellate waiver, or drug quantity, or applicable
sentencing enhancements, or recommended sentencing range, to name a few. All will be
admittedly guilty, but all will want their chance at a better deal. And every one of them will
have been “prejudiced.”
It is one thing to recognize that plea bargaining is a “critical phase” of modern criminal
prosecutions. Padilla, 559 U.S. at 373. It is wholly another to transform plea bargaining into an
absolute entitlement—defendant’s satisfaction guaranteed. Since this entitlement is found
neither in the Constitution nor the case law, I respectfully dissent.