Supreme Court Denies Retroactivity of Post-Conviction Relief Claims of Immigrants Claiming Ineffective Assistance of Counsel: Padilla is not Retroactive[i]

by Jean Pierre Espinoza and Paul Palacios

A Lawful Permanent Resident (LPR) of the United States for over 26 years, that has been married for over twenty years to a U.S. citizen and has six U.S. citizen children, is suddenly facing removal proceedings. He owns his own business that employs almost twenty people and has managed to make a decent living to provide for him and his growing family. About fifteen years ago, he had some friends that were of questionable character. He ended up in the wrong place at the wrong time and with the wrong people. As a result, he was charged with possession of cocaine with intent to distribute. Although he has never even had a parking ticket before and he had a good case for an entrapment defense, his case was handled by an over-worked public defender that preferred to plead out this case. The LPR was concerned that he may lose his case and do time in jail. The last thing he wanted was to be away from his family. His public defender negotiated a deal for probation and an adjudication withheld order.

As most fearful immigrants, at the plea colloquy the LPR glossed over the question that mentions that if he is not a U.S. citizen, this conviction may subject him to deportation proceedings. The public defender informed him that he received a good deal because adjudication was withheld. All the LPR understood was that he did not have to go to jail. The public defender recommended that he plea "nolo contendere". He explained the LPR that immigration would look favorably on the judge's order granting withhold of adjudication and likely will not seek to deport him. However, the public defender was fatally wrong. As a result of this plea, the LPR became removable and his immigration lawyer might not have any relief in order to defend him in the removal proceedings.

Deportable Aliens

Under the Immigration and Nationality Act (INA), an alien is deportable if he or she committed an aggravated felony[ii]. What constitutes an aggravated felony for immigration purposes is enumerated in the Act[iii]. Offenses that can result in incarceration of one year or more of a controlled substance offense are both considered an aggravated felony for immigration purposes. An alien that has been a lawful permanent resident for at least five years and has been in the U.S. continuously for seven years or more pursuant to a legal entry into the country could apply for relief in the form of cancellation of removal before the Immigration Court[iv]. This same provision; however, bars an alien from this relief if he or she has been convicted of an aggravated felony[v].

An additional defense for avoiding deportation or removal could be to seek Adjustment of Status (also known as re-adjustment of status) based on an immigration petition from an immediate relative who is a U.S. citizen. In other words, he could have his wife or one of his children (if over 21 years old) petition for him to become a lawful permanent resident once again as a defense to deportation[vi]. That provision, however, requires that an alien be "admissible" or file a waiver of inadmissibility in order to obtain residency[vii]. This provision contains no possibility of a waiver for a controlled substance offense unless it is simple possession of marijuana of 30 grams or less[viii].

The LPR would never have pled guilty or no contest to these charges if he would have been informed that removal and banishment from his family for life would be a consequence of this plea. The LPR's only hope for stopping removal now rests with a motion to vacate his conviction based on a claim of ineffective assistance of counsel and violation of his Sixth Amendment right. His argument rests in that his criminal defense attorney failed to advise him that pleading nolo contendere to a controlled substance offense and an aggravated felony would subject him to removal with no possibility of relief under current immigration law. While this may seem like a collateral consequence, the Supreme Court of the United States stated otherwise. In Padilla v. Kentucky, the U.S. Supreme Court stated that the harsh consequence of deportation "is an integral part-indeed, some- times the most important part-of the penalty that may be imposed on noncitizen defendants who plead guilty to specified crimes".[ix]

The Problem of Retroactivity in the Application of Padilla

In its decision in Padilla, in March of 2010, the U.S. Supreme Court reached the conclusion that failure to advise a criminal defendant of the certain consequences of a criminal conviction "is not categorically removed from the ambit of the Sixth Amendment right to counsel" and therefore Strickland applies.[x] However, the Supreme Court left unresolved the question of whether this decision announced a new rule of constitutional law or simply a new application of an already existing rule. This unresolved question became critical as it would determine whether defendants whose convictions became final prior to the Padilla decision would be entitled to challenge their conviction based on ineffective assistance of counsel. If it is determined that this is indeed a new application of an old rule to a different set of facts, a defendant may attack the conviction on collateral review such as a petition for coram nobis.[xi] Under the Teague analysis, a case announces a new rule if the result was not dictated by precedent existing at the time a defendant's conviction became final.[xii] This holding is not so dictated if it would have been apparent to all reasonable jurists.[xiii] A case does not announce a new rule if it is simply an application of the principle that governed a prior decision to a different set of facts.[xiv] When the Court announces a "new rule", a person whose conviction became final before the decision may not benefit from the decision in a habeas or similar proceeding.[xv]

The Decision by the U.S. Supreme Court in Chaidez

In 2004, Roselda Chaidez pled guilty to two counts of mail fraud in the District Court for the Northern District of Illinois. She was sentenced to four years in probation. Chaidez had played a minor role in an insurance fraud scheme for which $26,000 were fraudulently collected. Chaidez personally received $1,200 for her role. Chaidez was born in Mexico and entered the United States in 1970. She became a lawful permanent resident (LPR) of the U.S. in 1977. At the time of her conviction in 2004, she had been a LPR for over 25 years.

In 2007, Chaidez applied to become a U.S. citizen and disclosed her conviction as part of the application process. This is when she discovered that under current immigration law, her conviction was considered an "aggravated felony" because the total amount of loss to the victim was over $10,000.[xvi] In fact, an applicant for naturalization is inelligible for U.S. citizenship by virtue of an aggravated felony conviction because it permanently bars an applicant from establishing good moral character.[xvii] But most importantly, a LPR convicted of an aggravated felony at any time is deemed deportable from the U.S.[xviii] Therefore, after learning of the aggravated felony conviction in her application for naturalization, the government placed Chaidez in deportation proceedings in 2009. Given that immigration law bars a LPR from applying for Cancellation of Removal as a relief from deportation if the LPR has been convicted of an aggravated felony,[xix] the consequence of Chaidez' plea was certain to result in her removal from the U.S.

Upon learning this, in early 2010, Chaidez filed a petition to vacate her 2004 conviction with the Federal District Court. While Chaidez' petition was pending, the U.S. Supreme Court issued its decision in Padilla in March of 2010. The District Court found that Chaidez could avail herself of the decision in Padilla and ruled that her criminal attorney's conduct fell below the reasonable standard expected and she was prejudiced as a result.[xx] The District Court found that under Teague, Padilla did not announce a new rule and thus Chaidez could benefit from it on collateral review.[xxi] The Court vacated Chaidez' conviction.

The Government appealed and the U.S. Court of Appeals for the Seventh Circuit reversed holding that Padilla had a declared a new rule and so should not apply in collateral review for a conviction that became final before the Padilla decision was issued on March 30, 2010.[xxii] In 2012, the U.S. Supreme Court granted certiorari to resolve the split among federal and state courts on whether Padilla applies retroactively.[xxiii]

The test in Strickland involves whether the conduct of an attorney falls below an objective standard of reasonableness as indicated by prevailing professional norms and whether a defendant suffered prejudice as a result.[xxiv] But the Court, in the majority opinion, reasoned that before deciding that question, they should analyze whether deportation advice was categorically removed from Sixth Amendment right to counsel because deportation is a collateral consequence of a criminal conviction. The Court considered whether Strickland applies at all rather than how Strickland applies. The answer of "yes" required a new rule, argued the Court. The Court reasoned that previous cases had not resolved the issue of whether advice on collateral consequences of criminal convictions violates the Sixth Amendment. The issue was left to state and lower federal courts and they almost unanimously concluded that the answer was "no".

The Court reasoned that when it decided Padilla, it answered a question about the Sixth Amendment's reach in a way that altered the law of most jurisdictions. The Court reasoned in Padilla that deportation is unique and it is a particularly severe penalty intimately related to the criminal process.[xxv] Deportation is nearly an automatic result of some convictions. The Court noted that no decision of the U.S. Supreme Court committed the Court to apply a distinction between direct and collateral consequences to define the scope of the Sixth Amendment right to counsel. The Court reasoned that the direct-versus-collateral distinction is ill-suited to Padilla. Therefore, Padillaremoved the collateral distinction and thus ruled that when a criminal lawyer gives deficient advice or fails to give advice when the immigration consequences are clear, it constitutes ineffective assistance of counsel.[xxvi]

Thus the Court in its majority opinion reasoned that "Padillahad to develop new law, establishing that the Sixth Amendment applied at all, before it could assess the performance of Padilla's lawyer under Strickland."[xxvii] In so deciding, the Court established that persons whose convictions became final before the Padilladecision cannot benefit from that ruling under collateral review. In other words, Padilla is not retroactive to cases whose convictions became final before March 30, 2010.

The Decisions by the Florida Supreme Court in Hernandez, Castano, and Diaz

On November 21, 2012, the Florida Supreme Court decided a trilogy of cases involving state convictions that became final before the Padilla decision was published.[xviii] All three cases involved motions for post-conviction relief under Florida Rule of Criminal Procedure.[xxix] Although the Florida Supreme Court took up the issue of the retroactivity of Padilla, the Court did not wait for the Chaidez decision before issuing its rulings. These decisions had two primary holdings. First, the Court ruled that the generic judicial warning that deportation "may" result from a pleas does not cure any prejudice suffered by a defendant as a result of counsel's deficient performance in cases where deportation is "presumptively mandatory".[xxx] This is the judicial warning at the plea colloquy mandated by FRCP.[xxxi] Second, the Court ruled that Padillaestablished a "new rule" and therefore it does not apply retroactively. But the Court at the same time carved out an exception for the petitioner in Castano.

Although Teague remains relevant because it sets a floor regarding retroactivity, Florida uses its own standard.[xxxii] The Court in this trilogy of cases simply stated that Padilla announced a new rule and held that it does not apply retroactively. In light of the recent decision in Chaidez, it appears the Court left the analysis to the U.S. Supreme Court and simply proceeded from that point.

The Florida Supreme Court, however, carved out an exception to the holding that Padilla does not apply retroactively to claims of post-conviction relief when convictions became final before Padilla. The Court held in its narrow exception that when a timely-filed post-conviction motion is pending as of the announcement of the Padilla decision in March of 2010, Padilla does apply in such cases.[xxxiii] Therefore this exception applies to any post-convictions motions timely-filed before Padilla and whose cases are still pending.

Both defendants in Hernandez and Diaz filed untimely petitions for post conviction relief. The Court declined to address their arguments contending that the two-year clock should be restarted based on fairness. This was curious given the fact the Court carved out the exception based on the timeliness of the post-conviction motions such as Castano.

With the decision in Chaidez, the U.S. Supreme Court has upheld the decisions of the Florida Supreme Court. Therefore, Padilla is a new rule that applies in post-conviction motions in Florida that are timely-filed in accordance with FRCP 3.850 for convictions that became final after March 30, 2010. The motion must be filed within two years after the judgment and sentence becomes final or it will be dismissed as untimely despite Padilla.


As a consequence of the decisions from the U.S. Supreme Court in Chaidez and the Florida Supreme Court our in Hernandez, Castano, and Diaz the Lawful Permanent Resident that pled guilty to possession of cocaine with intent to distribute because he was not advised of the immigration consequences of his plead by his criminal lawyer will not be able to pursue relief in the form of post-conviction relief because Padilla is not retroactive.

Unfortunately, the immigration judges do not have discretion to avoid the removal of the Lawful Permanent Resident. In cases like this, related to aggravated felonies, immigration judges do not have individual decision making.[xxxiv]

We disagree with the holding of the Supreme Court in Chaidez holding that Padilla announced a "new" rule within the meaning of Teague. Padilla does not create a new rule because it applies the existing rule in Strickland. In her dissenting opinion, Justice Sotomayor expresses that Padilla was not the drastic change in the law that the majority suggested since for years before lawyers had known that they should advise their immigrant clients of the deportation consequences of pleading guilty to a crime.[xxxv]

The constitutional right recognized in Padilla was of a fair procedure in criminal cases.[xxxvi] Not providing legal advice of the immigration consequences of a guilty plea is certainly ineffective assistance of counsel. Criminal lawyers have a duty to their clients not only for avoiding jail time, probation or criminal records; but also for avoiding their removal. Ruling that Padilla is not retroactive is unfortunate for all those persons that pled guilty under ineffective assistance in the past. In many cases, being able to vacate their convictions was the last recourse under current immigration law in order to avoid a final order of removal.

In order to avoid prejudice to their clients and violations of the Sixth Amendment right to effective assistance of counsel, practicing criminal attorneys need to be aware how a plea from a client that is not a U.S. citizen would affect his or her immigration status. Pleading guilty, no contest, or even admitting certain facts in a pre-trial intervention program enrollment can have negative effects on a client's immigration case and may result in banishment from the U.S. for life. At the very least, a criminal attorney should consult with a competent immigration attorney in such cases in order to fulfill their duty of effective assistance of counsel for clients that are not U.S. citizens.

ii INA §237(a)(2)(A)(iii); 8 U.S.C. §1227(a)(2)(A)(iii).
iii INA §101(a)(43); 8 U.S.C. §1101(a)(43).
iv INA §240A(a); 8 U.S.C. §1229a(a).
v Id.
vi INA §245(a); 8 U.S.C. §1255(a).
vii INA §212(h); 8 U.S.C. §1182(h).
viii Id.
ixPadilla v. Kentucky, 130 S. Ct. 1473 (2010).
xStrickland v. Washington, 466 U.S. 668 (1984).
xiThis applies to persons who have already been convicted of a crime and have served their sentence.
xiiTeague v. Lane, 489 U.S. 288 (1989).
xiiiLambrix v. Singletary, 520 U.S. 518, 527-528 (1997).
xivTeague, 489 U.S. at 307.
xvId. at 311.
xvi8 U.S.C. §1101(a)(43)(M)(i); INA §101(a)(43)(M)(i).
xvii8 CFR 316.10(b)(1)(ii).
xviii8 U.S.C. §1227(a)(2)(A)(iii); INA §237(a)(2)(A)(iii).
xix8 U.S.C. §1229b(a)(3); INA §240A(a)(3).
xxU.S. v. Chaidez, 730 F.Supp. 2d 896 (ND Ill. 2010).
xxiId at 904.
xxiiChaidez v. U.S., 655 F.3d 684 (CA7 2011).
xxiiiChaidez v. United States, 568 U.S. ____ (2013).
xxivStrickland Supra note 10.
xxvThe Judiciary has recognized consistently in the past that deportation is a drastic sanction which can destroy families and deprive them of liberty. See Jean Pierre Espinoza, Ineffective Assistance of Counsel in Removal Proceedings: Matter of Compean and the Fundamental Fairness Doctrine 22 Fla. J. Int'l L. 65, 70-71 (2010).
xxviChaidez Supra note 12 at 12.
xxviiiHernandez v. State, Nos. SC11-941, SC11-1357 (Fla. Nov. 21, 2012); Castano v. State, No. SC11-1571, (Fla. Nov. 21, 2012); Diaz v. State, No. SC11-1281, (Fla. Nov. 21, 2012).
xxixFRCP §3.850.
xxxHernandez Supra note 28.
xxxiFRCP §3.172(b)(8).
xxxiiWitt v. State, 387 So. 2d 922 (Fla. 1980).
xxxiiiCastano Supra note at 1-2.
xxxivSee Maritza I. Reyes, Constitutionalizing Immigration Law: The Vital Role of Judicial Discretion in the Removal of Lawful Permanent Residents, Temple L. Rev. 637, 663 (2012).
xxxvChaidez Supra note 12 at 19-30.
xxxviSee Stephen H. Legomsky, Transporting Padilla to Deportation Proceedings: A Due Process Right to the Effective Assistance of Counsel, St. Louis Univ. Public L. Rev. 43, 58 (2012).

About The Author

iJean Pierre Espinoza is an immigration lawyer at Espinoza Law Offices P.A. He graduated with an LL.M from University of Florida's Levin College of Law and with a J.D. from Stetson University College of Law.

Paul Palacios is an immigration lawyer at Palacios Law Offices P.A. He graduated with a J.D. from Stetson University College of Law. Both authors practice immigration law and immigration litigation in central Florida. They are members of the American Immigration Lawyers Association.

The opinions expressed in this article are those of the author(s) alone and should not be imputed to ILW.COM.