Editor’s note: Today, we post the first part of an article by Daniel Sylvester, a third-year law student at DePaul University College of Law. The second part of the article will be posted next Monday.


            It is hard today to turn on the television or read the news and not see a story discussing immigration, especially against the backdrop of the upcoming 2012 Presidential elections.  Most of the stories deal with illegal immigrants and how the states and the federal government are, or are not, dealing with that issue; however, left out of that discussion, is the fact that in the last ten years there have been over ten million new immigrants who have received lawful permanent resident (LPR) status in the United States.[1]  These LPRs have become productive, tax-paying members of society, some of whom have taken an oath to defend the Constitution of the United States of America by serving honorably in its armed forces.[2]

            In 2010, the Supreme Court decided Padilla v. Kentucky,[3] which concerned an LPR whose counsel had not advised him that pleading guilty to a felony would most likely lead to deportation, even though he had lived in the United States as an LPR for over forty years and had served honorably in the military.[4]  In what many scholars and lawyers consider a groundbreaking decision,[5] the Court ruled that the Sixth Amendment protects non-citizens by guaranteeing them effective counsel on the risks of deportation.[6]  One question that remained unanswered in that decision[7] -- does Padilla apply retroactively on collateral review?[8]  There has, as of yet, been no cohesive answer to this question, with three different Appellate Courts weighing in, creating a complex circuit split.[9]  However, in April of 2012, the Supreme Court granted certiorari in Chaidez v. United States[10]and will hear the case during its 2012-2013 term, possibly ending the circuit split by  deciding whether or not the Padilla rule applies retroactively.[11]

            This article argues that all three Appellate Courts incorrectly answered the question of retroactivity.  The correct answer is that Padilla does apply retroactively, but not as an old rule.  Padilla is actually a new rule, and it is the first rule to ever meet the watershed requirement of Teague v. Lane.[12] What does retroactive application of Padilla mean to an LPR?  It means that on habeas corpus review,[13] cases that were final before Padilla can now use the new Padilla rule and have their cases reviewed to determine whether they received ineffective counsel in making a plea agreement that affected their deportation status.[14]

            This comment will first look at the history of retroactivity in the United States.  It will track how retroactivity has changed over time and developed into today’s Teague standard.  From there, it will look at thePadilla decision by the Supreme Court, and how three Appellate Courts applied the Padilla rule under Teague.  This comment will then examine  whether Padilla is an old or new rule under Teague, and if it is a new rule determine if either of the two Teague exceptions applies to it.  To determine that, the comment will comparePadilla with the only case that, according to the Supreme Court, could have ever met the second Teagueexception, Gideon v. Wainwright.[15]  From there, it will analyze how the new Padilla rule is different from the fourteen cases that the Supreme Court has said do not apply retroactively under the second Teague exception.  Finally, this comment will argue that Padilla does apply retroactively as a new rule, since it meets the watershed requirement of the second Teague exception and then look at the impact that the application of Padilla will have on both immigration and retroactivity.

II.  Background

            While modern rules of retroactivity come from Justice Harlan’s dissents[16] in Desist v. United States[17]and Mackey v. United States,[18] a full assessment of  retroactivity requires looking at its development over time.  Retroactivity in the United States has its beginnings in early-American jurisprudence which was in turn heavily influenced by  British law.[19] Retroactivity went through a development phase from the 1950s through 1989,[20] and then came into its own in 1989 with the plurality decision in Teague.[21]

A.  An Early History of Retroactivity

            Retroactivity of court decisions is a long standing operation of American jurisprudence.[22] According to Blackstone, the purpose of a court is to interpret the law not to create new law; thus, when a court announces a legal decision, that decision applies retroactively to cases already decided since it interpreted an already existing law.[23] This complements the theory that legislatures create laws through statutes, which are prospective, and courts interpret those laws through judicial decisions, which are retroactive.[24]

            The possibility of change began building in the 1950s, though the early view of retroactive application of court decisions stayed the norm until the 1960s.[25]  In 1953, the Supreme Court decided Brown v. Allen.[26]  This decision “authorized federal courts to engage in complete relitigation [on habeas corpus] of federal claims previously adjudicated in state court criminal proceedings.”[27]  This case was followed by a series of Supreme Court decisions in the Warren Court of the 1960s that incorporated various amendments from the Bill of Rights creating a whole new series of “cognizable federal habeas petitions.”[28]  This series of activity set the stage for the Supreme Court to make changes to its view on retroactivity.[29]

B.  The Reigning in of Retroactivity

            The Supreme Court, in deciding Mapp v. Ohio,[30] fully incorporated the Fourth Amendment into the Fourteenth Amendment, holding that evidence from unconstitutional searches and seizures could not be used in state courts.[31]  This new development laid the groundwork for the first major shift in retroactivity that occurred in the Linkletter v. Walker[32]decision.  In Linkletter, the Court held that in a habeas corpus proceeding, the Mapp rule did not apply retroactively.[33]  The Court reasoned that there had been a reliance on the Court’s decisions prior to the Mapp rule and retroactive application would be a burden on the justice system.[34] The Court found no constitutional requirement that “neither prohibits nor requires retrospective effect.”[35]  The Court then formulated a case-by-case rule “weigh[ing] the merits and demerits in each case,”[36] separately by (1) the prior history of the rule being reviewed; (2) the effect and purpose the rule serves; and (3) if retroactive application of the rule would help or hinder the rule.[37]

                The Linkletter decision allowed the Court to “tailor the retroactive application of each new rule,” leading to arbitrary results based upon how fast a case moved through the system rather than whether someone was deprived of a right.[38]  This decision garnered a lot of criticism that persists still today, with Professor Paul Mishkin[39]leading the charge.[40]  Professor Mishkin stated:

When a constitutional guarantee is heightened or added to in a manner calculated to improve the reliability of a finding of guilt, the new interpretation essentially establishes a new required level of confidence as the condition for criminal punishment.  When such a new higher level is established as the current standard, there is certainly substantial justification for the position that no one shall thereafter be kept in prison of whom it has not been established by processed embodying essentially that new degree of probability that he is in fact guilty.[41]


Professor Mishkin believes the Court should focus on the reliability of the process to determine guilt or innocence under a habeas corpus review and whether or not a rule applies retroactively should be based upon this concern.[42]

            Only two years after deciding Linkletter, the Court expanded its attack on retroactivity in its Stovall v. Denno.[43]  In Stovall, the Court concluded that the rule created by two recent Supreme Court cases[44] would only apply retroactively to those two cases, and not to any cases that had already been made final, or cases that were currently in the trial or appellate process.[45]  The Court realized that denying retroactivity to both collateral review and direct review cases was unfair to “similarly situated” litigants, but saw that “as an insignificant cost for adherence to sound principles of decision making.”[46]  Additionally, Stovall adjusted the criteria that courts should use in determining whether a decision is retroactive.[47]  Post-Stovall courts were required to consider “(a) the purpose to be served by the new standards, (b) the extent of the reliance of law enforcement authorities on the old standards, and (c) the effect on the administration of justice of a retroactive application of the new standards.”[48]

C.   Justice Harlan’s Dissent

Stovall created a lot of uncertainty about retroactivity and how to apply its three-part test.[49]  Even with this uncertainty, the Supreme Court kept Stovall as the legal standard in over twenty-five cases.[50]Over the next twenty years, Stovall remained the standard though many judges defected from its ranks of supporters, the most important, if not most critical, being Justice Harlan.[51]  Just four years after the decision in Linkletter, and two years after Stovall, Justice Harlan, a part of the Stovall majority, switched sides and penned a strong dissent against affirming the Stovall three-part test in Desist.[52]

Desist decided that Katz v.United States[53] was not retroactive and reaffirmed the Stovall rule that allowed the “[c]ourt to apply a ‘new’ constitutional rule entirely prospectively.”[54]  Justice Harlan felt that Linkletter correctly decided that cases subject to direct review must have new rules of constitutional law applied to them.[55]  For cases on collateral review, Justice Harlan felt that if the rule simply expanded upon “a well-established constitutional principle” then it should apply retroactively.[56]  However, if it was a new rule, the law applied should usually be the law that was in effect at the time of the trial, unless it was a “‘new’ constitutional rule[] which significantly improve[d] the pre-existing fact-finding procedures [which] are to be retroactively applied on habeas.”[57]

Justice Harlan continued to be a voice against the Stovall test, and once again spoke strongly on that subject inMackey.[58]  There, Justice Harlan was very clear on his approach to retroactivity and his disdain of the Stovalltest, referring to it as “considerations that are appropriate enough for a legislative body.”[59]  Breaking the process down into two views, he affirmed his position in Desist that “new” rules of constitutional law should be applied to all cases on direct review.[60]  He reasoned that “simply fishing one case from the stream of appellate review . . . and then permitting a stream of similar cases . . . to flow by unaffected by that new rule constitute[s] an indefensible departure from . . . judicial review.”[61]

While Justice Harlan affirmed his position on direct review cases, he retreated somewhat on his position for cases on collateral review.[62]   His new position focused more on his view of the functions of habeas corpus than just  pure retroactive analysis.[63]  He stated that on collateral review, a new rule should not to be applied retroactively unless it meets one of two exceptions.[64]  First, if it was a new substantive due process rule which “place[d], as a matter of constitutional interpretation, certain kinds of primary, private individual conduct beyond the power of the criminal law-making authority to proscribe,” then it applied retroactively.[65]  Second, in “procedures that . . . are ‘implicit in the concept of ordered liberty.’ . . . [that] alter our understanding of the bedrock procedural elements that must be found to vitiate the fairness of a particular conviction,”[66] it would also apply retroactively.  He then pointed out that Gideon was the type of case that would meet the standards of his second exception.[67]  He felt that the Palko test, as put forth in Palko v. Connecticut,[68] provides the appropriate guidelines to determine which cases meet this second exception.[69]Palko stated specifically that the First and Sixth Amendments “ha[d] been found to be implicit in the concept of ordered liberty”[70] and thus mandated that Gideon apply retroactively.[71]

D.  GriffithTeague and the New Rules

            The Supreme Court began to accept Justice Harlan’s position in 1987 with its decision[72] in Griffith v. Kentucky.[73] In Griffith, the Court looked at the retroactive application of the Batson v. Kentucky[74] rule “that a defendant in a state criminal trial could establish a prima facie case of racial discrimination violative of theFourteenth Amendment, based on the prosecution’s use of preemptory challenges to strike members of the defendant’s race from the jury” in a direct review case.[75]  The Court adopted Justice Harlan’s view that new rules apply retroactively in direct review cases and “instruct[ed] the lower courts to apply the new rule retroactively to cases not yet final.”[76]  This case clearly represented Justice Harlan’s “fish in the stream” analogy since both Griffith and Batson had come out of the same local court with the Supreme Court decidingBatson only months before Griffith.[77]

            The full transition away from Stovall came in Teague, where a plurality opinion written by Justice O’Connor accepted most of Justice Harlan’s views on retroactivity.[78]  The Teague Court held that “the principle of habeas corpus cannot be used as a vehicle to create new constitutional rules of criminal procedure unless those rules would be applied retroactively to all defendants on collateral review through one of the two exceptions.”[79]  Justice O’Connor’s plurality opinion took the first exception directly from Justice Harlan’s dissenting opinions in Mackey and Desist.[80]  The first Teague exception for a new rule to be applied retroactively became: “if it places ‘certain kinds of primary, private individual conduct beyond the power of the criminal law-making authority to proscribe.”[81]

            The second exception that Justice Harlan espoused did not come out of Teague unscathed, but rather with some limiting modifications.[82]  Under Teague, for a new rule to meet the second exception it has to be “implicit in the concept of ordered liberty and contributed to the accuracy of the verdict.”[83]  The Teaguedecision required that the “second exception be reserved for watershed rules of criminal procedure.”[84] This watershed rule denoted a turning point, or a crucial dividing point, in criminal procedure.[85] What the Teagueruling left unanswered was the question of what constituted a new rule.  The Court answered that question in a series of three decisions that followed Teague.[86] In those decisions,[87] the Court determined that a rule is “new” under Teague when it is “not dictated by precedent.”[88]

E.  Application of Teague

            Teague has been the standard for retroactivity for twenty-two years, and not once has the Supreme Court held that the second Teague exception applies.[89]  Of the fourteen decisions from 1989 to 2009, in which the Supreme Court decided that the second Teague exception did not apply, nine were new sentencing rules;[90] one was a new police interrogations rule;[91] one was a new rule on jury instructions for a mental state element;[92] one was a new right to appeal rule;[93] one was a new confrontation clause rule;[94] andTeague itself was a new jury selection rule.[95]

            In all fourteen cases, the requirement that the rule meet Justice Harlan’s watershed standard of Gideonfor the second Teague exception was upheld by the Supreme Court.[96] For example, in Whorton, a confrontation clause case, the court did not allow the father to confront his step-daughter who accused him of sexual molestation but let the mother and police officer testify as to what the daughter had said.[97]  The Supreme Court noted that even though this was a Sixth Amendment case, “the question [to ask] is whether the new rule remedied ‘an impermissibly large risk’ of an inaccurate conviction” and in this case it did not.[98]  The Supreme Court went on to explicitly state that Gideon was the only case it had ever identified that could fit the second Teague exception.[99]  The Supreme Court believed that Gideon eliminated the intolerably high risk that a verdict would be wrong when an indigent defendant was denied representation.[100]

F.  The 2010 Padilla Decision

            In 2010, Padilla v. Kentucky, [101]  a case of an immigrant facing deportation after pleading guilty to a drug felony, came before the Supreme Court.[102]  Padilla claimed that he received ineffective counsel who had advised him to plead guilty since it would not affect his immigration status.[103]  Padilla, an LPR for forty years and an honorably discharged United States Army veteran, now faced deportation for his felony drug conviction.[104]

            The Court recognized Padilla as a unique case because of the severity of the penalty—deportation.[105]It held that “counsel must inform her client whether his plea carries a risk of deportation.  Our longstanding Sixth Amendment precedents, the seriousness of deportation as a consequence of a criminal plea, and the concomitant impact of deportation on families living lawfully in this country demands no less.”[106]  The Court reasoned that deportation constitutes a particularly severe penalty because of its connection to the criminal process, so that “advice regarding deportation is not categorically removed from the ambit of the Sixth Amendment right to counsel.”[107]  The court continued that “[p]reserving the client’s right to remain in the United States may be more important than any potential jail sentence” and that when the consequence is clear, counsel has a duty to provide his client with the correct advice.[108]  Finally, the Court noted it had “long recognized that the negotiation of a plea bargain is a critical phase of litigation for purposes of the Sixth Amendment right to effective counsel.”[109]  In that statement itself, the Supreme Court referred to the two things that make Gideon a watershed case: the “required observance of procedures implicit in the concept of ordered liberty[, such as the Sixth Amendment,] and contributed to the accuracy of the verdict.”[110]

G.  The Circuit Split on The Application of Padilla

            The lower courts have been extremely active since the Padilla decision, with three of the circuit courts rendering decisions on its application.[111]  Their decisions, instead of providing clear guidance, actually muddied the waters with three differing interpretations of Padilla.[112]

1.  The Third Circuit

            The Third Circuit became the first circuit to review a case based upon Padilla in United States v. Orocio.[113]  The court held that Padilla extended an “old” rule—Strickland[114]—and applied retroactively under collateral review.[115]

            In its Teague analysis of Padilla, the court reasoned that a “plea agreement’s immigration consequences” comes within the duties required of counsel under Strickland.[116]  It further reasoned that “every Stricklandclaim requires a fact-specific inquiry, but it [wa]s not the case that every Strickland ruling on new facts requires the announcement of a ‘new rule.’”[117]It concluded that the application of Strickland in each separate factual scenario was a “new application of an ‘old rule’ in a manner dictated by precedent.”[118]

2.  The Seventh Circuit

            Less than two months after the Third Circuit decided Orocio, the Seventh Circuit announced a completely different conclusion in Chaidez v. United States.[119]  The court held that Padilla created a new rule and never considered the question of an exception since the parties agreed neither exception applied.[120]

            The Seventh Circuit looked at the Teague definition of a new rule to determine if Padilla was following already established precedent.[121]  The court followed “the [Supreme] Court’s retroactivity jurisprudence guidance” and determined that the Supreme Court’s split with a concurrence by two justices and a dissent by two other justices met the definition of a new rule.[122]  Finally, the Seventh Circuit looked at rulings prior toPadilla and found that lower courts had consistently ruled against Padilla-type cases, thus making the Supreme Court’s decision in Padilla a new rule since the lower courts could not have predicted it.[123]

3.  The Tenth Circuit

            Only a week after the Seventh Circuit’s decision, the Tenth Circuit added its voice to the conversation by performing a full Teague analysis, addressing both exceptions, in its interpretation of Padilla in United States v. Hong.[124]

            In its analysis as to whether Padilla was an old or a new rule, the Tenth Circuit followed the same process as the Seventh Circuit and found that “Padilla announced a new rule of constitutional law.”[125] The court foundPadilla to be a new rule, then went on to determine whether either of the two Teague exceptions applied.[126]  The court determined that the rule in Padilla was procedural and not substantive, so only the second Teagueexception could apply.[127]  In looking at the second Teague exception, the court held Padilla up to the standard of Gideon and found that Padilla was not “a watershed rule of criminal procedure and does not fall within Teague’s second exception.”[128]  Finally, the Tenth Circuit determined that the Supreme Court’s discussion on “collateral attacks on guilty pleas” did not amount to the Court implying that Padilla applied retroactively.[129]