Predicting the Complex Future of Retroactivity in Massachusetts: Commonwealth v. Sylvain

by Professor Daniel Kanstroom

Case Focus

Kanstroom_Dan“[We] cannot escape the demands of judging or of making the difficult appraisals inherent in determining whether constitutional rights have been violated.”

Goldberg, J., Haynes v. Washington, 373 U.S. 503, 515 (1963)

In Commonwealth v. Sylvain,466 Mass. 422 (2013), the SJC held that the requirements placed on criminal defense lawyers to properly advise defendants about certain immigration consequences enunciated in Padilla v. Kentucky, 559 U.S. 356 (2010) are retroactive to 1997.  The SJC, relying both on the Sixth Amendment and on art. 12 of the Massachusetts Declaration of Rights, diverged from the U.S. Supreme Court on the retroactivity question.  This very important—but rather esoteric—immigration law case may have profound implications regarding the retroactivity of recent holdings in such areas as public trial rights during jury selection and juvenile sentencing.

The SJC achieved a just outcome while reminding the legal community why retroactivity is an extraordinarily difficult jurisprudential concept and why immigration law has long been known as a subject that could “cross the eyes of a Talmudic Scholar.” The daunting complexities presented by the case derived in part from certain anachronistic late nineteenth century legal doctrines establishing “plenary power” over noncitizens seeking to enter the United States as well as those facing deportation.  The Court has held that certain noncitizens seeking to enter the United States have no enforceable constitutional rights and that deportation exercised under that power was not criminal punishment.  Therefore, the specific constitutional norms attendant to the criminal justice system are largely inapplicable to deportees.  See Fong Yue Ting v. United States, 149 U.S. 698 (1893).

For more than a century, the constitutional implications of these doctrines and their progeny frequently (but not always) defeated claims of ineffective assistance of counsel by deportees who were badly advised (or not advised at all) by their criminal lawyers.  Noncitizens have the right to appointed counsel in the criminal justice system, but they do not have such a right in deportation proceedings.  Deportation has often been deemed a civil “collateral” consequence of criminal conviction.  Among other implications of this categorization, criminal defense lawyers have sometimes been found to have no professional duty to advise defendants about such consequences.

In 2010, however, the Supreme Court decided Padilla v. Kentucky, 559 U.S. 356 (2010), a case in which the question of ineffective assistance was squarely presented. Mr. Padilla, a long-term lawful permanent resident of the United States, had apparently been advised to plead guilty to a drug-related charge in criminal court, which—unbeknownst to him—virtually guaranteed his deportation and lifetime banishment from the United States and his family.  The Court upheld his claim that his criminal defense counsel was ineffective due to this incorrect advice concerning the risk of deportation. This was in many respects a path-breaking, virtually unprecedented constitutional decision, with powerful Fifth and Sixth Amendment implications. See generally, Daniel Kanstroom, The Right To Deportation Counsel in Padilla v. Kentucky: The Challenging Construction of the Fifth-And-A-Half Amendment, 58 UCLA L. REV. 1461 (2011); see also, Daniel Kanstroom Padilla v. Kentucky and the Evolving Right to Deportation Counsel: Watershed or Work-in-Progress? 45 NEW ENGLAND L. REV. 305 (2011).

The Court, most significantly, recognized that deportation as a consequence of a criminal conviction now has such a close connection to the criminal process that it is uniquely difficult to classify it as either a “direct or a collateral consequence.”  Padilla at  364.  The two systems, in short, have become inextricably linked. Further, the Court recognized that “the landscape of federal immigration law has changed dramatically.” In the past there were only a “narrow class of deportable offenses and judges wielded broad discretionary authority to prevent deportation.” But now, the regime contains a much-expanded class of deportable offenses and it has limited the authority of judges “to alleviate the harsh consequences of deportation.” Id. at 357.  As a result of these changes, the “drastic measure” of deportation or removal, . . . is now virtually inevitable for a vast number of noncitizens convicted of crimes.  Deportation has become “an integral part—indeed, sometimes the most important part—of the penalty that may be imposed on noncitizen defendants who plead guilty to specified crimes.” Id. at  362 (emphasis added).  From this logic, one can easily see why substantial due process protections, and also some of the more specific protections normally tied to the criminal justice system, are warranted. See generally Daniel Kanstroom, Deportation, Social Control, and Punishment: Some Thoughts About Why Hard Laws Make Bad Cases, 113 HARVARD LAW REVIEW 1890-1935 (June, 2000).

The question quickly arose whether the Padilla model would be retroactive.  Unfortunately, Padilla itself did not address this question.  In Commonwealth v. Clarke, 460 Mass. 30 (2011), the SJC held that Padilla was retroactive, at least as to convictions that became final after April 1, 1997 (the effective date of relevant changes to deportation law).  The SJC followed a long-standing framework derived from Teague v. Lane, 489 U.S. 288 (1989). See also, Commonwealth v. Bray, 407 Mass. 296, 300-301 (1990) (adopting Teague model).  The essential question from Teague and progeny was whether the Supreme Court in Padilla had announced a “new” rule.  A “new” rule, very simply put, “breaks new ground or imposes a new obligation” on the government.  If so, the Padilla norms would not be retroactive. In Clarke, the SJC concluded that Padilla was not a new rule because it was merely an application of well-recognized Sixth Amendment ineffective assistance of counsel standards. See Strickland v. Washington, 466 U.S. 668 (1984); Clarke at 34-46.

So far, so good; and so far, at least moderately clear.  However, things soon got murkier.  In Chaidez v. U.S., 133 S. Ct. 1103 (2013), the Supreme Court held that Padilla had in fact announced a “new” rule and therefore its holding should not be applied retroactively by federal courts.  Chaidez, however, did not necessarily bind state courts.  Indeed, the Supreme Court had recognized the propriety of such divergence in Danforth v. Minnesota, 552 U.S. 264 (2008) in which the Court held that Teague does not constrain the authority of state courts to give broader effect to “new” rules of criminal procedure.

In Sylvain, the SJC continued to view retroactivity differently from the Supreme Court.  The SJC concluded that Padilla did not announce a “new” rule for the “simple reason that it applied a general standard—designed to change according to the evolution of existing professional norms—to a specific factual situation.”  Sylvain at 435 (citing Clarke, supra at 36, 38-39, 43; Chaidez, supra at 1114-1116 (Sotomayor, J., dissenting).  Importantly, the SJC based its ruling both on the Sixth Amendment and on art. 12 of the Massachusetts Declaration of Rights.  As one excellent Practice Advisory notes, art. 12 may prove to be a broader source of rights for noncitizens than the Sixth Amendment.  See CPCS, Immigration Impact Unit, Practice Advisory on the Retroactivity of Padilla in Massachusetts: Commonwealth v. Sylvain, 466 Mass. 422 (2013), October 2013.

The SJC also correctly noted that professional standards in Massachusetts have long required criminal defense lawyers to advise noncitizen clients about immigration consequences.  Practitioners thus now face a certain dissonance in that criminal defendants prosecuted in federal courts who face or have faced deportation may only cite Padilla prospectively, while state court defendants in Massachusetts may use the Padilla ruling to seek to vacate convictions dating back to 1997.  The practical difficulties involved in bringing such claims on behalf of deportees are still significant, however. See, e.g., Perez Santana v. Holder, No. 12-2270 (1st Cir. Sept. 27, 2013) (invalidating regulation barring such claims), and Bolieiro v. Holder, No. 12-1807 (1st Cir. Sept. 27, 2013) (same).

Sylvain may also portend greater assertiveness by the SJC in certain other arenas where retroactive application of constitutional holdings is at issue.  The SJC has now made clear that it considers a “new” rule to be such only if the result is contrary to precedent.  Sylvain, at 434.  This is rather narrower than the approach taken by the Supreme Court, which has used the formulation of that which was not “apparent to all reasonable jurists.”  The SJC formulation could thus expand state court remedies for other violations of constitutional rights.  Indeed, the Court highlighted that retroactivity in Sylvain was required by “tenets of fundamental fairness.”  Sylvain at 437, citing Commonwealth v. Amirault, 424 Mass. 618, 639 (1997).  It therefore seems quite possible that Sylvain could influence such pending questions as the retroactivity of rulings about mandatory life without parole sentences for juveniles—See Diatchenko v. D.A. for the Suffolk District, SJC-11453—and public trial rights during jury selection. See Commonwealth v. Alebord, SJC-11354.  Retroactivity analysis will thus have to consider, in addition to precedent, such factors as the evolution of practice, reliance, and deeper normative questions of justice and fairness.

Daniel Kanstroom is a Professor of Law and Director of the International Human Rights Program at Boston College Law School. He is also the Founder of the Post-Deportation Human Rights Project.



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