Mass. High Court Breathes New Life into Padilla in Commonwealth v. Sylvain

By Christopher N. Lasch

In an important decision last week the Massachusetts Supreme Judicial Court (SJC) confirmed it will continue to part ways with the United States Supreme Court over the retroactive application of the Supreme Court’s 2010 decision in Padilla v. Kentucky, 559 U.S. 356, requiring effective crimmigration counsel.

In February, the U.S. Supreme Court issued Chaidez v. United States, 133 S. Ct. 1103 (2013), holding Padilla is not to be applied retroactively. Chaidez (summarized here in February) was a disappointment on any number of levels, as was discussed extensively on this blog by Michael S. Vastine, Dawn Seibert, Rebeca Sharpless and me after its release. But last week’s decision in Commonwealth v. Sylvain, SJC-11400, slip op (Mass. September 13, 2013), in which Massachusetts held Padilla retroactive as a matter of state law, holds promise for those who hope state courts will approach Padilla retroactivity from a more sensible perspective.

Kempess Sylvain, a Haitian citizen, came to the United States with his family when he was seventeen years old, and later became a lawful permanent resident. His entire family lives in the United States and his son, parents, three sisters and long-time partner are all either United States citizens or lawful permanent residents living in the greater Boston area. Mr. Sylvain graduated from Hyde Park High School in Boston, attended Gibbs College in Boston for one year, and has worked several jobs in the area.

In October 2007 Mr. Sylvain pled guilty to possession of a controlled substance. Although Mr. Sylvain expressed concern to his lawyer about the potential immigration consequences of his guilty plea, his lawyer’s understanding was that a conviction for possession would probably not result in his deportation, and that if the negotiated sentence was less than one year, it would not be a deportable conviction. This advice was incorrect. Pursuant to § 237(a)(2)(B)(i) of the Immigration and Nationality Act which renders deportable an immigrant convicted of “any law or regulation of a State…relating to a controlled substance…other than a single offense involving possession for one’s own use of 30 grams or less of marijuana,” the conviction Mr. Sylvain acquired was a deportable offense without regard to the 11-month suspended sentence he received.

When Mr. Sylvain moved to vacate his conviction because of his lawyer’s erroneous advice, he was denied relief. While the case was pending on appeal, Chaidez was decided, and Mr. Sylvain found himself up against the U.S. Supreme Court’s antiretroactivity doctrine. The SJC accepted direct appellate review of Mr. Sylvain’s case to decide the question of Padilla’s retroactivity in the wake of Chaidez.

Sylvain is not the SJC’s first encounter with Padilla retroactivity. In its 2011 decision in Clarke v. Commonwealth, 949 N.E.2d 892 (Mass. 2011) (reviewed on this blog here), the SJC had concluded that “the reasoning and language of the Padilla decision itself” supported a conclusion that Padilla did not announce a “new rule.” Clarke, 460 Mass. at 41, 949 N.E.2d at 901. A “fair reading” of Padilla, the state’s highest court concluded, “suggests that the Justices themselves assumed that their holding would be retroactively applied.” Id. at 43, 949 N.E.2d at 903. But Clarke’s holding that Padilla was not a “new rule” for purposes of the federal antiretroactivity test (set forth in the U.S. Supreme Court’s 1989 decision in Teague v. Lane), was abrogated by Chaidez. The SJC had to decide, in Sylvain, whether Massachusetts state law would afford greater retroactivity to litigants like Kempess Sylvain.

While the SJC in Sylvain continued to find the Teague framework for determining retroactivity questions to be “sound in principle,” the SJC noted (citing Danforth v. Minnesota (2008) and state court decisions from Idaho, Alaska, and Nevada) that it was entitled to apply that framework independently and reach conclusions different from those reached by the U.S. Supreme Court. The SJC specifically departed from the Court’s conclusion in Chaidez that Padilla is a “new” constitutional rule. Adhering to its prior analysis of the question in Clarke, and siding with Justice Sotomayor’s dissent in Chaidez, the SJC held that Padilla was not new, “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.” Quoting Justice Sotomayor, the SJC noted that Padilla was driven not by changes in the Sixth Amendment, but in immigration law. Sylvain affirms once again that Padilla was fueled by the rise of crimmigration, the increased intertwining of criminal and immigration enforcement and relentless march to increase the criminal grounds for deportation and narrow the availability of relief.

The SJC specifically faulted the U.S. Supreme Court for adopting an increasingly broad definition of what constitutes a “new rule” for purposes of the Teague antiretroactivity analysis. Scholars have long raked the “new rule” analysis over the coals, and the SJC now opted to reject the Supreme Court’s jurisprudence. Thus, instead of asking whether the Padilla decision would have been “apparent to all reasonable jurists” the SJC ultimately asked whether “Massachusetts precedent at the time Padilla was decided would have dictated an outcome contrary to that in Padilla.” With this analytical move, the SJC fixed something that has been broken in Teague for a long time.

The SJC’s decision in Sylvain will encourage other states to pursue their own paths, and not “blindly follow” federal decisions on retroactivity. Sylvain could not have been more timely: The highest courts in New York, Connecticut, Tennessee, New Mexico, and Maryland have each accepted review in cases which will require those courts to decide the issue of Padilla retroactivity after Chaidez.

Christopher N. Lasch is an Assistant Professor at the University of Denver Sturm College of Law, where he co-teaches the Criminal Defense Clinic. Lasch was counsel of record and author of an amicus brief (available here) submitted on behalf of 24 Massachusetts legal academics to the Massachusetts Supreme Judicial Court in Commonwealth v. Sylvain.

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