The Massachusetts Supreme Judicial Court is considering a critical question about criminal defense standards in Commonwealth v. Santana, a case that could impact how attorneys must advise noncitizen clients about the immigration consequences of guilty pleas. Jorge Santana, a noncitizen lawfully residing in the United States, seeks to withdraw his 2018 guilty plea to possession of a controlled substance with intent to distribute, arguing his counsel failed to inform him the plea would trigger automatic deportation. The case centers on whether Santana has made an adequate showing to warrant an evidentiary hearing on his motion to withdraw the plea based on ineffective assistance of counsel. The defendant's claims are grounded in Padilla v. Kentucky, the landmark Supreme Court decision that established defendants have a constitutional right to be informed about the immigration consequences of criminal convictions. The original charges against Santana were filed in the Salem Division of the District Court Department on June 6, 2017. After pleading guilty in 2018, Santana waited until April 21, 2022, to file his motion to withdraw the guilty plea. Judge Allen G. Swan heard the motion at the district court level. The case subsequently moved through the Massachusetts Appeals Court, which issued a decision in 2024 that is reported at 104 Mass. App. Ct. 1117. Following that appellate review, the Supreme Judicial Court granted leave for further appellate review, bringing the case before the state's highest court. The Supreme Judicial Court heard arguments in the case from September 8, 2025, through February 4, 2026, with all seven justices participating. Chief Justice Budd and Justices Gaziano, Kafker, Wendlandt, Georges, Dewar, and Wolohojian are considering the matter. Justice Wendlandt authored the court's opinion addressing the constitutional and procedural issues raised. The case involves multiple complex legal issues spanning criminal procedure, constitutional law, and immigration consequences. Key legal concepts include criminal plea procedures, the standard for effective assistance of counsel, judicial discretion in allowing plea withdrawals, and the specific obligations attorneys have when representing noncitizen defendants. The defendant is represented by Casey L. Riley, with Danya Fullerton also appearing for the defense. The Commonwealth is represented by Assistant District Attorney Jennifer D. Cohen. The case has attracted significant attention from public interest organizations, with the Committee for Public Counsel Services filing an amicus brief through attorneys Jennifer Klein, Caitlin Perry, Edward Crane, and Maria Durant. The involvement of multiple public defender organizations underscores the broader implications this case may have for criminal defense practice in Massachusetts. The timing of Santana's plea withdrawal motion raises important procedural questions. Filing the motion nearly four years after entering his guilty plea could affect his ability to successfully withdraw it, as courts generally require defendants to act promptly when seeking to undo plea agreements. However, claims of ineffective assistance of counsel, particularly those involving failure to advise about immigration consequences, may warrant different treatment under established precedent. The Padilla decision, referenced in the court's opinion, fundamentally changed how criminal defense attorneys must handle cases involving noncitizen defendants. The Supreme Court held in Padilla that defense counsel has an affirmative obligation to inform noncitizen clients about the potential immigration consequences of guilty pleas, including deportation risks. Failure to provide this advice can constitute ineffective assistance of counsel under the Sixth Amendment. For Santana, the stakes are particularly high. His guilty plea to drug distribution charges subjects him to automatic deportation under federal immigration law. Unlike some immigration consequences that require discretionary enforcement decisions, deportation for controlled substance offenses is generally mandatory, leaving little room for relief once a conviction is entered. The case highlights the intersection between state criminal law and federal immigration enforcement. As immigration enforcement has intensified in recent years, the importance of proper legal advice about immigration consequences has become increasingly critical for noncitizen defendants facing criminal charges. The Supreme Judicial Court's decision in this case will likely provide important guidance for Massachusetts criminal defense attorneys about their obligations when representing noncitizen clients. The ruling may establish new standards for what constitutes adequate advice about immigration consequences and could affect how courts evaluate motions to withdraw guilty pleas based on ineffective assistance claims. The court's decision will also address procedural questions about the standard for granting evidentiary hearings on ineffective assistance claims. This could impact how trial courts evaluate similar motions in the future and what evidence defendants must present to merit further proceedings. The case represents part of a broader national conversation about the intersection of criminal justice and immigration law, particularly regarding the rights of lawful permanent residents and other noncitizens who face severe immigration consequences for criminal convictions. The Massachusetts Supreme Judicial Court's ruling in Commonwealth v. Santana is expected to be issued in the coming months and will likely be closely watched by criminal defense attorneys, prosecutors, and immigration advocates throughout Massachusetts and beyond.