by David M. Reutter

The Supreme Judicial Court of Massachusetts held that a motion judge abused his discretion by denying an evidentiary hearing on a defendant’s motion to withdraw his guilty plea based on ineffective assistance of counsel. The defendant, a lawful permanent resident facing virtually mandatory removal following his drug conviction, submitted affidavits from himself and plea counsel averring that counsel failed to advise him of the virtually mandatory nature of his deportation.

The motion judge, who had also presided over the plea colloquy, discredited plea counsel’s affidavit on the ground that it contradicted counsel’s representation during the colloquy that he had discussed immigration consequences with his client pursuant to Commonwealth v. Clarke, 949 N.E.2d 892 (2011). The Court disagreed, reasoning that counsel’s colloquy statement and his subsequent affidavit were not inherently irreconcilable because Clarke itself used varied formulations when describing the required immigration advice, and it was not until Commonwealth v. DeJesus, 9 N.E.3d 789 (2014), that the Supreme Judicial Court clarified the precise obligation where deportation is virtually certain.

Background

In June 2017, a Danvers police officer observed the defendant, Jorge Santana, exchange items with a known heroin user in a supermarket parking lot. After following and stopping the defendant’s vehicle, officers observed him attempting to swallow something. Upon inspection, they discovered plastic baggies containing a tan powder consistent with heroin in his mouth. A subsequent search revealed cash and paraphernalia associated with drug distribution.

The defendant was charged with possession of a class A controlled substance with intent to distribute under G. L. c. 94C, § 32(a). In November 2018, the defendant pleaded guilty. He had immigrated from the Dominican Republic approximately three years earlier as a lawful permanent resident. During the plea colloquy, the judge delivered the standard statutory warnings regarding potential immigration consequences and specifically asked plea counsel whether he had discussed any immigration consequences with his client pursuant to Clarke. Counsel responded affirmatively. The defendant received a suspended six-month sentence with probation conditions including maintaining employment and committing no further violations.

Approximately two years and three months later, in February 2021, immigration officials detained the defendant upon his return from the Dominican Republic with his family. According to the defendant, officials informed him for the first time that his conviction subjected him to removal proceedings and deportation. The immigration consequences of his conviction were unambiguous under federal law: 8 U.S.C. § 1227(a)(2)(B)(i) renders deportable any alien convicted of a controlled substance violation other than simple possession of 30 grams or less of marijuana. The Supreme Judicial Court has previously recognized that defendants convicted of possession with intent to distribute have “virtually no avenue for relief from deportation” under this provision. DeJesus.

In April 2022, the defendant moved to withdraw his guilty plea, alleging ineffective assistance of counsel. He submitted two supporting affidavits. In his own affidavit, the defendant averred that while plea counsel advised him a guilty plea would prevent him from obtaining citizenship, counsel never warned him that the plea would terminate his permanent resident status and render him automatically deportable without eligibility for relief. The defendant also averred that had he known the true consequences, he would have rejected the plea and either sought a disposition avoiding immigration consequences or proceeded to trial.

Plea counsel’s affidavit stated that he “would have explained” to the defendant that he would be “subject to deportation but not that he would be automatically deported, mandatorily detained” by federal immigration authorities, “and ineligible for any relief in Immigration Court.” Counsel further averred that he now understood such advice was constitutionally inadequate under Padilla v. Kentucky, 559 U.S. 356 (2010), and DeJesus.

The motion judge, who had also presided over the plea, denied the motion without an evidentiary hearing. He found the defendant’s affidavit not credible because it was submitted four years after the plea and was self-serving, though he acknowledged it was corroborated by plea counsel’s affidavit. As for counsel’s affidavit, the judge discredited it on the basis that it contradicted counsel’s representation during the colloquy that he had advised his client of immigration consequences pursuant to Clarke. The Appeals Court affirmed, and the Supreme Judicial Court granted further appellate review.

Analysis

The Court began by setting forth the applicable standard of review. A motion to withdraw a guilty plea is treated as a motion for a new trial, and appellate courts review the denial of such a motion without an evidentiary hearing for significant legal error or abuse of discretion. Where the motion judge also presided over the plea, substantial deference applies. Nevertheless, the Court stated that judicial discretion is “not boundless and absolute,” quoting Commonwealth v. Kolenovic, 32 N.E.3d 302 (2015). The reviewing court will reverse where the judge’s decision reflects “a clear error of judgment in weighing the factors relevant to the decision … such that the decision falls outside the range of reasonable alternatives.” L.L. v. Commonwealth, 20 N.E.3d 930 (2014).

To obtain an evidentiary hearing, a defendant’s motion and affidavits must present a “substantial issue.” This inquiry requires examining both the seriousness of the issue and the adequacy of the defendant’s showing. The defendant need not prove the claim but must present “sufficient credible information to cast doubt on the issue.” Commonwealth v. Denis, 814 N.E.2d 1080 (2004).

The Court concluded that the defendant’s claim of ineffective assistance raised a serious issue of constitutional magnitude. Under Padilla and its Massachusetts counterpart Commonwealth v. Sylvain, 995 N.E.2d 760 (2013), counsel has a constitutional duty to advise noncitizen clients whether a guilty plea carries a risk of deportation. The Court observed that preserving a client’s ability to remain in the United States “may be more important to the client than any potential jail sentence.”

Turning to the adequacy of the defendant’s showing, the Court examined the judge’s sole stated reason for discrediting plea counsel’s affidavit, i.e., that it contradicted counsel’s colloquy representation of compliance with Clarke. The Court determined this reasoning was flawed because the two statements were not inherently inconsistent.

The Court traced the evolution of the governing legal framework. The Clarke Court held that Padilla applied retroactively and summarized the U.S. Supreme Court’s holding using various formulations, including that counsel must advise a client that a plea “likely would” result in deportation, would cause “virtually automatic deportation,” or “carries a risk of deportation.” Importantly, Clarke also stated that counsel must advise a client that conviction “made him subject to deportation.” Thus, the Court concluded that counsel’s affirmation during the colloquy that he complied with Clarke and his subsequent averment that he only told the defendant he would be “subject to” deportation were not contradictory.

The Court explained that DeJesus later clarified the precise nature of counsel’s obligation where federal law clearly mandates deportation. The DeJesus Court held that counsel must convey “in language that the client could comprehend, the information that presumptively mandatory deportation would have been the legal consequence of pleading guilty.” DeJesus determined the advice that the defendant was “eligible for” or “subject to” deportation insufficient because it failed to communicate the practical inevitability of removal.

Because plea counsel’s colloquy statement and his affidavit could both be truthful – counsel may have believed his advice satisfied Clarke while now recognizing it fell short of DeJesus – the judge’s determination that the affidavit was contradictory and therefore not credible constituted an abuse of discretion, the Court ruled. It acknowledged that counsel may in fact have provided adequate advice contrary to his averments but stated that this possibility highlighted the necessity of an evidentiary hearing rather than resolving the ambiguity on the papers alone.

The Court declined to address alternative grounds the Commonwealth raised, including the conditional phrasing of counsel’s affidavit, noting the judge had not relied on those rationales. The Court likewise declined to reach the prejudice prong of the ineffective assistance analysis, remanding instead for further proceedings.

Conclusion

Accordingly, the Court vacated the order denying the defendant’s motion to withdraw his guilty plea and remanded the case for further proceedings consistent with its opinion. See: Commonwealth v. Santana, 2026 Mass. LEXIS 47 (2026).

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