Commonwealth v. Santana

Massachusetts Supreme Judicial Court·Decided February 4, 2026·No. SJC 13720·Published

Opinion

NOTICE: All slip opinions and orders are subject to formal revision and are superseded by the advance sheets and bound volumes of the Official Reports. If you find a typographical error or other formal error, please notify the Reporter of Decisions, Supreme Judicial Court, John Adams Courthouse, 1 Pemberton Square, Suite 2500, Boston, MA, 02108-1750; (617) 557- 1030; SJCReporter@sjc.state.ma.us

SJC-13720

COMMONWEALTH vs. JORGE L. SANTANA.

Essex. September 8, 2025. - February 4, 2026.

Present: Budd, C.J., Gaziano, Kafker, Wendlandt, Georges, Dewar, & Wolohojian, JJ.

Practice, Criminal, Plea, Assistance of counsel, Affidavit, Findings by judge, Judicial discretion. Constitutional Law, Plea, Assistance of counsel. Alien. Controlled Substances.

Complaint received and sworn to in the Salem Division of the District Court Department on June 6, 2017.

A motion to withdraw a guilty plea, filed on April 21, 2022, was heard by Allen G. Swan, J.

After review by the Appeals Court, 104 Mass. App. Ct. 1117 (2024), the Supreme Judicial Court granted leave to obtain further appellate review.

Casey L. Riley (Danya Fullerton also present) for the defendant. Jennifer D. Cohen, Assistant District Attorney, for the Commonwealth. Jennifer Klein & Caitlin Perry, Committee for Public Counsel Services, Edward Crane, & Maria Durant, for Committee for Public Counsel Services & another, amici curiae, submitted a brief. 2

WENDLANDT, J. In 2018, the defendant, Jorge Santana, a

noncitizen lawfully residing in the United States, pleaded

guilty to possession of a controlled substance with intent to

distribute, subjecting him to automatic deportation from the

United States. This case presents the question whether the

defendant has made an adequate showing to warrant an evidentiary

hearing on his motion to withdraw his plea on the basis that

plea counsel failed to inform him that his plea rendered his

deportation virtually mandatory in violation of his

constitutional right to the effective assistance of counsel.

See Padilla v. Kentucky, 559 U.S. 356, 374 (2010) (Sixth

Amendment to United States Constitution requires counsel to

advise client whether plea carries risk of deportation);

Commonwealth v. Sylvain, 466 Mass. 422, 436 (2013), S.C., 473

Mass. 832 (2016) (same under art. 12 of Massachusetts

Declaration of Rights).

The motion judge, who was also the plea judge, denied the

motion without an evidentiary hearing primarily on the basis

that plea counsel's affidavit averring that he did not tell the

defendant that he would be automatically deported was not

credible because it was inconsistent with counsel's

representation during the plea colloquy that he had discussed

the immigration consequences of the plea with his client. 3

Contrary to the judge's determination, however, counsel's

affidavit was not inherently inconsistent with his

representations during the colloquy and any inconsistency could

not be resolved on the papers alone. Accordingly, we vacate the

denial of the motion to withdraw the defendant's guilty plea and

remand for further proceedings consistent with this opinion.1

1. Background. In June 2017, an officer of the Danvers

police department (first officer) observed the defendant, who

was in a vehicle, exchange items with a known heroin user, who

was in a different vehicle, in a supermarket parking lot.

Suspecting that the exchange involved illegal drugs, the first

officer followed the defendant's vehicle for several minutes and

eventually instructed a second officer, whose cruiser was closer

to the defendant, to initiate a stop. As the first officer

approached the defendant's vehicle, he observed the defendant

"struggling to swallow something." Upon opening the defendant's

mouth, he saw "two plastic baggies containing a light tan

powder" consistent with heroin. A subsequent search yielded

three tightly folded one hundred dollar bills, an additional

$790 in cash, and paraphernalia consistent with the storage and

concealment of illegal drugs. The defendant was arrested and

charged with one count of possession with intent to distribute a

1 We acknowledge the amicus brief submitted by the Committee for Public Counsel Services and Boston Bar Association. 4

class A controlled substance (heroin), in violation of G. L.

c. 94C, § 32 (a).2

a. Plea colloquy. In November 2018, the defendant, who

was born in the Dominican Republic, pleaded guilty to the

charge; he had immigrated to the United States approximately

three years earlier as a legal permanent resident. Relevant to

the issue on appeal, after issuing the standard oral warnings,3

2 Pursuant to G. L. c. 94C, § 32 (a), a person convicted of possession of a class A controlled substance with intent to distribute may be sentenced to imprisonment "for not more than ten years" in State prison or "for not more than two and one- half years" in a house of correction.

3 At the plea colloquy, the judge advised the defendant as required by G. L. c. 278, § 29D, which provides:

"If you are not a citizen of the United States, you are hereby advised that the acceptance by this court of your plea of guilty, plea of nolo contendere, or admission to sufficient facts may have consequences of deportation, exclusion from admission to the United States, or denial of naturalization, pursuant to the laws of the United States" (emphasis added).

He also advised the defendant pursuant to a prior version of Mass. R. Crim. P. 12 (c) (3) (A) (iii), as appearing in 470 Mass. 1501 (2015), then in effect, which provided:

"[I]f the offense to which the defendant is pleading guilty, nolo contendere, or admitting to sufficient facts is under federal law one that presumptively mandates removal from the United States and federal officials decide to seek removal, it is practically inevitable that this conviction would result in deportation, exclusion from admission, or denial of naturalization under the laws of the United States" (emphases added).

"[S]uch warnings are 'not an adequate substitute for defense counsel's professional obligation to advise her client of the 5

the judge specifically asked plea counsel, "[I]f there are any

immigration consequences [of this plea], have you discussed

those pursuant to Commonwealth against Clarke?" See

Commonwealth v. Clarke, 460 Mass. 30 (2011). Counsel replied,

"Yes, I have, Your Honor." After accepting the plea, the judge

sentenced the defendant to six months of incarceration,

suspended for one year with conditions of probation, including,

inter alia, that he maintain employment and commit no further

violations of the law.4

likelihood of specific and dire immigration consequences that might result from such a [guilty] plea.'" Commonwealth v. DeJesus, 468 Mass. 174, 177 n.3 (2014), quoting Commonwealth v. Clarke, 460 Mass. 30, 48 n.20 (2011).

4 The defendant and plea counsel signed the standard tender of plea form, which included an acknowledgement by the defendant that a guilty plea may have immigration consequences and an affirmation by plea counsel that he "explained to the defendant the legal rights and consequences referred to" in the form. The plea judge noted on the defendant's tender of plea form: "Counsel has advised immigration consequences." Specifically, the form restated the warnings that the judge orally delivered pursuant to G.

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