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Appeals Court of Massachusetts.



Decided: November 17, 2022

By the Court (Desmond, Sacks & D'Angelo, JJ.1)


In January 2020, the defendant, Escobar Gonzalez, pleaded guilty to one count of possession of a class B substance with intent to distribute under G. L. c. 94C, § 32A. He now appeals from the denial of his subsequent motion to withdraw his guilty plea, arguing, inter alia, that he received ineffective assistance of counsel because trial counsel failed to warn him about the specific immigration consequences of his plea. We reverse.

Background. The defendant was born in Guatemala in 1998. He had a difficult childhood and adolescence that involved both neglect and abandonment. His parents left him behind when he was three years old as they immigrated to the United States. He initially lived with his paternal grandmother; although she provided for him, she often beat him with a hose. When he moved to live with his maternal grandmother, also in Guatemala, his father stopped providing financial support. Gang activity was common in his community, and he stopped attending school at the age of fifteen because he was unsupported.

The defendant immigrated to the United States when he was sixteen years old. He had a strained relationship with his parents given their limited role in his life and experienced homelessness during this time. During a period of homelessness, he broke into a home and was committed to the custody of the Department of Youth Services (DYS). He was able to learn English and obtain his high school diploma while in DYS custody, in addition to receiving other support.

A Juvenile Court judge entered an order in March 2019 finding that the defendant was dependent on the Juvenile Court and unable to reunite with his parents due to abuse and neglect. The judge further held that returning to Guatemala was not in the defendant's best interest. Shortly thereafter, in April 2019, the defendant's application for immigration relief under Special Immigration Juvenile (SIJ) status was received by the United States Citizenship and Immigration Services. That application remains pending.

The offense at issue here occurred on October 13, 2019, at approximately 4 p.m., when Chelsea police responded to a report of a large group fighting with knives on Shawmut Street. Upon arrival, two males fitting the description provided by the caller were observed and fled once they saw the officers. The officers gave chase, but to no avail. Shortly thereafter, two men also fitting the description of “young Hispanic males” were observed by the officers. As the officers approached the men, they avoided eye contact and attempted to walk by the officers when the officers asked to speak with them. The defendant was one of these men. Police detained them both and, just prior to conducting a patfrisk, observed the defendant toss a plastic bag on the ground. The bag contained thirteen smaller bags, each one holding a white, rock-like substance, which the police believed to be “crack” cocaine.2

The defendant was charged with one count of possession of a class B substance with intent to distribute under G. L. c. 94C, § 32A, and was subsequently appointed an attorney (plea counsel) by the Committee for Public Counsel Services. As part of his pretrial advice, plea counsel recalled providing immigration advice to the defendant but did not recall the specific content of that advice. His practice at the time was to tell all his clients that “convictions can have consequences for immigration purposes.”

Relying on plea counsel's advice, the defendant pleaded guilty to the charged offense in January 2020 and was sentenced to serve one year in the house of correction, concurrent with a prior sentence he was already serving.3 During the plea colloquy, the judge advised the defendant that “if the offense to which [he was] pleading guilty [was] ․ one that presumptively mandate[d] removal from the United States and Federal officials decide[d] to seek that removal it [was] practically inevitable that this disposition would result in deportation.” The defendant stated that he understood this warning.

As a result of his guilty plea, the defendant became ineligible to obtain SIJ status and was transferred to an Immigration and Customs Enforcement facility in Pennsylvania to await deportation. Represented by new counsel, he moved to withdraw his guilty plea on April 23, 2021. The motion to withdraw the plea, to which the Commonwealth assented, was heard on April 28, 2021.4 In a thoughtful written decision the judge denied the motion on May 11, 2021.

Discussion. 1. Ineffective assistance of counsel. “A motion to withdraw a guilty plea is treated as a motion for a new trial pursuant to Mass. R. Crim. P. 30 (b).” Commonwealth v. Sylvain, 473 Mass. 832, 835 (2016), quoting Commonwealth v. DeJesus, 468 Mass. 174, 178 (2014). See Mass. R. Crim. P. 30 (b), as appearing in 435 Mass. 1501 (2001). We review the denial of such a motion “for a significant error of law or other abuse of discretion.” Sylvain, supra at 835, quoting Commonwealth v. Lavrinenko, 473 Mass. 42, 47 (2015). See Commonwealth v. Gordon, 82 Mass. App. Ct. 389, 393-394 (2012). To establish that he is entitled to a new trial, the defendant is required to show that, by not advising him of the immigration consequences he would face if convicted of possession with the intent to distribute a class B substance, (1) his plea counsel's conduct fell below the standard of an ordinary, fallible lawyer, and (2) that shortcoming prejudiced him in some way. See Commonwealth v. Saferian, 366 Mass. 89, 96 (1974). See also Lavrinenko, supra at 51-52 (ineffective assistance of counsel on immigration consequences of plea).

a. Performance. “In determining whether the defendant met his burden under the performance prong of the Saferian standard, we must first address what level of advice plea counsel w[as] constitutionally required to provide the defendant given the charges against him.” Commonwealth v. Henry, 88 Mass. App. Ct. 446, 452 (2015). When the immigration consequences of a plea are “truly clear,” then “the duty to give correct advice is equally clear.” Commonwealth v. Chleikh, 82 Mass. App. Ct. 718, 723 (2012), quoting Padilla v. Kentucky, 559 U.S. 356, 369 (2010). See Sylvain, 466 Mass. at 436 (“defense counsel [has] a duty to inform a noncitizen client that conviction, whether by plea or by trial, may carry adverse immigration consequences” [citation omitted]). This means that, when deportation is virtually certain to result from a guilty plea, the defendant must be informed of that consequence explicitly. See Chleikh, supra.

We conclude that plea counsel's advice to the defendant fell below that of an ordinary, fallible lawyer. As discussed supra, plea counsel provided an affidavit averring that it was his practice at the time to tell his clients that “convictions can have consequences for immigration purposes.” This advice was insufficient and failed to satisfy the Saferian standard because the charge to which the defendant pleaded guilty was almost certain to result in his deportation under 8 U.S.C. § 1182(a)(2)(A)(i)(II), (C). See DeJesus, 468 Mass. at 181 (warning of mandatory deportation must be given when such outcome is clear). Because deportation was virtually certain to result as the result of his guilty plea, plea counsel was required to explicitly inform the defendant of that certainty. See Padilla, 559 U.S. at 369. See also DeJesus, supra. It is undisputed that plea counsel failed to do that in this case.

b. Prejudice. “In the context of a guilty plea, in order to satisfy the ‘prejudice requirement,’ the defendant has the burden of establishing that ‘there is a reasonable probability that, but for counsel's errors, he would not have pleaded guilty and would have insisted on going to trial.’ ” Lavrinenko, 473 Mass. at 55, quoting Commonwealth v. Clarke, 460 Mass. 30, 47 (2011). To establish that reasonable probability, “[a]t a minimum, ․ the defendant must aver that to be the case.” Lavrinenko, supra, quoting Clarke, supra. Having made such an assertion, “[the defendant] must [then] convince the court that a decision to reject the plea bargain would have been rational under the circumstances” (quotations omitted). DeJesus, 468 Mass. at 183, quoting Clarke, supra. “To prove that rejecting the plea would have been rational under the circumstances, ‘the defendant bears the substantial burden of showing that (1) he [or she] had an “available, substantial ground of defence,” ․ that would have been pursued if he [or she] had been correctly advised of the dire immigration consequences attendant to accepting the plea bargain; (2) there is a reasonable probability that a different plea bargain (absent such consequences) could have been negotiated at the time; or (3) the presence of “special circumstances” that support the conclusion that he placed, or would have placed, particular emphasis on immigration consequences in deciding whether to plead guilty’ ” (footnote omitted). Lavrinenko, supra at 55-56, quoting Clarke, supra at 47-48.

With the foregoing principles in mind, we conclude that the defendant was prejudiced by his plea counsel's errors. The defendant stated in his affidavit that he would not have pleaded guilty but for his plea counsel's poor advice. Having done so, he has satisfied the threshold requirement necessary to show a reasonable probability that he would not have pleaded guilty. See Lavrinenko, 473 Mass. at 55.

Furthermore, the decision to reject the plea bargain would have been rational under the circumstances for two reasons. First, the defendant had an “available, substantial ground of defence.” Clarke, 460 Mass. at 47, quoting Saferian, 366 Mass. at 96. Although the defendant was found with thirteen individually wrapped packages of a substance that was suspected to be crack cocaine, mere possession of individually wrapped packages alone does not establish probable cause of an intent to distribute the narcotics. See Ilya I., 470 Mass. at 629 (individual packaging of narcotics does not establish probable cause for intent to distribute where total quantity of narcotics is small). See also Commonwealth v. Sepheus, 468 Mass. 160, 165-166 (2014) (individual packages do not support inference of intent to distribute in absence of other evidence).5 Without more, the Commonwealth's chance of obtaining a conviction was not as certain as plea counsel mistakenly believed.6

Second, the defendant had been working with an immigration attorney to obtain SIJ status and remain lawfully in the United States. In his affidavit in support of his motion, he has stated that he has fewer job prospects in Guatemala and fears for his life if he is forced to return there, due to gang violence. Those representations “support the conclusion that he placed, or would have placed, particular emphasis on immigration consequences in deciding whether to plead guilty.” Lavrinenko, 473 Mass. at 56, quoting Clarke, 460 Mass. at 47-48. Taken together, these assertions are sufficient to support a reasonable probability that a reasonable person in the defendant's position would not have pleaded guilty but for plea counsel's errors.7 See Commonwealth v. Lys, 481 Mass. 1, 7-8 (2018); Lavrinenko, supra at 55, 58-59 (special circumstances, such as noncitizen's desire to remain United States, must be given substantial weight in determining prejudice).

Order denying motion to withdraw guilty plea reversed.


2.   Crack cocaine is a class B substance. See G. L. c. 94C, § 31.

3.   The defendant had already been sentenced to one year in the house of correction for a probation violation leveled as a result of the current charge.

4.   During the motion hearing, the Commonwealth asserted that (1) the defendant received insufficient immigration warnings from plea counsel, (2) the evidence supporting conviction was not strong, and (3) the defendant could have made a viable motion to suppress the narcotics evidence due to insufficient articulable facts to support the initial stop. See Commonwealth v. Lavrinenko, 473 Mass. 42, 51-52 (2015); Commonwealth v. Ilya I., 470 Mass. 625, 629 (2015).

5.   Although the question of what quantity is needed to establish possession with intent to distribute is disputable, the Commonwealth agrees that the charge here was not supported with overwhelming evidence.

6.   The Commonwealth also acknowledged, during the hearing on the motion to withdraw the plea, that “there was a viable motion to suppress.” Additionally, the Commonwealth conceded that the description of “young Hispanic males” was not sufficiently detailed to permit a stop and frisk in this instance. See Commonwealth v. Narcisse, 457 Mass. 1, 6-7 (2010) (to conduct stop, officers must “reasonably suspect[ ] that the person apprehended is committing or has committed a criminal offense”).

7.   Having concluded that the defendant did not receive effective assistance of counsel for the aforementioned reasons, we need not reach the merits of his other arguments.

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Docket No: 21-P-992

Decided: November 17, 2022

Court: Appeals Court of Massachusetts.

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