His plight had caught the attention of Rollins’s office, which has made it a priority to help defendants get convictions dismissed when it appeared that they unjustly faced “harsh collateral consequences” under federal immigration law, according to prosecutors.

Osman Bilal was 19 when he pleaded guilty to stealing jewelry from a Boston street vendor in 2011. It was a misdemeanor conviction, but it put him at risk of deportation to a country his family had fled when he was just two days old.

On a morning in November, a top aide to Suffolk District Attorney Rachael Rollins and a defense lawyer appeared in Boston Municipal Court, seeking a new trial for a Somali immigrant.


But in Bilal’s case, the effort to remove the stigma of his criminal past has sparked a swirling courthouse drama — from accusations of prosecutorial deception and judge-shopping to a hushed sidebar and an abrupt departure from the bench — that has risen to the state’s highest court, which scheduled a hearing for Tuesday.

On Nov. 15, Bilal’s case wasn’t listed on the court schedule when his newly appointed attorney, Kelly Cusack, and Donna Jalbert Patalano, general counsel for Rollins, showed up in Judge Michael Coyne’s courtroom to make a joint request for a new trial.

They asked to speak to the judge at sidebar. During a whispered conversation that lasted several minutes, Coyne granted the motion, then chatted amiably with the lawyers as he showed them a photograph of his new grandson, according to a transcript.

Patalano immediately filed a motion known as a nolle prosequi, dismissing the case. “Justice would be served,” she wrote, because Bilal had rehabilitated himself and had a steady job.

As Bilal left the courtroom, the case appeared to be over. The larceny conviction that had made him ineligible to renew his green card would be wiped from his record.


But five days later, an irate Coyne ordered Patalano and Cusack back to court. He accused them of misconduct for failing to tell him that the judge who had accepted Bilal’s guilty plea in 2011 had since denied four motions for a new trial, most recently in July.

“This court finds that the lack of candor and the lack of specific information in the filed affidavit intentionally misled this court in a joint effort by both counsel to circumvent the usual appellate practice and attempt to terminate any subsequent prosecution of this defendant,” Coyne said, according to a transcript of the hearing.

Coyne vacated his order granting Bilal a new trial and reinstated his conviction. He refused to hear objections and abruptly left the bench, prompting a clerk to shut off a recording of the proceedings while Bilal’s lawyer was in mid-sentence.

Coyne returned the case to Judge Sally Kelly, who had sentenced Bilal to probation in 2011. Kelly promptly denied his latest bid, writing that it was “rooted in deception.” She accused the lawyers of trying to sidestep her jurisdiction over the case by presenting it to Coyne on the only day that month she wasn’t in court.

Suffolk prosecutors were undeterred. In a sharp rebuke to the district court, they filed an emergency petition with a single justice of the Supreme Judicial Court, accusing Coyne of overstepping his authority by striking the dismissal of Bilal’s case.

“I committed no misconduct, nor did I fail to be clear with the court of my intention to act in the interests of justice by moving to vacate a misdemeanor conviction that would help Mr. Bilal avoid extreme and unjust collateral consequences from cruel federal immigration laws,” Patalano wrote.


SJC Justice David Lowy has scheduled Tuesday’s hearing on the case, which underscores Rollins’s determination to protect immigrants who face deportation for nonviolent crimes, even if it means taking on the judiciary.

“Mr. Bilal’s case exposes one of the biggest problems with our criminal justice system: It chooses finality over justice,” Rollins said in a statement Sunday. “I ran for office and was elected to change that. And I have. Since taking the oath as District Attorney, I have required that my staff investigate, review, and resolve each case with justice in mind. I also asked that they remedy outcomes that are inconsistent with this mission, that they take positions that are not those of ‘least resistance’ and do so with equity as their guidepost.”

She added, “If someone has truly paid their debt to society, how can we keep requiring them to eternally suffer all of the debilitating collateral consequences that come from a conviction?”

Attorney John Swomley, who represents Cusack in the matter, said there was “no wool being pulled over Judge Coyne’s eyes” and he had Bilal’s full record before him when he granted the new trial.

“I think that what is happening is that Rachael Rollins is ruffling some judicial feathers and, frankly, I think that is a wonderful thing,” Swomley said.


In March, two months after she was sworn in as district attorney, Rollins issued a memo advising prosecutors to alert Patalano if they received motions by defendants “asserting unjust immigration consequences” after their convictions.

In an affidavit filed earlier this month in Bilal’s case, Patalano wrote that she has reviewed more than two dozen cases to determine whether prosecutors should assent to defense requests to vacate convictions and dismiss the cases. The review includes consideration of the defendant’s criminal conduct, criminal history, success at rehabilitation, and “the nature of the defendant’s relationship with family in this country and relatives in his home country,” she wrote.

Patalano wrote that she and Cusack chose Nov. 15 to file their motion for the new trial because it was a date that worked for all the parties. A court clerk sent them to Coyne’s courtroom because Kelly was not sitting that day.

Bilal, now 28, wrote in a court affidavit that he lived in a refugee camp in Saudi Arabia with his parents and seven brothers and sisters for 10 years after fleeing Somalia. They then moved to Syria.

In 2007, several years after his parents divorced, Bilal, his mother, and younger siblings were granted permission to come to the Boston area as refugees.

“I had no father for guidance,” Bilal wrote. “I got caught up with the wrong crowd, and dropped out of school.”

In February 2011, Bilal was on probation for stealing a cellphone at a Tufts University dormitory when he was arrested at the Downtown Crossing MBTA Station for stealing two necklace chains from a man selling jewelry there, court records show. As he was led away in handcuffs, he shouted at the vendor, “I’m gonna come back with my boys . . . bang, bang bang you [expletive],” according to a police report.


Bilal was charged with unarmed robbery and intimidating a witness, a felony. A few months later, the case was resolved with a plea bargain. Bilal pleaded guilty to a reduced charge of larceny under $250 and was placed on probation for a year.

His legal problems did not end there. Six months later, he was arrested in Chelsea and charged with carrying a knife after police confronted him and five other men who appeared to be involved in an argument, according to court records. One of the men had been stabbed but refused to cooperate with police. The charge was dismissed after Bilal completed a term of probation.

In 2016, Bilal filed a motion to withdraw his guilty plea in the larceny case, arguing that his attorney was unaware his immigration status had been changed from that of a refugee to a legal permanent resident. That meant Bilal could not renew his green card because the misdemeanor larceny charge is considered a crime of “moral turpitude,” according to court filings.

“Had I known about the impact that my plea would have on becoming a citizen or even staying in this country, I would have taken my chances at going to trial,” Bilal wrote in an affidavit.

Rollins’s predecessor, Daniel Conley, opposed Bilal’s motion for a new trial and Judge Kelly denied the request, as well as subsequent requests. The appeals court overturned the ruling and ordered Kelly to hold a hearing. In July, after hearing testimony from several witnesses, Kelly rejected Bilal’s bid for a new trial.

In her ruling, Kelly said it was likely that Bilal knew he would face immigration consequences by pleading guilty, but did so because it allowed him to avoid jail and a felony conviction.

Patalano said she became aware of Bilal’s case in September from the staff at More Than Words, a nonprofit organization that works with youths and began mentoring Bilal in 2012.

In a letter filed in court, a director at the organization described Bilal as “a true success story of someone who has overcome significant barriers and moved his life forward as a valued member of the community.”

In another letter, the owner of a North End restaurant said Bilal works 55 to 60 hours a week as a sous chef and “has grown immensely as an employee and as a human being” in his two years there.

In his request for a new trial, Bilal wrote that he has learned how to make better choices. He said he has no family in Somalia and fears for his safety should he be deported.

In her statement, Rollins said she stands firmly behind her decision to support Bilal “in the interest of justice.” She said if his larceny conviction stands, he’ll be deported to a country he only spent two days in decades ago.

“This is the unfortunate state of our federal immigration law,” Rollins said. “Mr. Bilal’s current situation is the very definition of extreme and unjust collateral consequences. We are better than this. I know it.”

Globe correspondent Caroline Enos contributed to this report. Shelley Murphy can be reached at shelley.murphy@globe.com.