NH man was banished from Boston for a laundry list of thefts. Can a judge do that?

Two days before last Halloween, Timothy Dearborn and an accomplice were caught trying to pry open the valet ticket machine in the Boston Medical Center parking garage. One night a month later, he broke into a Taco Bell on Summer Street and robbed the cash register. As Christmas approached, he stole a package of holiday gifts from an address near the Boston Common.

But Dearborn‘s thievery is over, at least for now. By order of a judge, the 41-year-old New Hampshire man, who moved to Boston last year, will be banished from the city for three years after completing an 18-month prison sentence.

The city-wide ban and jail sentence were part of a plea agreement Dearborn reached with prosecutors last month covering a laundry list of charges for thefts, break-ins and incidents evidently involving substance abuse, Suffolk District Attorney Kevin Hayden’s office said last week.

Dearborn ”epitomizes the type of repeat offender who makes life harder for merchants, consumers and residents,” Hayden said.

“He also represents the type of offender who has moved beyond any hopes of alternative sanctions and must be dealt with at another level,” the district attorney added. “His incarceration, followed by his expulsion from Boston for three years, is a win for merchant safety and neighborhood quality of life.”

Stay-away orders, like the one intended to keep Dearborn out of Boston, are regularly issued by judges as conditions for bail or as part of sentences, Tina Nguyen, a spokesperson for the district attorney, said.

“Some are from particular stores, in the case of shoplifting, or particular neighborhoods, or MBTA stations, or, in this case, the entire city,” she continued.

Jack Lu, a retired Superior Court judge, told MassLive that a city-wide banishment is rare, compared to more common cases of a judge banning a person from entering a specific business district or the neighborhood of a crime victim.

Interestingly, he noted, while Hayden’s press release described the ban as being citywide, the court docket for Dearborn’s case listed a ban from “Downtown Crossing/Boston.”

“I’m not sure exactly what that means, but ambiguous probation terms are construed in favor of the defendant,” Lu wrote in an email. “That probably does not mean all of Boston and probably means just Downtown Crossing, a fairly small area.”

The Supreme Judicial Court has signaled some uneasiness with “stay out-of-town” orders, considering citywide bans as overly restrictive on defendants’ liberty, Lu said.

In one prior case he pointed to, Commonwealth v. Rodriguez, the state’s high court “basically indicated its general skepticism of this kind of broad order and vacated the ‘stay out of town’ provision,” Lu said. However, he added, the court’s decision in that case was ultimately based on procedural issues, not the severity of the sentence.

And in Dearborn’s case, Lu said, the defendant apparently reached the agreement with prosecutors voluntarily, and thus wouldn’t have the ability to appeal his conviction.

From October 2024 through May 2025, Dearborn repeatedly earned the attention of Boston Police for thefts, break-ins and trespassing incidents in the Downtown Crossing area.

He was charged with larceny from a building for one late-night foray into a High Street office tower last December, where he was caught on camera rummaging through desk cabinets and the pockets of a jacket at the concierge desk before leaving with a label maker and another unknown object, prosecutors said.

That same month, Dearborn broke into a Planet Fitness on Christmas Day and stole a safe, broke into a Winter Street building and left with a pregnancy pillow and Amazon packages, and broke into a Dunkin’ on Kneeland Street and took about $150 from a cash register, according to prosecutors.

In January, Dearborn entered a Citizens Bank on High Street through an unlocked side door and dug through multiple bank offices. He departed with a cardboard box containing a Bose speaker, a digital projector and other items. Late that night, he hopped the counter at Faneuil Hall’s Boston Chowda Co. and stole more than $1,100 from a closed but unlocked safe, prosecutors said.

Many of the break-ins were captured on video, they said.

Stay-away orders may be enforced by GPS monitoring, but can also be enforced by the threat of reincarceration for violations, Nguyen said.

After completing his jail term at the Suffolk County House of Correction, Dearborn risks spending up to another year behind bars for reentering Boston. Judge Paul Treseler also ordered him to undergo treatment for mental health.