Democrats hesitant to condemn Sheriff Tompkins, a party fixture, as he faces federal charges

As he rose up through Boston’s Democratic political circles, Suffolk County Sheriff Steven Tompkins built a reputation as a friendly and easy-going team player.

He counts former sheriff and state public safety secretary Andrea Cabral as a “dear friend,” and has described Boston Mayor Michelle Wu as “like family to me.”

That image took a big hit last week when FBI agents arrested him in Florida and federal prosecutors charged him with extorting a local cannabis business. WBUR has reported that company is Ascend Wellness Holdings.

Despite those serious charges, Tompkins’ fellow Democrats have so far proven reluctant to cast judgment or call for his resignation.

“The information that I’ve seen through the initial documents certainly reflects some pretty serious allegations,” Wu told reporters Tuesday. Asked if he should resign, Wu demurred, saying she was “waiting to see what the information will show when more comes out.”

Gov. Maura Healey also has yet to call for Tompkins’ resignation, despite pressure from her rivals in the governor’s race.

“The allegations are certainly serious, and no one in elected positions should ever use or abuse their power,” she said Monday. “I need to get more information.”

Tompkins, 67, has spent years building clout and goodwill within the party. His background is primarily in marketing and communications — he worked for the Dimock Community Health Center and AT&T Cable before joining the Suffolk County Sheriff’s Office in 2002. He’s a Boston College graduate with a master’s degree in public affairs from UMass.

Tompkins was a senior advisor on Elizabeth Warren’s 2012 Senate campaign, where he worked alongside Michelle Wu. The next year he was part of Wu’s successful at-large city council campaign.

When Gov. Deval Patrick named then-Suffolk County Sheriff Cabral as his public safety secretary in 2013, he chose Tompkins, Cabral’s communications chief, to take her place.

“As a dedicated public servant on the frontlines of crime prevention and reentry rehabilitation, Steven brings first-hand knowledge and passion to this critical position," Patrick said at the time.

Suffolk County sheriff is a relatively low-profile job, primarily overseeing two county jails. But it’s a political position with a Boston perch and a broader voice in law enforcement. The sheriff oversees some 1,000 employees and roughly 1,500 prisoners, many awaiting trial and others serving short sentences.

Being sheriff provided Tompkins unique opportunities. As sheriff, prosecutors say Tompkins was an essential part of Ascend's application to open a cannabis business in Massachusetts, promising to work with the company to refer people released from jail for reentry.

And until this week, Tompkins served as chair of the board of Roxbury Community College. He resigned from that position in a letter to Gov. Healey on Tuesday, without specifying why or referring to the charges he’s facing.

Tompkins is an active campaigner and generous with his endorsements. In 2015 the Massachusetts Ethics Commission fined him for asking local store owners to remove his opponent’s campaign signs from their windows.

And he doesn’t shy away from public attention — he’s produced dozens of video podcasts, “Real Talk in the Commonwealth,” to which he’s invited a roster of politicians for wide-ranging conversations.

In one episode, he introduces Wu during the 2021 mayoral campaign. Tompkins describes her as “someone who is near and dear to my heart, someone who is just like family to me.” Wu returned the praise, calling the sheriff “a mentor and a friend.”

Speaking to then-city councilor and mayoral hopeful Andrea Campbell in a podcast during the same campaign season, the sheriff and the future attorney general caught up on friends and family before diving into the interview. “You’re the best,” Campbell said.

So it’s perhaps no surprise that Tompkins’ political allies have been slow to react to the extortion charges against him. Federal prosecutors allege that he pressed an Ascend executive to grant him $50,000 of pre-IPO shares in the company. At first the stock shares jumped, but when they later sank, Tompkins allegedly badgered the executive to return his $50,000.

Yet in other cases where politicians find themselves in the courtroom, local leaders have been quicker to call for their resignations. When prosecutors filed federal corruption charges against Boston City Councilor Tania Fernandes Anderson late last year, Mayor Wu urged the councilor to step down the same day. Wu said the “serious nature of these charges undermine the public trust,” and would prevent the councilor from effectively serving the city.

Gov. Maura Healey, too, has taken swift aim in other cases, like when Cape Cod State Rep. Chris Flanagan was arraigned on federal fraud charges this spring. Healey said he should resign, because the allegations threatened to “undermine” the work of the Legislature.

In a press statement Wednesday, Republican gubernatorial candidate Brian Shortsleeve, a businessman and former MBTA chief administrator, said, “The silence coming from the governor’s office is deafening.” Former housing secretary Mike Kennealy, who’s also running for governor as a Republican, said Healey’s “inaction shows she either lacks the leadership to make the tough calls required of a governor or chose to protect a political ally.”

The power to remove a sheriff lies with the state’s highest court; the governor and attorney general can petition for removal but do not have authority over the sheriffs. Voters could also initiate a recall election.

Campbell, now the state attorney general, hasn't spoken publicly about Tompkins. A spokesperson didn't respond to a request for comment.

Cabral said she took the job after getting a call from “your friend and mine, Frank Perullo”

Andrea Cabral, former Ascend Mass. CEO

It’s unclear if there are more charges to come in this case. The U.S. Attorney has portrayed Ascend as the victim, said attorney George Varghese, a former federal prosecutor. Companies need to be careful in situations like this, he said, because they could potentially be accused of bribery.

" It's a fine line between being a victim and being a knowing conspirator," he said.

Cabral, Tompkins’ old boss, also worked for Ascend. At the time of a 2021 podcast interview with the sheriff, she was the Massachusetts chief executive of the company.

Cabral said she took the job after getting a call from “your friend and mine, Frank Perullo,” a Massachusetts political lobbyist who was seeking to get into the cannabis business by helping launch Ascend.

Cabral reportedly stepped away from the company sometime around 2022. Neither she nor anyone else from Ascend is named in the indictment, and prosecutors have not named the individual at the company whom Tompkins allegedly extorted.

But in financial disclosures in 2020 and 2021, Tompkins reported a stake in a company called Cannanovus LLC. Public records at the Secretary of State's office show Perullo controlled a company called Cananovus (with one n), described as an investment and holding vehicle.

A filing with the state's Cannabis Control Commission from that period lists Perullo as having 100% ownership of Ascend Mass., meaning he would have been a key figure able to agree to give Tompkins the IPO shares.

Tompkins and his representatives have not responded to multiple requests for comment since his arrest. Neither have Perullo, Cabral or Ascend co-founder Abner Kurtin.

As the two signed off from their 2021 podcast conversation, Tompkins wished Cabral well in the cannabis industry: “Enjoy your new position and what you’re doing and make lots and lots and lots and lots of friends and money,” he said.

Ascend has three locations in Massachusetts and 44 nationally, according to its website. In the first six months of this year, the company reported $255.3 million in revenue and a $43.7 million loss, according to a filing with securities regulators.

Meanwhile, its founders took in a big haul in 2024, according to a proxy filing: Nearly $5 million in cash and stock for executive chairman Kurtin and $3.8 million for Perullo.

Tompkins was released from custody in Florida last week on $200,000 bond and ordered to check in with pre-trial services in Massachusetts by Friday.

In an interview with WBUR, Bristol County Sheriff Paul Heroux, a Democrat, stressed that Tompkins is “presumed innocent until proven guilty."

"Politicians are people, and they sometimes make mistakes," Heroux said.

The Massachusetts Sheriffs’ Association declined to comment on the charges against Tompkins, the group’s former president, saying it would “respect the parties in this case, and allow the legal process to play out.”