Residents, advocates and business leaders shared mixed views on the federal charges against Suffolk County Sheriff Steve Tompkins, ranging from bewilderment at the alleged corruption to doubts on the severity of the charges. Plus, just days after the indictment, many local leaders —including top politicians — have reserved judgment while the legal process plays out.
Tompkins, who has held the sheriff’s seat for more than a decade, was arrested in Florida last week with federal prosecutors alleging he extorted a cannabis company with operations in Massachusetts.
He resigned from Roxbury Community College’s board of trustees on Tuesday, according to a letter of resignation obtained by GBH News. He has not publicly commented on the charges against him.
Local lawyer and criminal justice reform advocate Carl Williams said Tompkins’ indictment raises concerns about abuse of power.
“It is when we give people enormous amounts of power and it is, a lot of times, unchecked, that has a tendency to lead to corruption,” said Williams.
“There comes a point where people think they can — if the allegations are true — can just get away with things because they have power, because they’re important,” Williams said. “This, if the allegations are true, smacks of that.”
According to the 11-page indictment unsealed last week, Tompkins pressured an official with an unnamed cannabis company to let him buy $50,000 in pre-IPO stock. Identifying details within the indictment point to a company called Ascend Wellness. Later, after the company went public and its stock decreased in price, Tompkins demanded his initial investment back, prosecutors allege.
A press release from the office of the U.S. Attorney for the District of Massachusetts included photos of five checks made out to Tompkins — one with a memo “loan repayment” — to complete the alleged refund.

Williams, who described Tompkins as someone he knows personally, though not well, also expressed surprise at the figure involved in the alleged extortion scheme. State records show Tompkins annual pay rate for the year as $191,000, nearly quadruple the figure at the heart of the extortion charges.
“Fifty thousand dollars?” Williams said incredulously. “That someone could just go off the rails for $50,000 seems bizarre to me.”
Some were immediately skeptical of the validity of the charges against Tompkins.
Kobie Evans, co-owner of Pure Oasis dispensary, admitted he had not read the full indictment, but pointed to the early days of the state’s cannabis industry and said attempts to extract benefits from would-be dispensaries was common.
“If you told me that this happened this week? Yeah, that would be surprising,” said Evans, noting that the state has established clearer rules and guidelines surrounding what demands municipalities can make from prospective dispensaries. “If this happened back in 2020, 2021, then there were a lot of predatory engagements that were happening then,” he said.
“I wouldn’t be surprised if there’s actually no crime here,” Evans told GBH News, noting that the initial news of the allegations against Tompkins did not seem to contain evidence of explicit threats against the individual or the company in question. “It sounded like he was just cheap and he wanted his money back,” he said, adding that: “I don’t know if [Tompkins] had the power to affect the outcome of [the cannabis company’s] trajectory.”
But, prosecutors claim that the individual Tompkins allegedly pressured believed that the sheriff had the power and willingness to jeopardize the company’s licensure. Tompkins had entered into a 2019 agreement whereby the Suffolk County Sheriff’s Department would screen and refer graduates of its re-entry program to the company for hire. That agreement helped the company satisfy a crucial aspect of its license to operate a dispensary.
Tompkins, according to the indictment, told the individual ”on several occasions“ that he wanted to ”take part in the IPO“ and “wanted to get in on the stock so [he] could make some cannabis money.” Later, the indictment said, Tompkins ”increased his pressure“ on the individual by reminding them that he should get stock since he helped the company in its Boston licensing efforts and the company “would continue to need Tompkins’ help for license renewals.”
For attorney Adrienne D. Dean, partner in cannabis law at Cogent Law Group, that part of the indictment shows an implied threat connected to his official capacity as a sheriff that could invoke fear of economic loss.
”On the face, I think it does fit the definition of extortion,“ she said in an interview with GBH News. Dean also noted that a trial may yield further details not required to bring an indictment.
Dean, who has experience helping cannabis companies launch and operate since 2018, acknowledged that there was ”rampant corruption“ as the cannabis industry began blooming, however, she said ”you didn’t necessarily hear about it being a member of law enforcement.“
”The fact that was the sheriff is the standout fact here,“ said Dean, noting the office’s power and importance. ”It’s super shocking if the mayor is like ‘Yes, you need to give me money in order to operate here,’ but for the police? That’s frightening.“
Tompkins, who enjoys wide political support among conservative and liberal Democrats across Suffolk County, has won re-election twice, beating out other Democrats in primaries and facing no opponents in a general since his first election in 2014.
He has become recently increasingly critical of the Trump administration through both a regular column in the Bay State Banner and a vidcast that features Tompkins sharing political opinions in a newsy-styled direct-to-camera format. A second vidcast features Tompkins interviewing both public officials and community leaders.
The indictment also mentions that Tompkins has also had at least two prior run-ins with the law in the past. Both incidents resulted in fines for violating state conflict of interest law in 2023 and 2015.
Still, others pointed to their positive working relationships with Tompkins over the years.
Dwight Robson, executive vice president of operations at the Chelsea-based youth crime prevention organization Roca, said the company’s work needs strong partnerships with police and law enforcement.
“Roca has maintained an excellent working relationship with Sheriff Tompkins and his team, and we look forward to continued collaboration with the Suffolk County Sheriff’s Office in pursuit of our shared goals of saving lives, reducing recidivism and enhancing public safety,” Robson said in a statement to GBH News.
The Suffolk County Sheriff’s Department serves Boston, Chelsea, Revere and Winthrop.
Andrea James, founder and executive director of The National Council For Incarcerated and Formerly Incarcerated Women and Girls, said Tompkins is owed procedural fairness.
“We believe due process must be upheld in all circumstances, and no comments should jeopardize that right,” James said in a statement to GBH News. “Our focus has always been on women and girls, and Sheriff Tompkins has consistently been willing to hear our issues and advocacy, whether he agreed or not. That’s more than most in power in the criminal justice reform space have afforded us.”
Court documents do not yet list an attorney representing Tompkins. He was released on bond last Friday and was unavailable for comment on this story.
A date for his Boston court appearance has not yet been scheduled, according to the federal court docket of his case.