Suffolk County Sheriff Steven Tompkins pleaded not guilty to two federal felony charges of extortion at a federal court hearing in Boston Thursday.
“The facts will demonstrate that he was charged with a crime he did not commit,” Martin Weinberg, Tompkins’ attorney, said in brief remarks to the media afterward.
Neither Weinberg nor Tompkins, who wore a blue suit, white shirt and no tie for the hearing, took questions afterward. Tompkins ignored multiple shouted queries about whether he plans to stay in his job as the trial proceeds. But Weinberg may have offered a clue to the answer when he predicted that, in approximately one year, the media gathered for Tompkins’ trial would watch him being found not guilty.
Tompkins was indicted earlier this month and initially arrested in Florida, where he posted $200,000 bail before returning to Massachusetts.
He is accused of pressuring an official with a cannabis company doing business in Massachusetts, which has not been described in court filings but has been widely identified as Ascend Wellness, to allow him to purchase $50,000 in stock prior to an initial public offering, and subsequently demanding the return of his full $50,000 when the value of his shares dropped after the IPO.
The leverage Tompkins had in his alleged scheme, prosecutors contend, was that a requirement that cannabis companies operating in parts of Massachusetts negatively impacted by cannabis prohibition and the War on Drugs demonstrate that they were making a positive social impact.
Under Tompkins, the Suffolk Country Sheriff’s Department has worked with Ascend to connect formerly incarcerated individuals with jobs as they reentered the community. At the time the alleged extortion took place, according to the indictment, an unnamed Ascend Wellness executive feared Tompkins would terminate that partnership, jeopardizing both the license Ascend already had to operate a dispensary in Boston and the company’s upcoming IPO.
Tompkins allegedly made his intentions known by telling an Ascend executive he “wanted to get in on the stock so [he] could make some cannabis money,” and by reminding the executive that the his department had played a crucial role in the licensure of a Boston dispensary.
Massachusetts law prohibits state employees from soliciting or obtaining something of value through their official position. Prosecutors say Tompkins was aware of this prohibition because he was previously sanctioned for using his position as sheriff to get local businesses to remove his opponent’s signs while running for election in 2013, and investigated by the State Ethics Commission for allegedly creating a paid position for his niece around 2017, in which she performed childcare for him while on the job.

Tompkins is a fixture on the Massachusetts political scene who has both endorsed and been endorsed by a wide range of progressive and conservative Democrats over the years. For example, he backed Michelle Wu in Boston’s 2021 mayoral race, and served as an advisor to Elizabeth Warren when she defeated Scott Brown for U.S. Senate in 2012.
Since Tompkins’ indictment became public, few if any of his political allies have called on him to step down or temporarily leave his post, opting instead to express concern about the allegations against him and to say they need more information on the case.
Tompkins recently resigned as board chair of Roxbury Community College, but has given no indication that he plans to step aside as sheriff, either temporarily or permanently.