Suffolk County Sheriff Steven W. Tompkins was arrested in Florida on Friday, August 8, in connection with a federal investigation into an alleged extortion scheme involving a Boston-based cannabis company. The 67-year-old sheriff is accused of using his official position to unlawfully obtain financial benefits.
Tompkins was taken into custody by federal agents and faces two counts of Extortion Under Color of Official Right. The indictment, unsealed in the District of Massachusetts, alleges that Tompkins pressured an executive of a cannabis company to sell him stock at a pre-initial public offering (IPO) price.
The scheme allegedly began in 2019 when the cannabis company was seeking to open a dispensary in Boston.
The company had entered into a partnership with the Suffolk County Sheriff’s Department as part of its “Positive Impact Plan,” a requirement for licensing in Massachusetts. This partnership involved the sheriff’s office referring graduates of its re-entry program for employment at the cannabis company.
Sheriff conducted extortion scheme when stock value declined
The indictment alleges that Tompkins leveraged this relationship to pressure an executive, identified as “Individual A,” to allow him to purchase $50,000 worth of company stock before it went public.
Fearing that the sheriff could jeopardize their licensing and the partnership, the executive complied. After the company’s IPO, the value of Tompkins’ shares reportedly surged to over $138,000.
However, when the stock’s value later declined, Tompkins allegedly demanded a full refund of his initial $50,000 investment. Despite the shares diminished value, the executive is said to have returned the full amount in five separate payments.

While the cannabis company is not officially named in the indictment, investigative reports have strongly suggested it is Ascend Wellness Holdings, a multi-state operator with a dispensary in Boston.
Sheriff has a history of ethical violations
This is not the first time Sheriff Tompkins has faced scrutiny for his conduct. In 2023, he paid a $12,300 fine for ethics violations, which included creating a position for his niece within the department and having subordinates run personal errands for him.
Furthermore, U.S. Attorney for the District of Massachusetts, Rachael S. Rollins, stated, “The public’s trust in our elected officials is paramount. The allegations against Sheriff Tompkins represent a serious breach of that trust and a betrayal of the office he holds.”
Moreover, Sheriff Tompkins, who has served as the Suffolk County Sheriff since 2013, now faces a legal battle that could result in significant prison time if convicted.
If found guilty, Tompkins could face up to 20 years in prison. He could also serve three years of supervised release, and a $250,000 fine, according to the U.S. attorney’s office.
The case has sent shockwaves through the Massachusetts policing and legal communities. It’s raised serious questions about ethics and oversight in public office.
An attorney for Sheriff Tompkins has not yet issued a public statement on the charges.
