A Boston-area sheriff with a history of dubious behavior and run-ins with Trump administration immigration officials is under arrest on charges of extorting a national cannabis retailer that was doing business in the New England city. 

In a statement, the special agent in charge of the FBI’s Boston division, Ted Docks, said, “From his very first day as Suffolk County Sheriff, Steven Tompkins sought to portray himself as a man of the people – a principled public servant and reformer, devoted to the cause of justice.”

“That’s why it’s beyond disappointing that he’s now accused of gaming a system instituted in the interests of public safety and fair play,” Mr. Docks said. “We believe what the sheriff saw as an easy way to make a quick buck on the sly is clear cut corruption under federal law.”

The United States attorney for Massachusetts, Leah Foley, said in a statement that Mr. Tompkins “is alleged to have extorted an executive from a cannabis company, using his official position as Sheriff to benefit himself.”

“Elected officials, particularly those in law enforcement, are expected to be ethical, honest, and law-abiding – not self-serving,” Ms. Foley said.

She called Mr. Tompkins’s alleged behavior an “affront to the voters and taxpayers who elected him.”

Ms. Foley’s office said that Mr. Tompkins was scheduled to appear in court in Florida on Friday and will appear in federal court at Boston at a later date. 

Boston, where officials have feuded with the Trump administration over its deportation operations, is in Suffolk County. In 2019, Mr. Tompkins ended the sheriff department’s contract with Immigration and Customs Enforcement to provide housing for migrant detainees. 

Immigration officials have frequently expressed frustration with Boston officials for not honoring detainer requests to hold illegal migrants in custody.

Mr. Tompkins was arrested in Florida after a grand jury indicted him on charges of extorting $50,000 from a cannabis business, which is not named in the indictment.

The indictment accuses the sheriff of trying to pressure the company to give him stock so he “could make some cannabis money” in exchange for helping it during its licensing process. The filing says Mr. Tompkins wired $50,000 to buy more than 28,000 shares of the company in 2020.

The filing alleges that in the midst of his 2022 re-election bid, Mr. Tompkins demanded that the company refund him his $50,000 investment, despite the lack of any provision providing for a refund, and the business fretted that he would use his position to block it from renewing its dispensary license. 

The indictment includes images of five checks paid by the company to Mr. Tompkins that were allegedly used to refund his $50,000.

It is not the first time the sheriff has been accused of impropriety. GBH at Boston reports that in 2023, Mr. Tompkins was found to have violated the state’s conflict of interest law when he created a staff position for his niece, and he paid a $12,300 fine. In 2015, he paid a $2,500 fine for flashing his sheriff’s identification when he asked stores to take down campaign signs for his opponent. 

The Suffolk County sheriff’s office did not respond to the Sun’s request for comment by the time of publication.