A Massachusetts Sheriff picked the perfect moment to pressure a Florida cannabis executive and it backfired spectacularly

Massachusetts Sheriff Steven Tompkins thought he found an easy way to line his pockets.

He was dead wrong about that calculation.

And a Massachusetts Sheriff picked the perfect moment to pressure a Florida cannabis executive and it backfired spectacularly.

Sheriff’s get-rich-quick scheme exposed

Suffolk County Sheriff Steven Tompkins had what he figured was a foolproof plan to make some quick cash in the booming cannabis industry.

The 67-year-old Massachusetts sheriff thought his badge gave him all the leverage he needed to force his way into a profitable investment deal.

But federal prosecutors just blew the whistle on Tompkins’ alleged extortion scheme – and the details are more outrageous than anyone expected.

According to federal court documents, Tompkins used his official position to shake down a Boston cannabis company executive for pre-IPO stock shares worth $50,000.¹

https://twitter.com/caldrm12/status/1954913499613687920

The scheme started in 2019 when an unnamed cannabis company needed Tompkins’ help to open a dispensary in Boston.

Massachusetts Cannabis Control Commission rules required the company to partner with the Sheriff’s Department to hire former inmates from their re-entry program.

That partnership gave Tompkins exactly the opening he needed.

Tompkins turned public service into personal profit

Here’s where this story gets really ugly.

Federal investigators say Tompkins pressured the cannabis company executive by reminding them he’d helped with their license application.

The executive understood the threat perfectly – cross the sheriff and lose the business partnership that kept their license valid.

So in November 2020, the executive caved and let Tompkins buy 14,417 shares at the discounted price of $1.73 per share for a total investment of $50,000.

When the company went public in 2021, those shares jumped to $9.60 each – suddenly worth about $138,403.

Tompkins must have thought he was pretty smart about then.

But the cannabis market had other plans for the corrupt sheriff.

By May 2022, the stock had crashed and Tompkins watched his paper profits evaporate.

Sheriff refuses to take his lumps like everyone else

Most investors chalk up losses to bad timing or market volatility. Not Tompkins. Federal prosecutors say he had a different idea entirely.

He demanded his original $50,000 back – every penny of it.

The executive knew exactly what would happen if they refused the sheriff’s demand.

Tompkins could end the partnership between his department and the cannabis company, which would jeopardize their state license and destroy their business.

So the executive paid up, sending Tompkins five separate checks between May 2022 and July 2023.

Some of those checks were labeled as “loan repayment” to hide what they really were – extortion payments to a corrupt law enforcement official.²

“What the Sheriff saw as an easy way to make a quick buck on the sly is clear cut corruption under federal law,” FBI Boston Division Special Agent in Charge Ted E. Docks said.³

The whole scheme shows how Democrats in positions of power think the rules don’t apply to them.

Pattern of corruption emerges

This isn’t Tompkins’ first brush with ethics violations.

In 2023, the Massachusetts Ethics Commission hit him with a $12,300 civil fine for violating the state’s conflict of interest law.

Those violations included creating a paid position for his niece and forcing his staff to run personal errands for him.

The guy apparently thought wearing a badge meant he could shake down anyone he wanted.

You’ve got a sheriff – someone who’s supposed to uphold the law – allegedly using his position to squeeze money out of private businesses.

U.S. Attorney Leah B. Foley nailed it when she said elected officials in law enforcement are “expected to be ethical, honest and law abiding – not self-serving.”⁴

But Tompkins apparently missed that memo during his 12 years as Suffolk County Sheriff.

He oversees about 1,000 employees and manages correctional facilities including Boston’s House of Correction and the Nashua Street Jail.

He’s looking at up to 20 years behind bars for each extortion count, three years of supervised release, and $250,000 in fines.

Good program, bad sheriff

The whole thing started with a decent idea.

Tompkins’ department was partnering with the cannabis company to help former inmates find work after getting out of prison.

Programs like this actually work – they give people a legitimate path forward and cut down on repeat offenses.

But somewhere along the way, Tompkins allegedly decided this partnership could make him some money too.

Suffolk County voters elected him to run their jail system and help rehabilitate offenders. They didn’t elect him to line his own pockets.

The FBI arrested Tompkins in Florida, where he was likely attending a conference for the National Organization of Black Law Enforcement Executives.

He’s scheduled to appear in federal court in Florida before facing the charges in Boston at a later date.

Tompkins’ attorney hasn’t responded to requests for comment, and the Suffolk County Sheriff’s Department declined to comment on the charges.

The Democrat sheriff thought he could use his badge to force his way into a profitable investment deal and then extort his money back when things went south.

Instead, he’s facing decades in federal prison for corruption charges that expose the rot at the heart of Democrat-controlled institutions.

Nobody gets to use their government job as a personal ATM.

That goes double for sheriffs, who are supposed to be the good guys.

Steven Tompkins is about to learn that federal prosecutors don’t care about his sheriff’s badge when he’s allegedly shaking down private businesses for personal profit.

¹ U.S. Attorney’s Office for the District of Massachusetts, “Suffolk County Sheriff Charged with Extortion,” Press Release, August 8, 2025.

² – ⁴ Ibid.