BOSTON — Looks like Suffolk County’s top jailer may need a jail cell of his own.

Sheriff Steven Tompkins, a longtime Democratic fixture in Boston politics, was arrested Friday in Florida on federal extortion charges tied to a shady stock deal with a local cannabis company. Prosecutors say he leveraged his badge for a bag — and got caught.

Weed, greed, and a $50K shakedown

According to U.S. Attorney Leah Foley, it all started in 2019 when a cannabis company partnered with the Suffolk County Sheriff’s Department to hire former inmates. Good PR, good politics — and apparently, good leverage.

But by 2020, prosecutors say, Tompkins pulled a fast one: give me stock… or your license might “accidentally” go up in smoke.

Sheriff “invested” in pot — then cried foul when the stock crashed

Tompkins paid $50,000 out of his retirement fund to buy shares just before the company’s IPO. When the stock hit Wall Street at $9.60 per share, his stake ballooned to over $138,000. Not bad for a side hustle in uniform.

But like every Massachusetts political scheme, the gravy train derailed.

The stock plummeted. Tompkins lost money. So, according to prosecutors, he demanded a refund — and got it. The company cut him a check labeled “loan repayment.” Investigators say it was anything but.

From lawman to bagman?

Tompkins now faces up to 20 years in prison, plus supervised release and a $250,000 fine. Translation: he could end up serving more time than half the inmates he books.

This is the same sheriff who loves TV hits, equity panels, and social justice speeches. But behind the scenes? Feds say he was bullying a weed startup into a backdoor payday.

How the scam allegedly went down:

2019: Dispensary partners with sheriff’s office to hire reentry grads

2020: Tompkins pushes for stock ahead of IPO

2021: IPO hits, stock skyrockets, Tompkins profits

2022: Stock crashes, Tompkins demands refund

2025: Feds pounce — and the mugshot era begins

Will Michelle Wu comment? Don’t hold your breath

Tompkins has been one of Mayor Wu’s most visible public safety allies — but now he’s the face of a federal indictment. No comment yet from Wu, Suffolk DA Kevin Hayden, or the Cannabis Control Commission.

Yet another Massachusetts Democrat goes up in smoke

Massachusetts has seen its fair share of shady Democrats — from bribe-taking reps to City Hall bathroom cash drops. But shaking down a weed company while running the county jail? That’s a new one.

If convicted, Tompkins could spend his golden years not at Nashua Street Jail — but in a federal cage of his own.

This is a developing story.