There’s something kind of icky about big blue city politics, especially one as immersed in virtue-signaling progressive wokeness as Michelle Wu’s Boston, wrapped as it is in the protective bubble coating of Governor Maura Healey’s blue as blue can be Massachusetts.
All that progressive ideology is technically meant to deliver, well, basically, a managed, inclusive, equitable lifestyle of enough of everything to live – but not too much of anything in case it causes someone else to go lacking – with proscribed manners and decorum to maintain the equilibrium of all, and keep the proverbial peace in the valley.
Which, of course, means none of it happens. The powers that be are constantly exercising their authority in arbitrary fashion as they adjust societal haves and have-nots through regulation and restrictions. Everything is based on capricious and interpretive measures of that same equity concept (as there is no ‘standard’), or to assuage the umbrage of one particular professional victimhood group at any given time.
Ruling over these servile citizens gives one an outsized sense of their importance in many instances, sadly, which eventually manifests in exuding entitlement, petty fascist behavior, outright graft, or all of the above.
In Mayor Wu’s case, she’s infamous for picking winners and mostly losers, either as aides (The famous chomping staff lovebirds), rock ’em, sock ’em department heads (The feisty black queer femme leader), or for being race-specific when she holds parties (she’s none too fond of colonizers), among myriad other gems like her sanctuary city stand and current fire cadet scandal.
Last week, another of her closest confidants found himself in a bit of a pickle that is casting even more glory on the mayoral term of Michelle Wu.
Steven Tompkins is the Suffolk County Sheriff, who handles Boston’s jail, and has been one of Wu’s closest allies, having booted ICE from that same jail.
He is steeped in Black Lives Matter and racial grievance ideology, going so far in 2020 as to call it ‘Our Rosa Parks moment’ and taking the proverbial knee.
Before members of the Suffolk County Sheriff’s Office took a knee Friday in solidarity with protesters seeking an end to racial injustice, Sheriff Steven Tompkins delivered an impassioned speech about how systemic racism has affected the incarcerated population.
“The criminal justice system isn’t broken. The criminal justice system was built to be punitive. It was built to punish people that committed crime. And I’m not saying that’s a wrong thing. What I am saying, though, is when you have arrogance, and ignorance, and racism matched up with any punitive endeavour, bad things happen,” Tompkins said.
At the same time that the earnest sheriff was taking a knee and posturing about systemic, it turns out he was busy shaking down a local cannabis company that was fixin’ to go public. You see, the upstanding…well, kneeling…public servant wanted to make sure he got in on the ground floor of what was gonna be big money.
And he wasn’t afraid to throw an elbow to do it.
…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.
…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.
Sadly, for Tompkins, he didn’t have Nancy Pelosi’s deft touch as a stock picker.
Only two years later, his investment tanked, as some stocks tend to do.
Where the rest of us have to suck it up and go away poorer and hopefully a little wiser, Tompkins went back to the cannabis company and demanded his orginal fifty grand back.
You know – OR ELSE.
The company gracefully complied in order to pull their weed out of the fire.
…By May 2022, the stock value fell and he lost money. Foley said that Tompkins demanded his $50,000 back and the company executive agreed.
The check was paid with a memo that read “loan repayment,” the prosecution said.
Somebody must have harbored an ill feeling or two, not to mention kept the canceled check, because last week, the feds came calling for Sheriff Tompkins and it was all about the weed deal gone to pot. They arrested the Sheriff
🚨 JUST IN: Boston’s top jailer might need a cell of his own.
Democrat Sheriff Steven Tompkins indicted for extorting a weed company for stock.
Feds say he used his badge to get rich — then demanded a refund when the stock tanked.
Now he faces 20 years.https://t.co/Wsq0dvsT3b
— Mass Daily News (@MassDailyNews) August 8, 2025
The man is accused of being just another entitled thug who let his position and power go to his head.
Sheriff Steven W. Tompkins, who serves as the Sheriff for the Suffolk County Sheriff’s Department, has been charged with extortion involving the purchase of an equity interest in a Boston-based cannabis company.
Tompkins, 67, of Boston, Mass, was indicted by a federal grand jury on two counts of Extortion Under Color of Official Right. He was taken into custody this morning in the Southern District of Florida and will have an initial appearance at 11:00 a.m. He will appear in federal court in Boston at a later date.
“Mr. Tompkins is a sitting Sheriff, responsible for over 1,000 employees, who was elected by the good people of Suffolk County. Today, he 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. His alleged actions are an affront to the voters and taxpayers who elected him to his position, and the many dedicated and honest public servants at the Suffolk County Sheriff’s Department. The people of Suffolk County deserve better,” said United States Attorney Leah B. Foley. “Public corruption remains a top priority for my administration and we will continue to investigate and prosecute anyone who uses their position of trust and power for their own gain.”
Now he faces a possible 20 years for every count of the indictment.
Tompkins didn’t exactly have a sterling reputation to begin with, having been on the radar for a while thanks to other obvious missteps.
…An indictment against Tompkins, who has served as sheriff since 2013, charged him with two counts of extortion under color of official right. Each count carries a maximum sentence of 20 years in federal prison.
Described as a “ubiquitous, glad-handing Democrat in Boston political circles” by the Boston Globe, Tompkins oversees the largest county correctional system in Massachusetts.
The sheriff has previously come under the scrutiny of authorities. In 2023, he paid a $12,000 fine for creating a no-bid job for his niece several years earlier and for asking subordinates to run personal errands. He also paid another $2,500 fine for asking business owners to remove his political opponent’s campaign signs from their windows.
Mayor Wu has made all the appropriate cooing noises about ‘Oh, very serious’ but nothing more than that so far.
The arrest is also going to bring heat down on the MA pot industry, which has had its own issues since being legalized in 2016. No one will be thanking the sheriff for acting like a mob boss in the least.
…Tompkins’s indictment is likely to cast a spotlight on Massachusetts’ legalized marijuana industry, which has come under scrutiny since the state legalized the drug in 2016. Two years before Tompkins’s arrest, Massachusetts formed a Cannabis Control Commission after a series of scandals, including the dismissal of its top commissioner for bullying and making racially inappropriate comments.
Which has led to its own speculation about Tompkins and his fervent anti-ICE crusading as sheriff.
Let’s sweat Tompkins for his ties to the cartels.
Only reason for these “sanctuary sheriffs” is for their connections to people who are way more powerful and scary.
— Kurt Nimphius’ Hair (@Hcp1Hcp) August 8, 2025
Just another day in Beantown.
…”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,” said Ted Docks, Special Agent in Charge of the FBI in Boston.
Brian Kelly of the law firm Nixon Peabody is former chief of the public corruption unit at the Boston U.S. Attorney Office. He said Tompkins has a tough defense to make.
“I’m sure he’ll have some sort of defense or explanation as to why he wasn’t shaking down a company, which is essentially the charge, shaking down a company for his own benefit,” said Kelly. “And if that’s what the facts show, he’s got a problem.”
I’ll stick my neck out here and take ‘He’s got a problem‘ for $500, Alex.
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