Spotlight: A real mess in the sheriff's office

 

September 12, 2025 Gordon Russell Deputy Spotlight Editor 📥 gordon.russell@globe.com For years, Suffolk County Sheriff Steven Tompkins has been a ubiquitous presence at campaign events for Massachusetts Democrats, but has otherwise kept a pretty low profile. That changed last month when he was charged by a federal grand jury with two counts of extortion. In today's newsletter, we take a deeper dive into Tompkins's career — and a series of financial moves he made starting in 2020, when he invested in a cannabis firm. Amid Tompkins's legal troubles, we also recently traveled back in time to 2002. The same office was under fire after Spotlight stories and FBI investigations revealed that the Suffolk sheriff — like Tompkins, an appointee with little correctional experience — was rarely at the jails he oversaw and that problems were festering. Sound familiar? As always, send tips and feedback to spotlight@globe.com. Our latest Suffolk Sheriff Tompkins's weed investment cratered amid expensive re-election campaign Craig F. Walker/Globe staff Andrew Ryan Spotlight Reporter 📥 andrew.ryan@globe.com Danny McDonald Metro Reporter 📥 daniel.mcdonald@globe.com Five years ago, longtime Suffolk County Sheriff Steven Tompkins had every reason to think he was looking forward to a lifetime of easy reelections. Nearing retirement age, he held a post many Boston voters are scarcely aware of that paid him around $190,000 a year. But a lot changed for Tompkins in a short period of time. He invested a chunk of his nest egg into a cannabis company, and then refinanced his home in Hyde Park, taking on significant additional debt. Days later, he bought a half-million-dollar rental property in Roxbury.   On the very same day that purchase closed, one of his top aides announced she was running against him—a stiff challenge that prompted Tompkins to put up tens of thousands of dollars of his own money to fight off. Soon, the value of his stake in the weed company was in free fall. And that’s when Tompkins doubled down on what prosecutors say was already an illegal deal and demanded that the owner of the cannabis company refund his $50,000 investment. Now, Tompkins faces charges that could put the longtime jailer behind bars himself. Last month, a federal grand jury indicted the sheriff on two counts of extortion for allegedly using the power of his office to strong-arm the cannabis company. Read Now Related ‘Is that the look you want to give?’ Suffolk Sheriff Steven Tompkins relies heavily on employees for campaign donations Longtime Boston lobbyist, pot entrepreneur is alleged extortion victim of Suffolk Sheriff Is this what happens when a governor picks the sheriff? Craig F. Walker/Globe staff Andrew Ryan Spotlight Reporter 📥 andrew.ryan@globe.com Danny McDonald Metro Reporter 📥 daniel.mcdonald@globe.com A governor appoints a sheriff with zero experience in law enforcement. Soon enough, the office is mired in allegations of malfeasance. It’s déjà vu in Suffolk County. Two decades ago, the then-sheriff of Suffolk County, Richard J. Rouse, resigned after the Globe Spotlight Team and the FBI revealed physical abuse by his guards, runaway nepotism in his hiring, and chronic mismanagement at his office. This time, it’s Steven W. Tompkins who is accused of wrongdoing, pleading not guilty to two charges of extortion and announcing he would step away while the federal case is ongoing.   Read Now From around the newsroom DOJ lawyer in Harvard case once wrote a paper from Hitler’s perspective Michael Velchik, when he was a senior at Harvard 14 years ago, submitted a paper for a Latin class written from the perspective of Adolf Hitler. (Read more) Mass. GOP to pay $36,000 to settle allegations it took thousands in illegal donations in 2022 The agreement marks at least the fourth settlement state GOP leaders have entered into since 2023 to resolve disputes or allegations stemming from their actions in past election cycles. (Read more) Have a tip about wrongdoing, corruption, or injustice? The Globe Spotlight Team wants to hear from you. Click here to send us an email. What we are reading The New York Times Magazine How JPMorgan Enabled the Crimes of Jeffrey Epstein A Times investigation found that America’s leading bank spent years supporting — and profiting from — the notorious sex offender, ignoring red flags, suspicious activity and concerned executives. (Read more) ProPublica / WBUR After 17 Years, DNA Tied a Man to Her Rape. Under Massachusetts Law, It Was Too Late. Massachusetts law says prosecutors have only 15 years to file charges after an alleged rape. This statute of limitations places Massachusetts behind almost every other state in the country. (Read more)

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