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.
Tompkins, 68, has pleaded not guilty and taken medical leave from his post. His attorney, Martin G. Weinberg, said Tompkins will defend himself “in a future trial before a jury of the sheriff’s peers and not in the media.”
An early stumble
Tompkins first came into the sheriff’s office in 2013 when he was appointed to replace his boss, who had accepted a position in then-Governor Deval Patrick’s Cabinet. But the ink was hardly dry on his commission when a number of store owners in Roxbury complained he had flashed his new badge at them and pressured them to take down signs supporting his opponent in the upcoming election.
The State Ethics Commission fined him $2,500, and Tompkins said he’d “learned from the experience” and wouldn’t slip again. But Tompkins found himself in the commission’s crosshairs a second time after he created a taxpayer-funded job for a niece a few years later, and had her and other employees do errands and other personal business for him.
Globe interviews with eight former and current subordinates, as well as public records, paint a picture of a sheriff who was more interested in the trappings of the office than in the running of it, and who spent heavily on travel and other perks.
Those employees said Tompkins is seldom if ever seen at the Nashua Street jail, which along with the House of Correction is one of the two main facilities the sheriff oversees. Over the past five months — the full span of available records — Tompkins never swiped his access card at the jail, according to records the sheriff’s department provided in response to a Globe request.
While employees describe Tompkins as an absentee boss, he has been a longtime fixture at Democratic Party events, and his resume is heavy on politics and light on law enforcement; in fact, when Patrick appointed him sheriff, he said that was what drew him to Tompkins.
“It’s a political job, so the folks that are criticizing it as a political hire, tell them: They’re right,” Patrick said at the time.
But unlike many Boston pols, Tompkins wasn’t born here. He was raised in Harlem by a single parent on public assistance, he has said, describing his youth as “hard-knock.”
Tompkins came north to Boston College, where he was a classmate of Cabral, who would hire him when she became sheriff in 2002. After graduation, Tompkins worked a variety of jobs, including at AT&T’s cable division and the Federal Emergency Management Agency and a stint as director of marketing and public affairs for the Dimock Community Health Center in Roxbury.
He became more politically active, landing a position with the local branch of the NAACP and serving on various boards: the Sportsmen’s tennis club, the youth-focused nonprofit City Year, the fiscal watchdog known as the Boston Finance Commission, and more.
Affable and chatty, with a wide smile, Tompkins became a regular at Boston political events. He would sometimes show up at rival rallies, giving the impression he supported both camps.
In 2013, while attending an event for US Representative Stephen Lynch’s Senate bid, the newly minted sheriff parroted the tagline from the candidate’s ad: “We are all Stephen Lynch.”
Tompkins had also appeared at an event for Lynch’s rival, then US Representative Edward Markey, prompting both campaigns to tout his support. When asked, the sheriff hedged his bets.
“I wasn’t with either candidate,” Tompkins told the Dorchester Reporter.
In 2016, Tompkins made an unsuccessful bid to be chairman of the Massachusetts Democratic Party, a campaign he had to pause briefly because of the sudden death of his wife.
The sheriff’s Facebook page is a who’s who of Democratic politics. There’s a picture of Senator Elizabeth Warren speaking at a 2014 Tompkins campaign event with future Mayor Michelle Wu looking on. A 2017 image shows Tompkins in a top hat with Facebook founder Mark Zuckerberg and Middlesex Sheriff Peter J. Koutoujian. There’s Tompkins with Mayor Martin J. Walsh at Fenway Park in 2018, and more recent shots with Governor Charlie Baker and his successor, Maura Healey.
In 2018, Boston Magazine named Tompkins No. 76 on its list of the 100 most influential Bostonians, saying the sheriff had “quietly become one of the most popular elected officials in Boston.”
In short, in the world of Boston politics, everybody knew Steve. And many like him — though many are loath to talk about him in the wake of his indictment.
A couple of exceptions: state Senator Lydia Edwards, an East Boston Democrat, who considers Tompkins a friend. She described him as “funny, loyal, good guy.”
“I’m withholding all judgment,” she said of his current predicament. “I don’t dance on my friend’s grave.”
Michael Curry, former president of the Boston branch of the NAACP, recalled seeing Tompkins work the room this year at the Reggie Lewis Center during the Brothers IV Breakfast, a community event intended to foster fellowship. Tompkins tried to connect with every young person in the room, he said.
Curry described Tompkins as “always available, a people person who leads with humor.”
Former state treasurer Steve Grossman, whom Tompkins has supported in past political campaigns, described the sheriff as “popular, well liked, and well regarded.”
Like Edwards, Grossman said Tompkins was owed due process.
“You can understand why people are grieving over this,” he said. “And why people across the political spectrum are not rushing to judgment. People don’t want the charges to be true.”
‘Comfort and complacency’
For some erstwhile Tompkins supporters, the sheriff lost his luster well before his indictment.
Paul Parara, better known as the Notorious VOG, a local radio host who interviews politicians for a primarily Black and brown audience, noted that early in his tenure as sheriff, Tompkins talked forcefully about rehabilitating inmates. Indeed, at the sheriff’s office, Tompkins helped create a vocational training program for inmates about to be released.
But Parara doesn’t believe those efforts have amounted to much, and he recently called on Tompkins to resign.
“Tompkins once spoke of reform and rehabilitation,” he said. “But today he represents the comfort and complacency of the system.”
But Curry had a different take, recalling how Tompkins had helped steer the NAACP’s messaging on policing, community violence, education, and the economy. He described the sheriff as “super knowledgeable . . . always committed to community and social justice issues.”
Curry has had Tompkins in to speak to his students at New England Law | Boston, where Curry is a lecturer, and said the sheriff focused on reentry rather than incarceration, and posed societal questions: “How do we understand what are the conditions that made young people and people in general commit crimes?”
It was Tompkins’s reentry program that is at the heart of his current legal troubles. Ascend Wellness Holdings, a cannabis firm, struck a partnership with the sheriff’s office to hire former inmates as part of its licensing process. Prosecutors allege Tompkins used the deal as leverage to buy a stake in the firm.
But it appears Ascend was unable to hire any of the former inmates the sheriff steered its way, according to a sheriff’s department spokesman and email correspondence obtained by the Globe through a public-records request. Ascend did not respond to messages from the Globe.
Parara isn’t the only observer who accuses Tompkins of doing little to help those in his care.
Janhavi Madabushi, director of the Massachusetts Bail Fund, which lobbies for less restrictive conditions for the accused, tends to be broadly critical of sheriffs. But he singled out Tompkins in particular, saying he “co-opts progressive language and buzzwords” to make it seem like he’s an advocate for the downtrodden when his main interest is “political power.”
In 2021, Tompkins proposed a portion of an unused Suffolk County detention center be repurposed to house people who struggle with homelessness, drug addiction, and mental health problems in the drug-plagued neighborhood known as Mass. and Cass. Some other public officials criticized the idea as inhumane, and though it was the subject of intense discussions, it never got off the ground.
On the other hand, Tompkins was an early critic among law enforcement officials of the war on drugs. In a 2016 panel discussion, he called the effort a “flaming joke,” complaining that kingpins tended to skirt arrest, and saying it had mostly resulted in young men of color spending years behind bars.
Despite those progressive views, Tompkins wasn’t ready to legalize marijuana. When Massachusetts was preparing to vote on the question in 2016, Tompkins led a group of Massachusetts sheriffs in denouncing the idea.
“As a Commonwealth, we need not take actions that could increase availability to, and use of drugs among, young people,” Tompkins said at the time. “If this referendum were to pass, Massachusetts would surely see an increase in the amount of marijuana use and addiction.”
Four years later, Tompkins was angling to get into the pot business.
Milking the office
According to prosecutors, sometime in 2020, Tompkins told Frank Perullo of Ascend — the businessman and lobbyist he is now accused of extorting — that “he wanted to get in on the stock so [he] could make some cannabis money.”
Perullo allowed him to invest in Ascend in November 2020, when the company was still privately held; Ascend went public in May 2021, and initially its stock rose. Tompkins’s $50,000 stake came from a retirement account, according to the indictment.
Records show Tompkins made another significant investment a few months after Ascend went public, adding to his debt. On Jan. 5, 2022, he bought a property in Roxbury for $550,000, putting 25 percent down. Weeks earlier, he had refinanced the debt on his primary home, in Hyde Park, taking out a much bigger loan on it.
The same day Tompkins closed on the Roxbury property, Sandy Zamor-Calixte, the sheriff’s chief of external affairs, announced she was running against him. Zamor-Calixte, who declined to comment for this article, eventually received 41 percent of the vote.
In the face of that challenge, Tompkins ended up loaning his campaign a total of $67,500 in personal funds — a bit more than the value of his holdings in Ascend. It took him nearly two years to raise the money to pay himself back.
Throughout the campaign, his stake in Ascend was losing value. Tompkins demanded to be made whole, according to the indictment.
By the end of 2022, Perullo had returned nearly all of Tompkins’s $50,000 investment. His shares were worth less than $17,000 at that point.
Over Tompkins’s tenure, meanwhile, state credit card records for the office suggest a growing department spending habit on restaurants, conferences, and junkets.
During the last fiscal year, the Sheriff’s Department spent more than $133,000 using the card, a tally that covered trips for multiple employees to visit Austin, Texas; New Orleans; Baltimore; Washington, D.C.; the Bahamas; and Martha’s Vineyard.
Last year’s spending on the office credit card — which typically is used for travel, meals, and miscellaneous items — was more than five times the amount billed to it a decade earlier, when Tompkins was still new to the job. Records provided to the Globe thus far are incomplete, but show that Tompkins traveled frequently on the card.
On Aug. 8, Tompkins was on one of the trips billed to the card. He was arrested by FBI agents in Hollywood, Fla., while attending the annual conference of the National Organization of Black Law Enforcement Executives, or NOBLE. Tompkins was a regular at the group’s annual meetings, records show, and two NOBLE leaders say he was instrumental in establishing its current state chapter.
Renée Hall, NOBLE president, said Tompkins currently does not hold any leadership positions there. She said she had no “personal thoughts” about Tompkins’s arrest and indictment.
“If he is found to be on the other side of the law, then he should, like anyone else, be held accountable,” she said. “Until that happens, we support him as a member.”
Jeremiah Manion and Matt Stout of the Globe staff contributed to this report.
Danny McDonald can be reached at daniel.mcdonald@globe.com. Follow him @Danny__McDonald. Andrew Ryan can be reached at andrew.ryan@globe.com or via the encrypted messaging app Signal at @andewryan.61