Everything we know so far about the cannabis industry relationship that led to the arrest of the Suffolk County, Massachusetts sheriff for alleged extortion
The indictment of Suffolk County Sheriff Steven Tompkins for alleged extortion of a cannabis company is truly explosive. Some might even describe last week’s epic arrest as tragic under the circumstances. As well as a massive blow to the national rep of a state where a South Coast mayor was already sent to federal prison for seemingly similar solicitations.
The US Department of Justice announced the Tompkins indictment on Friday. He was taken into custody in Florida, where the sheriff was in town for the National Organization of Black Law Enforcement Executives’ annual training conference. Tompkins previously served as the vice-president of his regional chapter of NOBLE, one of many leadership positions he took on while rising to his current elected spot.
But while this is an unexpected and unfortunate occurrence from some angles, or even a baseless attack on a leader of color by a DoJ that is hellbent on crucifying the Bay State, the full picture emerging is far more complex. And potentially uglier.
At this point, many questions remain beyond the quite detailed Aug. 7 indictment and accompanying press release. First and foremost, there’s the identity of “Company A” that is named in the indictment. That appears to be Ascend Wellness Holdings (AWH), a New York-based multi-state operator with three retail locations in Mass including one in Boston’s North Station. The indictment charges that Tompkins pressured a cannabis company to cut him $50,000 in checks after the candy sweet stock deal he had already finagled went south. Tompkins vouched for AWH (and no other Cannabis Control Commission applicants) on multiple licensing applications going back to 2019. In one letter, he wrote that Ascend was part of a program in which the sheriff’s department “trains and prepares candidates for employment and regularly works with employers who are willing to hire them.”
The Tompkins indictment also raises questions about how much damage this kind of high-profile hammering could do to the social equity focus of our state’s cannabis program. Especially as the arrest incites a rabid rightwing that’s salivating over the detainment of a sanctuary sheriff. It will take some time to fill those gaps. For now, here’s everything we know, based on public documents and conversations with multiple sources familiar with different elements of the elaborate saga.
The sheriff and the spokesperson
Steven Tompkins doesn’t have a law enforcement background. Aside from on-the-job training and professional development (for example, he’s listed on the roster for a 2016 Massachusetts counter-terrorism seminar in Israel sponsored by the Anti-Defamation League), his experience is in media and public affairs. Long before taking over the jails in New England’s largest city, he worked as the marketing director for a community health center and before that as a TV producer.
Per his bio, as the chief of external affairs for the sheriff’s department, Tompkins “supervised his own division and was a member of his predecessor’s nine-person Executive Team, which was responsible for the day-to-day management of all operations.” He called that predecessor, Andrea Cabral, a “dear friend” who introduced him to sheriff work. The two attended Boston College together in the 1980s, and Tompkins’ work helping run the department under Cabral paid off. He didn’t even have to campaign, but rather was appointed sheriff by then-Gov. Deval Patrick in January 2013 after Cabral was tapped for an executive safety role in the Patrick administration.
“As a dedicated public servant on the frontlines of crime prevention and reentry rehabilitation, Steven brings first-hand knowledge and passion to this critical position,” the governor said in a statement. “I am confident in his ability to serve Suffolk County in this role and I look forward to working with him to strengthen our re-entry programs and reduce youth violence.”
“Steve brings an extraordinary level of relevant prior experience to this position,” Cabral said. “His job required him and his staff to work with every division within the Department. He knows what it took to get us where we are and he is very committed to building on that progress. Under his leadership, this Department’s best days are ahead of it.”
Protecting (and flashing) the badge
Defending his appointed seat in the 2014 county election, Tompkins won major endorsements from the likes of Boston Mayor Marty Walsh and US Sen. Elizabeth Warren, the latter of whom Tompkins worked for as a senior advisor during the senator’s 2012 race. He also scored the unprecedented backing of the unionized officers at the Suffolk County House of Correction.
Tompkins crushed the opposition, winning more than 60% of the vote in a three-way election, though his campaign tactics caught the attention of the State Ethics Commission. In 2015, he signed a disposition agreement with the commission and “paid a $2,500 civil penalty for invoking his position as sheriff when requesting store owners to remove his election opponent [Doug Bennett’s] campaign signs.”
Tompkins has found further troubles in the years since—all of it seemingly warranted, and notably more than your average Mass sheriff. He’s tangled with the ACLU and opioid harm reduction advocates for his proposals for Boston’s drug-ridden Mass and Cass corridor near the South Bay House of Correction under his watch. In 2021, GBH reported that five people had died in Suffolk County Sheriff’s Office (SCSO) custody in just six months.
Politically, Tompkins ran into additional trouble with state ethics watchers in 2023. In the second go around, the commission penalized the sheriff $12,000 for “creat[ing] a paid state job for his niece and [having] subordinate employees run personal errands for him during their paid public work hours.”
Per the media release: “In addition, by creating the paid state position which enabled his niece to stay in Massachusetts to assist him with the care of his children, financially benefitting both himself and his niece, Tompkins violated the conflict of interest law’s prohibition against public employees using their official positions to obtain for themselves or others substantially valuable unwarranted privileges. Tompkins also violated this prohibition by requesting and allowing members of his staff to provide him with substantially valuable assistance with his private matters during their paid public work hours.”
The sheriff turned cannabis CEO
I interviewed Andrea Cabral at the May 2021 grand opening and media spectacle for Ascend in North Station. By then, she’d been retired from public service for about three years, making appearances on GBH radio and helping establish Ascend in the background.
It was an extremely masked COVID era affair, and so even ganja glitz and glamor cynics like me were thrilled to be out in public to see what was advertised as an Apple Store-like dispensary just steps from TD Garden. Sleek and staffed by knowledgeable budtenders, the spectacle was certifiably impressive. As was its Massachusetts CEO, who convinced me that she wasn’t just another hypocritical former official trying to cash in on weed.
As an ex-prosecutor who was chief of the Suffolk County District Attorney’s Office Domestic Violence Unit prior to becoming sheriff, Cabral said she had thought about these issues since long before she teamed up with Ascend.
“I don’t drink, I never have,” she said in our interview more than four years ago. “I just don’t like the taste of alcohol. But I have spent a career seeing what alcohol has wrought in the lives of people.” “By comparison,” she added, “cannabis, which does none of these things, is demonized and stigmatized and in some cases overly regulated. So it wasn’t that big of a leap for me to do this.”
During the ribbon-cutting ritual on Friend Street, Cabral spoke of high hopes for Ascend to be “a model for how this cannabis industry was created and grew in Massachusetts, especially around social equity.”
She delivered the same message five months later as the guest on Real Talk in the Commonwealth, a pod-and-web cast hosted by Tompkins and distributed by his department. After a friendly introduction and glance down memory lane, the sheriff asked her about her turn toward the pot biz.
“I got a call from your friend and mine, Frank Perullo, who was my political consultant back in the day and I believe has done the same for you,” Cabral told Tompkins. “He said he and another guy were starting a cannabis company [Ascend] … and asked me if I was interested in coming on board. I thought, Why not? I knew something about the cannabis industry because the medical regulations were put in place while I was still secretary of public safety.”
Cabral, who was also an early appointee to the CCC’s Cannabis Advisory Board, continued: “It started from there. Three, then four, then five people in a room, and now it’s a multi-state operator with three retail locations [in Massachusetts].”
After speaking about issues spanning politics to prisons, Tompkins thanked Cabral for coming on, telling his predecessor: “Enjoy your new position and what you’re doing and make lots and lots and lots and lots of friends and money.”
Common Ground Institute
When Deval Patrick appointed Tompkins to fill Cabral’s vacant seat, the governor touted the new sheriff’s creation of the “innovative ‘Common Ground Institute,’ a vocational training program that prepares inmates for and finds them post-release employment.”
An audit of the Suffolk County Sheriff’s Department conducted in 2019 showed that the program endured. It recognized the institute as providing “instruction in carpentry, landscaping, gardening, roofing, building maintenance, painting, OSHA-30, [and] Financial Planning.”
The report by the Commission on Accreditation for Corrections added: “It was a pleasure to tour the educational areas as the students were observed to be attentive to their instructors. The classrooms were well-lit, organized, and furnished with appropriate learning spaces and materials.”
Around the same time, Ascend entered a relationship with the department “whereby the [SCSO] would help screen and refer graduates of its re-entry program to apply for work at [AWH]’s retail store. [AWH]’s partnership with the [SCSO] was memorialized in a September 2019 letter signed by Tompkins and submitted to the CCC in its completed dispensary license application in or about March 2020.”
And so on, and so forth. It’s your typical sheriff teams up with a cannabis company, then pressures its principals for stock, wins, loses his shirt, demands his initial investment back, and winds up back at zero and indicted kind of story. Nothing that we haven’t seen before.
“Tompkins paid a pre-IPO price of approximately $1.73 per share … and after a reverse stock split, Tompkins held approximately 14,417 shares at a price of approximately $3.46 per share.
“According to court documents, in or about mid-2021, when [AWH] launched its IPO, the stock had a value of approximately $9.60 per share. Thus, Tompkins’s $50,000 purchase of 14,417 shares of [AWH] stock had appreciated to an approximate value of $138,403.
“In May 2022, [AWH] stock decreased in value such that Tompkins’s equity interest in [AWH] stock was worth several thousand dollars less than the $50,000 he originally invested.”
The indictment alleges that five checks were cut to reimburse Tompkins between May 2022 and July 2023. By then, Ascend appeared to be descending. In September 2022, the company’s national CEO was arrested in South Florida for an alleged domestic violence incident. Those charges were dropped days later due to a lack of cooperation with authorities, but there was apparent PR damage, all while the stock had been sliding for more than a year.
Around the same time, Cabral left AWH. Emails to the former Suffolk sheriff’s Ascend account bounced as early as Oct. 25, about a month after those headlines hit.
Innocent until proven guilty
The DoJ’s indictment tells a version of the story above in a light of its own color.
“From his very first day as Suffolk County Sheriff, Steven Tompkins sought to portray himself as a man of the people – a principled public servant and reformer, devoted to the cause of justice,” Ted E. Docks, Special Agent in Charge of the Federal Bureau of Investigation, Boston Division, said in a statement. “That’s why it’s beyond disappointing that he’s now accused of gaming a system instituted in the interests of public safety and fair play.”
The tone of the prosecutors is showy and harsh. Which seems fitting for the Trump justice department, but really that’s how every state and federal attorney gloats during the perp walk. If you can ignore for a moment how the DoJ is currently focused on persecuting the president’s perceived foes, and simply consider the facts presented by 47’s US attorney in Mass Leah Foley, it comes off like a standard condemnation.
“Public corruption remains a top priority for my administration,” Foley said. “We will continue to investigate and prosecute anyone who uses their position of trust and power for their own gain.”
