Steven Tomkins: Public Office, Private Gain

0:00You may have heard of the sex cult NXIVM and the famous actress who went to prison for her involvement, Alison Mack. But she's never told her side of the story, until now. People assume that I'm like this pervert. My name is Natalie Robamed, and in my new podcast, I talk to Alison to try to understand how she went from TV actor to cult member, and what she thinks of it all now. How do you feel about having been involved in bringing sexual trauma to other people? I mean, I don't even know how to answer that question. Alison, after NXIVM from CBC's Uncover, is available now, wherever you get your podcasts.

0:43Anyone who wants to be anyone has a podcast these days. And yes, that includes your local sheriff. If you live in Suffolk County, Massachusetts. Sheriff Stephen Tompkins hosts the podcast Real Talk in the Commonwealth on behalf of the Suffolk County Sheriff's Department. Hello and welcome to Real Talk in the Commonwealth. I'm your host Suffolk County Sheriff Steve Tompkins. In a video clip from the podcast posted in October 2021, Tompkins sits in his office, trophies and honors arranged in the background. A small silver sheriff's badge glints on his lapel. Tompkins has an easy demeanor, laughing while he interviews his friend and mentor, Andrea Cabral, the former sheriff of Suffolk County and current CEO of Ascend Wellness, a cannabis company.

1:36One topic they discuss on this podcast is the possibility of federal cannabis legalization. These two people definitely have interesting perspectives on the matter. Both have served as sheriff of Suffolk County, a position that would often place them at odds with recreational drug users. But Andrea Cabral made an unexpected career shift when she moved directly from law enforcement to the cannabis industry. As they sign off from the interview, Tompkins says goodbye to Cabral and, in reference to her new business venture, says this. So with that said, you know, go forward and prosper and all that good stuff.

2:17Live long and have a good time and enjoy your new position in what you're doing and make lots and lots and lots and lots and lots of friends and money. Sounds like Sheriff Tompkins has a good idea of where the money is. In fact, he sounds positively giddy talking about making money. Would you want your elected official to sound that excited about profit to be made from the cannabis industry? The FBI released a statement saying we believe that the sheriff saw an easy way to make a quick buck on the sly. Four years later, Tompkins' podcast episode sounds less like local government outreach and more like a red flag.

3:05Suffolk County Sheriff Stephen Tompkins now finds himself on the other side of the law. On Friday, the 67-year-old was indicted for allegedly extorting a Boston cannabis company.

3:20This is The Opportunist, an original podcast from Podcast One. You're listening to a story told in one episode called Sheriff Stephen Tompkins Caught with a Smoking Gun. I'm Sarah James McLaughlin. In this episode, we dive into the story of Sheriff Stephen Tompkins, an ambitious public servant who might have finally found himself embroiled in a scandal he can't talk his way out of.

3:58Any Boston area native with an interest in local politics would know the name Sheriff Stephen Tompkins. He was appointed Suffolk County Sheriff in 2013 and has held the post continuously until 2025. Here's Dan McDonald, a reporter for the Boston Globe. Suffolk County is where the city of Boston is located. There's a handful of other communities, but it's dominated by the city of Boston. While you might think of the elected position of sheriff as a high-stakes political role, the sheriff in the city of Boston is a pretty behind-the-scenes gig. Sheriff's offices in Massachusetts are a bit of a political backwater.

4:42It's not like other parts of the country, particularly the South, where sheriffs have a lot of political power. I mean, basically they're there to run the jails. The Suffolk County Sheriff maintains the South Bay House of Correction and the Nashua Street Jail and is responsible for 1 ,000 correctional officers, as well as both sentence inmates and those still awaiting trial. Running the jails means more than just housing inmates. It entails caring for their mental health, their physical well-being and safety, and providing educational resources. According to the Suffolk County Sheriff's website, the sheriff is committed to giving inmates the tools to reenter their communities with better opportunities as contributing citizens.

5:31Maintaining a safe and effective jail system that serves the community and hopefully reduces crime is a noble job. But the lack of a spotlight on this position appears to have had a less than noble effect on the sheriff's office. In the murky depths of a political backwater, opportunities for corruption abound. As in many corners of Massachusetts politics, there's a lengthy and well-documented history of corruption amongst Massachusetts sheriffs. So there's been allegations of bribe-taking, allegations of extortion. There's a history of chronic mismanagement at some of the sheriff's offices and pretty brutal accusations of sexual exploitation and brutality on behalf of the jail guards.

6:20In a democratic system, our greatest power is our vote. For high-stakes ballots, like federal presidential elections or state gubernatorial races, voters ideally give a lot of thought to their choice. If they're really on top of it, they listen to the news, read articles, and scrutinize the candidates before making an informed vote. And by doing so, they hold their leaders accountable. But what about the local races that are further down on the ticket? Unless you make the following local politics a special hobby, it can be easy to show up to the ballot box uninformed about the candidates running for an office like the sheriff.

7:04I've talked to the proverbial gadflies and political observers, and they seem to suggest that the fact that this is an obscure office and basically the only mechanism for accountability is the ballot box every six years. And other than that, people aren't really checking under the hood, so to speak, of like how things are working. And even at the ballot box, people are concentrated on the statewide races, the municipal races like mayor and city council. It's not a top of mind issue. Some people say that because it's so obscure and there isn't a lot of accountability, that has led to the proliferation of corruption.

7:48It's into this low oversight, high corruption environment that Tompkins entered the scene in 2013. So Steve Tompkins has been Suffolk County Sheriff since 2013. In that role, his main job is to oversee two jails in the city of Boston, Nashua Street and South Bay. The inmates in those facilities include folks who are awaiting trial, as well as folks who have already been sentenced. He came to the position, basically the former sheriff was tapped for a state-level public safety job, and he was appointed by the governor. And then he subsequently has won re-election a few times. In his own words, here's how Tompkins describes his rise into public office.

8:44The way I became sheriff is this. I worked for the prior sheriff, Sheriff Cabral, who has gone on to work for the governor. She is now the secretary of the executive office of public safety. And so when she was leaving, I talked to her and I talked to the governor and some of his folks about the possibility of me replacing her. And I was fortunate enough to be tapped to become the 31st sheriff of Suffolk County. To be clear, Tompkins was not elected by the people into the sheriff's office in 2013. He talked his way into it. From that point, it was easy to gain re-election because his name was already on the ballot as the incumbent.

9:24And for those that actually knew who Sheriff Tompkins was, he was easy to vote for. He used his position as sheriff to gain entry into the Massachusetts Democratic Party political scene and became a well-liked local character. He's just kind of known as this kind of glad-handing, sort of back-slapping politician who's well-liked in political circles. He's known as kind of being like this friendly, avuncular presence. He just has this reputation, amongst other polls, of being a really friendly guy who returns calls. And again, he's heavily involved in Democratic politics. He ran to be chairman of the state committee.

10:08So he's known, even though there is a cap on how much power he has, because he's sheriff, right? So he's kind of known as this guy that's just kind of around, I guess. Tompkins had a good handle on which Massachusetts politicians were at the cool kids' table and regularly made an effort to be seen with them. He was a campaign advisor to progressive Massachusetts Senator Elizabeth Warren and has been spotted going to Celtic games with Michelle Wu, Boston's mayor. His alignment with progressive causes extended into his tenure as sheriff. One of Tompkins' main talking points when it came to the sheriff's office was his programs to reduce recidivism in Boston-area jails.

11:00Recidivism is the tendency of a convicted criminal to re-offend. In other words, to stay in the system. A low rate of recidivism means that there is less repeated crime, more rehabilitated citizens, and indicates a successful penal system. This is Sheriff Tompkins explaining his perspective on the role of the sheriff's office. We're in the second chance business, okay? A lot of people do things and they get themselves in trouble. Some folks should go away for a long time. Some folks should just pay their debt to society and then be given a second chance to get out there and take care of themselves and their families.

11:39And so that's really kind of what my mission and my passion is. One, to safeguard the citizens of Suffolk County. But then after that, I'm looking at education, talking to kids about not going to jail, you know, and then when the guys get out, looking at what we call reentry, when you leave and you go back into society, hoping that they can go back into society a little bit stronger, a little bit wiser, and a little bit better than when they left so they don't come back to visit us. in public Tompkins was a perfect non-threatening politician he smiled and laughed for the camera and supported initiatives that raised up at-risk communities he believed strongly in second chances but behind the scenes Tompkins could be a smooth talker and social climber consistently constantly pushing the limits of his power and arguing his way out of consequences.

12:31To put it bluntly, his time as Suffolk County Sheriff up until this point has not been without scandal. The previous times when he's gotten in trouble, it's been at the State Ethics Commission level, and he's been dinged for fines a couple times for hiring his niece. That was one thing. There was another instance where he basically demanded that store owners in the district take down political signs of his political opponent. And he invoked his position as sheriff while doing that. So he got fined for that. In 2013, Tompkins was campaigning for re-election as the incumbent sheriff. According to reporting in the Boston Globe, Tompkins walked into several shops in Boston, identified himself as the sheriff and demanded that they remove his opponent's campaign posters.

13:24Forcing people to take campaign signs of your opponent down, it's relatively small potatoes, but it does give you a glimpse into some of the thinking. Because, like, his opponent at that time, there was no way that his opponent was going to win, like Steve was going to crush him. But he still pushed for these signs to be taken down. To me, the campaign sign incident did suggest that even though he must have known that he was going to cruise to re-election, he was still looking for an edge wherever he could find it, basically. For this pointless show of power, Tompkins was fined$2 ,500 in 2015.

14:06And he didn't learn his lesson. Tompkins was re-elected and continued to abuse his status as sheriff whenever he could. He found himself under scrutiny again in 2023 when he was accused of nepotism and misusing taxpayer money. A county sheriff is accused of abusing his office by asking employees to run personal errands and creating an entirely new position for a family member. And as Christina Rex explains, it was all at taxpayer expense. The allegations start back in 2014 when Suffolk County Sheriff Stephen Tompkins allegedly started taking favors from staff, then later hired his own niece to the department but used her for child care.

14:53Tompkins was found guilty of this offense and paid a$12 ,000 civil penalty in 2023. For a man who believes strongly in second chances, by 2025 he seemed to be on his third. Little did Tompkins know he would soon be in the position to ask for a fourth chance for redemption from his constituents, his peers, and now the United States federal government. But would he deserve it?

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16:35Sheriff Stephen Tompkins was a well-liked political figure in the Boston area. But he was also a magnet for trouble and found himself in hot water again and again due to a surprising lack of ethical judgment. Weird blind spot for a sheriff, right? Even so, he always managed to talk his way out of major consequences, and his career remained on track. This could have something to do with the allies he had within the Massachusetts political sphere. One of whom was his friend and former boss, Andrea Cabral. She was the former sheriff and a state government official for years until she left to work for Ascend Wellness, a Massachusetts-based cannabis company.

17:24This is Dan McDonald from the Boston Globe.

17:30Voters legalized cannabis in 2016. The cannabis regulators in the state, like the main board, is in a bit of disarray. The top commissioner of cannabis regulations was recently removed in Massachusetts. They were accused of bullying and verbally abusing employees. So it's a bit of a mess. I think most objective observers would say that the state has sort of fumbled on regulating cannabis. It's in total disarray, essentially. While Massachusetts' rollout of cannabis legalization may not have been smooth, it has become a majorly lucrative business. According to the Cannabis Control Commission of Massachusetts, Suffolk County alone made over$189 million in gross cannabis sales in 2024.

18:24With that kind of money on the table, you can imagine why Andrea Cabral left the public sector to work in corporate cannabis. And even though Cabral and Tompkins were no longer on the same payroll, They found a way to continue working together. In an interview with the Boston Globe in 2018, Cabral talks about collaborating with the Sheriff's Department with a job re-entry program. This program paired Ascend Wellness with the Suffolk County Sheriff's Department and aimed to connect people who were recently released from jail with jobs at Ascend Wellness facilities. The Sheriff's Department was enthusiastic about the job reentry program, which would fall under the department's Common Ground Institute.

19:11This was one of Tompkins' passion projects. Here he is talking it up in 2019. And then we have one other program called the Common Ground Institute, or CGI, where we place a very heavy emphasis on vocational education. As I mentioned, on average, our population has a fifth or sixth grade literacy and mathematics acumen. So the vast majority are not going to go to college, but they do need to know how to take care of themselves. And so when they come in, if they don't have their high school diploma, that's the first thing that we do. And then we follow that with the vocational education approach where we teach them carpentry, landscaping, custodial maintenance.

19:48We have a culinary arts program. We have an urban farm. and then we'd talk to employers and say, look, while Joe or Jane Public was here, they didn't just sit on their laurels, they actually did learn something. And so would you give them at least an interview? And we've had some pretty good success with guys and ladies getting interviews and getting jobs. Tompkins stated that he believed his partnership with Ascend would help break the cycle and repair some of the damage done to his constituents by the war on drugs. This program and his friendship with Cabral would solidify Tompkins' relationship with Ascend.

20:25And just a few short years later, it was this collaboration that would threaten Tompkins' political career, as he was caught with a metaphorical smoking gun in his hand. The Suffolk County Sheriff went before a federal grand jury today. He's facing extortion charges relating to a cannabis company. Even after Andrea Cabral left Ascend Wellness and was replaced by cannabis lobbyist Frank Perullo, Ascend maintained a close relationship with the Suffolk County Sheriff's Department. This was a necessary legal move. In Massachusetts, cannabis companies can only maintain annual licensure if they can prove they have a positive impact on their community.

21:13For Ascend, this was their jobs re-entry program collaboration with the Sheriff's Department. This put Sheriff Tompkins in a powerful position. He alone could decide if this business would continue to operate year after year. And in keeping with his previous ethical lapses, Tompkins took advantage of that. He is alleged to have extorted this company. Basically, he's kind of elbowed his way in to buy$50 ,000 worth of stock. And just to be clear, his office was instrumental in getting what's called a positive impact plan, which is a key part of the permitting process in this cannabis company getting the green light from regulators.

21:59So his office needs to sign off, essentially, on this positive impact plan. In 2020, Ascend started the permitting process to open a retail location in Boston. Because they had everything in order, including an approved positive impact plan that featured the jobs re-entry program, their license was approved. But according to court documents, Tompkins swooped in while the license was processing and demanded to buy stock in the company before it went public. The indictment states Tompkins, quote, wanted to get on the stock so he could make some cannabis money and take part in the IPO. Prosecutors said Tompkins pressured someone in the company to sell the stock to him before the company went public.

22:49The Suffolk County Sheriff's salary is$191 ,000 a year, so it's not like he was an underpaid public servant. Even still, Tompkins might have thought a little more cash in the bank wouldn't hurt. Court documents outline the rest of the extortion as a tense affair. Frank Perullo, the president of Ascend at the time, initially refused Sheriff Tompkins' request. But like a cartoon villain, Tompkins reminded him that Ascend's future licensure rested in his hands. Backed into a corner and fearful of tangling with the sheriff, Perulo sold Tompkins$50 ,000 worth of shares in November of 2020. And for a while, this seemed like a great deal to Tompkins.

23:40His$50 ,000 in shares became worth over$138 ,000 by 2021, and no one was the wiser to his bullying and extortion. But business is a fickle thing. By May 2022, Ascent's stock had tanked, and Tompkins' shares were now worth less than he initially paid for them. A normal person would just take the loss, but Tompkins wasn't satisfied with that. If he was going to bother to extort someone, he wanted it to be profitable. So he did something crazy. He asked for his money back. He allegedly elbowed his way into this cannabis company, bought$50 ,000 worth of stock, and then after it went public and the stock tanked, he's alleged to have demanded the$50 ,000 back.

24:35The darkly ironic thing is that he's in all this trouble and he didn't make a red cent, allegedly, from this scheme. Sheriff Tompkins demanded that Frank Perullo pay him his$50 ,000 back in full. And because Perullo still needed to maintain a positive relationship with the sheriff, he acquiesced. Tompkins' money was repaid to him over five installments, labeled as loan repayment or company expense. Because you can't write extortion on a memo line. With no money to make his crime worth his time, Tompkins moved on. He found another ethically dubious way to use his sheriff's badge for questionable perks.

25:27We found that his office has spent more than 60 grand during the last fiscal year on travel and food and, yeah, lodging and stuff like that. and that his office has paid for trips to Las Vegas and the Bahamas. And they spent$3 ,400 at Topgolf. And they had dropped six grand on this really bougie luxury hotel in Boston. And to be clear, there's no suggestion that any of it is illegal. But I think some people would ask, okay, what is the Suffolk County Sheriff doing in Las Vegas and the Bahamas and Baltimore? and we're just talking about one year. That's a lot of travel for a position that is Boston-based.

26:17The Boston Herald reports even higher numbers than$60 ,000 of unnecessary spending. According to some sources, Sheriff Tompkins used his government-issued procurement card for over$130 ,000 in purchases during 2025 alone. There are strict guidelines in place for how public officials use their procurement cards, or P-cards. For example, rules state that the cards can't be used for meals, snacks, or coffee. Which is interesting, because$1 ,900 was spent on Tompkins' P-card at the Margaritaville Beach Resort in the Bahamas, and labeled as eating places, comma, restaurants. And just to be clear, it's all public money, so ultimately the public is paying for this stuff.

27:09And of course it raises questions of like, well, is this what the public should be paying for? While Tompkins is not currently under investigation for his discretionary spending, it certainly raises eyebrows. It makes him look like the kind of person who can't be trusted and who will take advantage of every opportunity possible to abuse their power or privilege. It also makes him look like the kind of person that the feds in Boston would like to make an example out of. It's funny because like recently the attorney's office in Boston, they really care about public corruption a lot. There was a Boston city counselor who was recently indicted and ended up pleading guilty to corruption charges.

28:00I don't think it was more than$10 ,000. It was not a lot of money, but they still charged her federally. I think the thinking there is that, well, if this person will do it for peanuts, imagine what they would do if someone comes along with some real money. The feds in Boston love public corruption cases. They love to make an example of elected officials, even if the money isn't that much. Over the years, it's definitely been a priority of theirs, for sure. With the U.S. attorney's office hungry to root out corruption in Boston, a history of misconduct, and a paper trail of extortion leading back to Tompkins, could the sheriff avoid the line of fire?

28:56Sheriff Stephen Tompkins acts less like a man of law and more like a man of opportunity. Whether it means bullying a shop owner to take down his opponent's campaign posters, creating a babysitting job for his niece on the sheriff's department's payroll, swiping his government-issued procurement card to pay for extravagant vacations, or criminally extorting a business for pre-IPO stock, Tompkins never fails to milk his sheriff's badge for all it's worth. That's what he was doing when he was taken into custody by FBI agents on August 8, 2025, in Fort Lauderdale, Florida. The Suffolk County Sheriff now facing federal charges.