Sheriff Tompkins accused of committing extortion by leveraging licensing ties to demand $50K in stock from a cannabis company preparing for its IPO
When federal prosecutors unsealed an indictment on Aug. 8, 2025, against Suffolk County Sheriff Steven W. Tompkins, they painted a picture of a public official blurring the line between civic duty and personal profit.
The charges—two counts of extortion under color of official right—center on an alleged scheme that began in 2020 and wound its way through Boston’s cannabis industry, touching both the sheriff’s re-entry employment program and the state’s cannabis licensing process.
Tompkins, 63, has run the Suffolk County Sheriff’s Department since 2013, overseeing about 1,000 staff and shaping the department’s public-facing partnerships. Those partnerships have included a 2019 “Positive Impact Plan” with a Boston-based cannabis company—an initiative intended to help formerly incarcerated people find jobs.
That plan was not just good optics; it played a documented role in the company’s application with the Massachusetts Cannabis Control Commission.
Prosecutors now allege Tompkins used that goodwill—and his position—to pressure an executive at the same company into a $50,000 pre-IPO stock sale from the executive’s personal retirement account.
From Re-Entry Ally to Accused Extortionist
In 2019, the Boston cannabis company sought to bolster its state license application by demonstrating ties to community re-entry work. Partnering with Tompkins’ department checked that box. Massachusetts’ cannabis licensing process rewards companies that can show such social equity contributions, and in Boston’s competitive market, every point matters.
By early 2020, according to federal court filings, Tompkins approached a company executive with a proposition: sell him roughly 14,417 shares at $1.73 each, for a total of about $50,000. The indictment alleges the request wasn’t framed as friendly investment advice. Instead, prosecutors say, the sheriff leveraged his role in the licensing-linked partnership to secure the deal, creating what they characterize as a coercive environment.
The company agreed to the sale. The IPO followed in 2021, sending shares to a high of $9.60 each—at least briefly making Tompkins’ paper gains look like the stuff of day-trader dreams.
Stock Rise, Stock Fall, and a Sudden “Loan Repayment”
Like many cannabis stocks in the post-IPO era, the glow didn’t last. By 2022, the stock’s value had deflated. Federal prosecutors say that’s when Tompkins demanded the executive return his full $50,000, despite no evidence the shares were sold back or that any contractual obligation existed.
The repayment, prosecutors allege, came via checks labeled “loan repayment,” a detail suggesting an attempt to cloak the true nature of the transaction.
By that point, any line between Tompkins’ public office and private financial dealings was not just blurred—it was under federal microscope.
Arrest, Charges, and Potential Penalties
On Aug. 8, Tompkins was arrested in Florida while attending an event. The indictment charges him with two counts of extortion under color of official right—a statute often used to prosecute public officials who misuse their authority for personal gain.
If convicted, he faces up to 20 years in federal prison, a $250,000 fine, and up to three years of supervised release. Those are maximums; sentencing guidelines would likely produce a shorter term, but the political fallout could be immediate and permanent.
U.S. Attorney Leah Foley emphasized the breach of public trust, noting that when public officials personally benefit from relationships tied to their official duties, “the entire system’s legitimacy is at risk.”
The Players and the Stakes
The indictment leaves some gaps. The cannabis company is not named. Neither are its executives. Public records may eventually connect the dots, but for now, federal prosecutors are keeping those details sealed.
The stakeholders are easy enough to map:
- Sheriff Tompkins — Longtime political figure, with community program leverage and a reputation as a re-entry advocate. Now facing allegations that his advocacy doubled as leverage for personal enrichment.
- Cannabis company executive — A decision-maker with licensing at stake, potentially reluctant to refuse an official who could influence public perception of the company’s social equity credentials.
- U.S. Attorney’s Office — Positioning this as a clear-cut case of corruption, both to deter similar conduct and to underscore that Massachusetts’ cannabis industry is under watch.
- Public and program beneficiaries — Those served by re-entry programs may now wonder whether partnerships are rooted in genuine commitment or transactional benefits for those in power.
Legal and Ethical Gray Zones
Tompkins’ defense could argue that the stock purchase was voluntary—an arm’s-length transaction between acquaintances. If the executive saw the sheriff as a personal friend rather than a licensing gatekeeper, the optics might shift.
Yet the “under color of official right” statute doesn’t require explicit threats or direct quid pro quo. It’s enough if prosecutors can show the official’s position created implicit pressure. In industries like cannabis—where licensing is a high-stakes, politically sensitive process—the power imbalance can be implicit but potent.
That raises larger questions: Should public officials ever be in business, even tangentially, with entities connected to their official work? Can a good-faith community program ever fully insulate itself from suspicion when money changes hands?
What’s Next in Court
The indictment is just the opening salvo. Over the coming months, expect:
- Defense motions challenging the scope and interpretation of “official right” in this case.
- Possible plea negotiations, especially if prosecutors have documentary evidence of pressure or repayment arrangements.
- Discovery requests revealing whether the cannabis company sought legal advice before selling the stock.
- Community reactions, particularly from re-entry program advocates who may feel betrayed.
If the case proceeds to trial, testimony from the unnamed executive could be pivotal. That witness’s credibility—and any evidence of discomfort or perceived pressure—will likely be the prosecution’s linchpin.
A Broader Warning for Cannabis Partnerships
Massachusetts’ legalization framework encourages cannabis companies to embed themselves in local communities through hiring programs, charitable work, and partnerships with nonprofits or government agencies. These arrangements can create meaningful opportunities for people with prior convictions.
They can also, as this case suggests, create a proximity to power that makes corruption easier to allege and harder to disprove. Even the perception of impropriety can be damaging, eroding public trust in both the industry and the officials involved.
For cannabis entrepreneurs and public agencies alike, the lesson is simple: keep financial transactions transparent, arm’s length, and documented with contracts that can survive scrutiny.
A Message to Other States
While this indictment is Massachusetts-centric, the implications ripple far beyond Boston. States with newly legalized cannabis markets—Arizona among them—should note how easily community benefit programs can become entangled in ethics probes. For public officials, the safest investment is in the credibility of the programs they oversee, not in the companies that benefit from them.
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