Suffolk County Sheriff Steven W. Tompkins, a towering figure in Boston’s political landscape, now finds himself at the heart of a federal criminal case that has sent shockwaves through Massachusetts politics. On August 8, 2025, Tompkins, age 67, was arrested in the Southern District of Florida and charged with two counts of federal extortion. The charges stem from his alleged use of public office to pressure a Boston cannabis company into granting him a lucrative stake—then demanding repayment when the investment soured.
According to federal prosecutors, Tompkins approached an executive at Ascend Mass, a cannabis company operating in Boston, for early access to company stock before it went public. The company had partnered with the Suffolk County Sheriff’s Department in 2019, a collaboration that helped fulfill state licensing requirements promoting positive impact on communities affected by past marijuana laws. This partnership, crucial for Ascend’s license applications and renewals from 2020 through 2023, gave Tompkins a unique position of influence.
Court documents allege that Tompkins suggested Ascend’s partnership with his department could be at risk if he did not receive shares. In late 2020, Tompkins purchased $50,000 worth of pre-IPO stock in Ascend. When the company went public in 2021, the shares shot up in value to over $138,000. But as the market cooled and the stock price dropped below his purchase price, Tompkins allegedly demanded the return of his initial investment.
Between May 2022 and July 2023, the executive at Ascend repaid Tompkins in five checks, each for $10,000. Prosecutors claim some of these checks were labeled in ways meant to disguise their true purpose. The indictment asserts that Tompkins demanded the money for “his campaign and personal expenses,” despite having no agreement guaranteeing a refund on his investment. If convicted, Tompkins faces up to 20 years in federal prison for each count, along with possible fines and supervised release.
Tompkins’s arrest and the details of the indictment have reignited discussion about the intersection of politics, power, and accountability in Massachusetts. The sheriff’s office has not issued a statement since the charges were filed, and Tompkins himself has not responded to requests for comment regarding his future as sheriff. He was released on $200,000 bail after his initial appearance in Florida and is required to report to federal court in Boston by August 15, with arraignment scheduled for a later date.
The legal and political ramifications of the case are significant, not least because of the unusual protections Massachusetts law affords to elected sheriffs. As reported by The Boston Globe, a 1994 Massachusetts Supreme Judicial Court (SJC) decision established that neither the governor nor the attorney general has the power to suspend an elected sheriff. Only the SJC itself—or the voters—can remove or place a sheriff on leave. This precedent means that, unless Tompkins chooses to resign, he can remain in office unless the court or the electorate acts. If he is convicted and sentenced to prison, however, state law deems the office vacant, allowing the governor to appoint an interim replacement and call a special election.
This legal wrinkle echoes the saga of former Middlesex Sheriff John P. McGonigle, who was indicted and ultimately suspended by the SJC before a federal conviction ended his tenure. The current situation has left Massachusetts officials in a holding pattern. Governor Maura Healey and Attorney General Andrea Campbell have not commented on whether they will petition the SJC for Tompkins’s removal. The Massachusetts Sheriffs’ Association, for its part, stated, “Given the active nature of this investigation, the Massachusetts Sheriffs’ Association will respect the parties in this case, and allow the legal process to play out.”
Local politicians have largely refrained from calling for Tompkins’s resignation. Boston Mayor Michelle Wu, an ally of Tompkins, described the charges as “very serious” but said she would reserve judgment until more facts emerged. City Councilors Ed Flynn and Erin Murphy echoed Wu’s sentiment, with Flynn emphasizing, “Ethical and positive leadership, honesty and integrity must be demonstrated by elected officials and public servants.” The contrast with the recent resignation of Boston City Councilor Tania Fernandes Anderson—who stepped down after pleading guilty to bribery charges—has not gone unnoticed by observers.
Tompkins’s career has been defined by both public service and controversy. He joined the Suffolk County Sheriff’s Department in 2002, initially serving as Chief of External Affairs, where he built partnerships with community groups and launched programs like the Common Ground Institute for vocational training and the Choice Program for youth outreach. In 2013, Governor Deval Patrick appointed him sheriff, succeeding Andrea Cabral. Tompkins was subsequently elected in 2014 and re-elected in 2016 and 2022, managing nearly 1,000 staff and overseeing the Suffolk County House of Correction, Jail, and Civil Process Division.
His resume is extensive: chairman of the board at Roxbury Community College, past president of the Massachusetts Sheriff’s Association, and a leader in the National Organization of Law Enforcement Executives. Tompkins holds a bachelor’s degree from Boston College and a master’s from the University of Massachusetts, with prior stints in community health, cable television, and FEMA communications.
Yet, Tompkins’s tenure has not been without ethical lapses. In 2015, he paid a $2,500 fine and admitted wrongdoing after using his position to pressure store owners to remove campaign signs for his election opponent. He told The Boston Globe at the time, “It won’t happen again.” But it did. In 2023, he paid a $12,300 fine for creating a no-bid job for his niece and asking subordinates to run personal errands. Altogether, Tompkins has paid $14,800 in ethics fines over the years, according to The Boston Herald.
Tompkins’s political connections run deep, but recent reports suggest his campaign finances are strained, with just $4,400.27 in cash on hand. His arrest has drawn comparisons to a long line of Massachusetts sheriffs who have faced legal trouble, including John McGonigle and Charles Reardon. The case has also sparked speculation about potential successors, with names like City Councilor Ed Flynn and State Senator Lydia Edwards floating in Boston’s political circles.
For now, the fate of Suffolk County’s High Sheriff hangs in the balance. As the legal process unfolds, the case stands as a stark reminder of the power—and pitfalls—of public office in Massachusetts. The community, the courts, and the political establishment are all watching closely, waiting to see what comes next for Steven W. Tompkins and the office he has long commanded.
