The trial of Suffolk County Sheriff Steven Tompkins, who is accused of two counts of extortion in relation to dealings he had with political operative turned marijuana entrepreneur Frank Perullo, begins on Aug. 24 and is expected to last two weeks, according to court filings.
Tompkins is a well-known figure in Massachusetts political circles. Previously a spokesperson for then-Suffolk County Sheriff Andrea Cabral, he was tapped by then-Gov. Deval Patrick to become sheriff himself when Cabral joined Patrick’s cabinet in 2013. Tompkins has also previously run to be head of the Massachusetts Democratic Party, worked as a senior advisor for Elizabeth Warren’s first Senate campaign, and endorsed then-Boston City Councilor Michelle Wu’s bid for mayor in 2021.
Federal prosecutors contend that Tompkins extorted Perullo by obtaining a $50,000 pre-IPO investment in Perullo’s company, Ascend Wellness Holdings. Prosecutors allege that Tompkins suggested that the Suffolk County Sheriff’s Department (SCSD) would not maintain a vital community partnership with Ascend unless Tompkins was allowed to make his investment.
Prosecutors also say Tompkins then got a full refund of that investment when the value of the stock dropped, as Perullo purportedly feared that same outcome if Tompkins’ initial investment was not returned.
The partnership in question involved the SCSD helping formerly incarcerated persons re-entering the community to get jobs at Ascend’s retail stores. The state’s Cannabis Control Commission requires that companies operating in Massachusetts show they’re working to mitigate harm in areas that were disproportionately impacted by the criminalization of cannabis.
In its court filings, the defense indicates it will argue that the government can’t show that a quid pro quo bribery agreement existed between Tompkins and Perullo. Instead, the defense will argue, the business transactions involving Ascend stock were just that: above-board interactions between two friends rather than illicit concessions made in return for beneficial official actions.
The defense also plans to argue that Perullo never had any reasonable fear of economic harm, and that Tompkins never believed he was doing anything wrong as he sought to purchase Ascend stock and then recoup his initial investment.
Prosecutors say they plan to call Perullo and other current and former Ascend employees and former SCSD employees, among others to the stand. Their roster of witnesses also includes an employee of Massachusetts’ State Ethics Commission, who will speak about Tompkins’ previous acknowledgments that he violated state ethics laws by using his office for personal gain.
The defense’s plans for witnesses are less clear from court filings, and Tompkins’ attorney Martin Weinberg was not available for comment Friday.
Weinberg’s past clients include Karen Read. Jeffrey Epstein and parents in the so-called “Operation Varsity Blues” cases.
Following Tompkins’ arrest in Florida in 2025, Leah Foley, the U.S. Attorney for Massachusetts, called his alleged behavior an “affront to the voters and taxpayers who elected him.”
“Elected officials, particularly those in law enforcement, are expected to be ethical, honest and law abiding — not self-serving,” Foley said.
Tompkins did not immediately respond to a request for comment from GBH News.
