WBUR reports
The star prosecution witness in the federal corruption trial of Suffolk County Sheriff Steven Tompkins read aloud private texts and emails the two exchanged over the years, writing at one point about his “love” for the man he’s now testifying against.
Prosecutors asked the witness, Frank Perullo, a cannabis executive, to read aloud several of the exchanges, highlighting what they said was the close friendship he shared with Tompkins.
Prosecutors allege that Tompkins, as sheriff, pressured Perullo to sell him $50,000 of stock before Perullo’s company, Ascend Wellness Holdings, went public. And when the stock value plummeted, Tompkins allegedly demanded the full amount of the investment back, rather than eat the loss.
Perullo accepted immunity from prosecution in exchange for providing testimony testifying against the sheriff. Tompkins, who’s facing extortion charges and is on leave from his elected position, has maintained his innocence.
“I need Tompkins Time,” Perullo wrote to the sheriff at one point. “I miss you.” They exchanged “I love you” notes, with Tompkins calling Perullo “my brother.” In September of 2021, prosecutors questioned Perullo about why he emailed a group of voters to boost Tompkins’ re-election bid, calling his friend “a man of integrity.”
Despite the closeness exhibited by the messages, Perullo told prosecutors he didn’t want to give Tomkins an investment stake in the company — and he really didn’t want to refund Tompkins once the stock fell in value.
Tompkins didn’t sign any agreement that would have guaranteed a refund, according to the indictment. Still, Perullo did repay him, mostly in $12,000 or $12,500 increments. Some of the checks, Perullo said under questioning by the government, included memos to ensure the money went untaxed — at Tomkins’ urging.
He was very “persistent” about repayment, Perullo said. In another message Tompkins allegedly sent from Las Vegas, the sheriff wrote to Perullo “Time to hit the ballroom and bet on the ponies.”
Perullo said he felt pressure tosell the stock and then reimburse Tompkins because Ascend had a deal with the sheriff’s office to hire people released from jail as part of a community impact requirement for a state cannabis license.
Defense attorneys took a different view of the messages, saying it contradicted the prosecutors position that Perullo was unwilling to sell the stock to Tompkins.
Their questions hammered the same points: Why would Perullo, who claims he was being extorted, say “I love you” between payments to Tompkins? Why wouldn’t he just tell his friend “no?”
Attorney Martin Weinberg asked Perullo if he struggled to say no, which Perullo said he didn’t. “You’re not easily intimidated.”
“Not usually, no,” Perullo responded.
Weinberg noted other efforts Ascend was making to meet “positive impact” requirement of its license beyond the job training program. Ascend donated around $1 million to the Last Prisoner Project, which works to free incarcerated people imprisoned for crimes related to the sale, transport and use of cannabis.
Perullo confirmed that he’d never gotten word that the license was in trouble — neither formally from the Cannabis Control Commission nor informally from Andrea Cabral, the former Suffolk County Sheriff, who was a former executive at Ascend and a close friend of Tompkins. She’s expected to testify this week.
Weinberg also asked about the immunity deal Perullo made with prosecutors, noting that he would face major financial “peril” if he were charged with a crime in relation to his dealings with Tompkins. The defense pointed to his recent purchase of a $4.7 million home in Lexington.
Tompkins, if convicted, faces two extortion charges, each of which carries a maximum sentence of 20 years in prison, though, if convicted, it’s unclear how much time he would actually face under federal sentencing guidelines.
This segment aired on August 31, 2026. The audio for this segment is not available.
