For a guy who holds a fairly obscure elected county office, one that voters have little to no contact with – if they are lucky – Steve Tompkins managed to make himself a remarkably visible player on the political scene. He threw in early with Elizabeth Warren in 2012 as she ran for US Senate and spoke eight years later at her presidential campaign kickoff in 2020. He’s been a prominent ally of Boston Mayor Michelle Wu’s, and once made a run at chairing the Massachusetts Democratic Party.  

While Tompkins has adeptly leveraged his office to forge a deep well of political connections, his resume for the job itself was remarkably thin when Gov. Deval Patrick named him Suffolk County sheriff in 2013 after tapping then-Sheriff Andrea Cabral to serve as his public safety secretary. Tompkins had served as communications chief to Cabral, a college classmate from Boston College, but had no formal background in corrections or law enforcement.  

When Patrick was questioned at the time about the appointment, he said the quiet part out loud about Massachusetts sheriffs, who have responsibility for managing complex county correctional facilities but get the job by political fundraising, campaigning, and winning elections to six-year terms. “It’s a political job, so the folks that are criticizing it as a political hire, tell them: They’re right,” Patrick said after swearing in Tompkins.  

While he may earn points for candor, Patrick’s “political hire” to fill the sheriff’s seat until the next election does not, in hindsight, look like one of his finer personnel picks in the wake of Tompkins’s indictment last month on federal corruption charges.  

Tompkins, who has handily won three election campaigns since his appointment, is charged with extortion involving a cannabis company whose stock he’s alleged to have pressured the firm to sell to him before the business went public. The indictment alleges that he later demanded to be repaid his initial investment, despite the value of the stock falling below his purchase price. The company had a partnership with the sheriff’s office to train released inmates for jobs in the cannabis industry, something key to its licensing under the state law requiring cannabis firms to invest in communities and individuals disproportionately affected by past sanctions against marijuana.  

Tompkins entered a not guilty plea to the charges. He has not commented, but his lawyer, Martin Weinberg, said following Tompkins’s arraignment, “The facts simply will demonstrate that he was charged with a crime he did not commit.”  

Tompkins’s use of the sheriff’s perch as a springboard to affable – and ambitious – player in Democratic politics highlights what Boston College political science professor David Hopkins calls the “odd and vestigial” practice of electing people who are essentially regional correctional commissioners, with voters often having little basis to evaluate whether they’re doing a good job or not.

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Published by MassINC