Suffolk Sheriff Steven Tompkins goes on trial today — and the outcome could reshape Boston's political landscape.

Jury selection begins this morning in federal court for Sheriff Steven W. Tompkins, the 69-year-old Suffolk County sheriff who's spent years as one of Greater Boston's most recognizable political figures. Federal prosecutors allege Tompkins used his office to extort a cannabis company — Ascend Mass — not once but twice: first pressuring the company for early access to buy $50,000 in stock, then leaning on them again to get his money back after the stock cratered. His attorney, Martin Weinberg, says it's nothing more than a business deal between old friends that had nothing to do with Tompkins's badge.

Here's why this matters beyond the courtroom drama: Tompkins has held the sheriff's post since 2013, overseeing the Nashua Street Jail and South Bay House of Correction, and he's been a fixture at every ribbon-cutting and campaign event in the city for over a decade. A conviction wouldn't just end a career — it would trigger a scramble for one of the more powerful, patronage-rich offices in Massachusetts government, one that's largely escaped public scrutiny for years. The case also lands at an awkward moment for Democrats statewide, as Governor Maura Healey works overtime to burnish her own public-safety credentials against two Republican challengers ahead of November. A corruption trial involving a sitting Democratic sheriff is not the backdrop anyone in the party wanted heading into election season.

Watch for how prosecutors handle the "quid pro quo" question — Weinberg's defense hinges entirely on convincing jurors this was a legitimate financial transaction, not official corruption. That's a high bar for prosecutors, but juries in extortion-under-color-of-official-right cases can be unpredictable. Expect this trial to run for weeks and dominate Boston political conversation through the fall.

Full story at Boston Globe →

Healey leans into public safety as GOP rivals circle. With two Republicans challenging her reelection bid, Governor Healey has spent recent months pushing a former prosecutor onto the Parole Board and touting crime-decrease ad campaigns from allied nonprofits — all while insisting none of it is about the campaign. Her record as a career prosecutor is becoming her shield against attacks that Massachusetts is soft on crime. Boston Globe →

Early voting is underway — but it might not matter much anymore. Massachusetts kicked off its early voting window for the state primary this weekend, running through Friday, August 28. Secretary of State Bill Galvin says turnout at physical polling sites has cooled as more voters shift to mail-in ballots, which they can fill out from home on their own schedule. Find your options at VoteInMA.com. WBZ / CBS Boston →

Federal election monitors are heading to New Bedford — and some officials aren't thrilled. Boston has hosted Department of Justice election monitors for decades without much fuss, but New Bedford's addition to the list this cycle is raising eyebrows among state officials. The move comes amid broader national tension over federal involvement in local elections. MassLive →

Quincy's religious statue plan hits a wall at the state's highest court. The Supreme Judicial Court unanimously sided against Mayor Thomas Koch's push to install 10-foot bronze statues of St. Michael and St. Florian outside the city's public safety building, finding the imagery too overtly religious to pass constitutional muster. The ACLU sued on behalf of 15 Quincy residents last year, and the case now heads back to a lower court where those residents are considered likely to prevail. Boston.com →

Marshfield's Select Board just reshaped how the town funds its schools. In a contentious 2-1 vote, the board approved a new revenue-sharing agreement guaranteeing Marshfield Public Schools 68.5% of shared town revenue, tied to a "no new override" pledge, alongside new efficiency audits. The board also opened the warrant for an October 19 special town meeting and welcomed new Town Administrator Ted Langill on his first day — a lot of change for one Monday night meeting. South Shore News →

Norwell rewards its superintendent for steering through a brutal budget year. The Norwell School Committee unanimously gave Superintendent Matthew Keegan a 3.5% merit raise after a year defined by staff cuts and belt-tightening following a failed override vote. Committee members praised his multi-year financial planning as the district also awaits word on a Massachusetts School Building Authority feasibility study for a new Norwell High School. South Shore News →

Tonight, 7-8 p.m.: WATD hosts a live candidate forum for the 9th Congressional District Democratic primary, featuring incumbent Congressman Bill Keating and challenger Craig Swallow. Submit questions by noon today. WATD →

Through Friday, August 28: Early voting continues statewide for the September primary — check hours and locations for your city or town before they close out the week. WBZ / CBS Boston →

This week in federal court, Boston: Jury selection and opening arguments are expected in the Sheriff Tompkins extortion trial — one to watch if you follow Suffolk County politics. Boston Globe →

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Recent filings with the Massachusetts Office of Campaign and Political Finance:

Candidates

• Gabriel Greenspan (Republican) — Senate, Berkshire, Hampden, Franklin and Hampshire — Filed: 8/20/2026
• Anthony Baez — City Councilor, Boston — Filed: 8/20/2026
• Brendalee Smith (Republican) — House, 10th Bristol — Filed: 8/19/2026

Ballot Question Committees

• Vote YES on 4 Election Day Registration — N/A, No office — Filed: 8/19/2026

Change of Purposes

• Christopher Chan — City Councilor, Quincy → Mayoral, Quincy — Filed: 8/21/2026

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