Crime and politics
Tompkins was arrested Friday in Florida and is accused of extorting $50,000 from a cannabis company that was looking to set up shop in Boston. According to the indictment, Tompkins allegedly used his position as sheriff to pressure an executive to sell him stock in the unnamed company before it went public. Later, when the investment didn't pan out, Tompkins demanded that the company pay his investment back as he faced a reelection campaign, the indictment alleges.
There are a lot of hypotheticals to wade through, but there's already talk about who could replace Tompkins if he's ultimately ousted or resigns. Boston City Councilor Ed Flynn has been floated as a potential candidate since before the indictment amid speculation that Tompkins wouldn't run for another term (he currently has only about $4,000 in his campaign account). Former state Rep. Evandro Carvalho is also being floated as a possible successor, and a recent Boston Herald column over the weekend added Democratic state Sen. Lydia Edwards's name into the mix.
A job that the Boston Globe's Adrian Walker recently described as 'one step removed from witness protection' isn't exactly where you'd expect any ambitious politicians to end up. But Tompkins has used the position to hold significant sway in Boston politics, and sheriffs across the state have been in the headlines lately amid debate over whether and how local law enforcement should work with Immigration and Customs Enforcement authorities.
For now, the claim that Tompkins extorted a Boston-based cannabis company isn't prompting calls from top Democrats for him to step down. The allegations against Tompkins haven't been proven, but the innocent-until-proven-guilty factor hasn't stopped top politicians from weighing in on other recent scandals.
Healey quickly called on Democratic state Rep. Chris Flanagan to resign after he was arrested in April for allegedly stealing tens of thousands of dollars from his former employer. And Boston Mayor Michelle Wu and many members of the City Council called on former City Councilor Tania Fernandes Anderson to step down after she was indicted for her involvement in a kickback scheme late last year. Fernandes Anderson later pleaded guilty to federal charges of wire fraud and theft.
It's not Tompkins's first brush with the law. He forked over $2,500 in fines in 2015 after leveraging his position as sheriff to attempt to get a store owner to take down campaign signs that belonged to a political opponent. And in 2023, he paid a $12,300 civil fine for violating the state's conflict of interest law.
Healey can't remove Tompkins, but she and Attorney General Andrea Campbell could petition the Supreme Judicial Court to do so, as the Boston Globe laid out over the weekend. Healey has appointed two of the seven justices currently sitting on the state's highest court.
So what happens if Tompkins is removed? There are a couple of relevant recent case studies. Tompkins himself was appointed by Gov. Deval Patrick in 2013, after Patrick named then-Suffolk County Sheriff Andrea Cabral to be state secretary for public safety.
More recently, Healey tapped Lori Streeter to replace former Franklin County Sheriff Christopher Donelan in January, after Donelan's retirement. Though sheriffs aren't set to be on the ballot until 2028, Franklin County residents will get to weigh in on a permanent replacement for Donelan in 2026.
GOOD MONDAY MORNING, MASSACHUSETTS. Healey's Republican opponents are looking to capitalize on the news. Republicans Mike Kennealy and Brian Shortsleeve are both calling for Tompkins to be removed from his position on the Roxbury Community College Board of Trustees, the Boston Herald's Matthew Medsgar reports.
TODAY — Gov. Maura Healey and Lt. Gov. Kim Driscoll attend a ceremony for the reopening of Natick Center MBTA Station at 3 p.m. in Natick. Rep. Seth Moulton visits veterans at the Ironstone Farm at noon in Andover and joins volunteers at Beverly Bootstrap at 2 p.m. in Beverly. Rep. Jim McGovern hosts a public conversation with former director of the Consumer Financial Protection Bureau Rohit Chopra at 6 p.m. in Greenfield.
Have a tip, story, suggestion, birthday, anniversary, new job, or any other nugget for the Playbook? Drop me a line: kgarrity@politico.com.
DATELINE BEACON HILL
— Mass. Gov. Healey signs $1.2B bill for roads and bridges by John L. Micek, MassLive: 'Cities and towns across Massachusetts will see more state money for road, bridge and public infrastructure projects under a sprawling, $1.2 billion transportation funding bill that Gov. Maura Healey signed into law on Friday. Part of that money, $300 million, is earmarked for the state's Chapter 90 program, which provides local support for transportation projects. That includes, for instance, $6.3 million in funding for Springfield and $2.4 million for Chicopee in Western Massachusetts.'
THE MONEY
— State tax collections rose 7.1% last fiscal year by Chris Lisinski, State House News Service: 'Amid months of hand-wringing about the state's financial footing, Massachusetts ended the most recent budget cycle with tax collections that just about matched the official forecast for modest growth. Tax collections from all sources totaled $43.708 billion in fiscal 2025, a 7.1% increase over fiscal year 2024 and 5.1% more than the benchmark, the Department of Revenue announced Friday. That was driven by growth in the income surtax, capital gains tax revenues, sales and use taxes, and 'all other' taxes, which were 'partially offset' by decreases in corporate and business taxes, according to DOR Commissioner Geoffrey Snyder.'
TARIFF TALK — Sen. Elizabeth Warren acknowledged over the weekend that tariffs 'are an important tool in the toolbox for helping develop manufacturing here at home.' But the way President Donald Trump is deploying them is creating 'more chaos in the economy,' she said during an interview on WBZ's 'Keller @ Large' over the weekend.
And uncertainty over tariffs means people are playing the 'wait-and-see game' when it comes to hiring, Greater Boston Chamber of Commerce CEO Jim Rooney said during an interview on WCVB's 'On the Record' that aired Sunday.
'The warning signs are really about that paralysis,' Rooney said. Toy company Hasbro had been making plans to move its headquarters to Boston, Rooney pointed out, 'and they openly said that given the uncertainty about the tariffs, we're not going to make the move at that point.'
MORE — Tariffs hit Mass. construction firms by Grant Welker, Boston Business Journal: 'Tariffs are beginning to take a bite into Boston-area construction project budgets, and local contractors say the uncertainty around pricing may be the worst part of all. 'The uncertainty is driving us all crazy. It's impossible to make decisions,' said John McLaughlin, the president of the Dorchester-based electrical firm Sullivan & McLaughlin. But in an industry where the impulse may be to move a project forward, there is still a way to share risks, he added.'
FROM THE HUB
— After Boston's lab building boom, one-third of it sits empty. What do we do now? by Catherine Carlock, The Boston Globe: 'After a COVID-era building boom, the amount of lab space in Greater Boston has roughly doubled in the last five years, to 48.4 million square feet. Yet, in a striking instance of mistiming, the once-meteoric growth of the biomedical industry here has essentially stagnated, to the point where nearly 36 percent of that lab space is empty, according to brokerage firm Newmark. That's the highest vacancy rate on record.'
— Boston suicide prevention hearing order triggers City Council debate on terminology by Lance Reynolds, Boston Herald: 'A Boston city councilor wants to address measures to prevent suicides at high-rise garages after a person recently jumped to their death in Chinatown, causing a debate with a colleague who said she felt triggered by his language. The council referred Councilor Ed Flynn's order to the Committee on Public Health, Homelessness, and Recovery to set a hearing on the issue, while some members are urging their colleagues to be mindful of how their words may be taken.'
— South Boston bicyclist says he suffered hit-and-run after being clipped by car while in bike lane by Emily Spatz, The Boston Globe: 'A South Boston man was seriously injured after a collision that occurred while riding in a bike lane last week, which he says was caused by a passing car. Austin Barron said in an interview he was biking around Moakley Park at about 10 a.m. on Aug. 2, when a car sideswiped him before driving away. Barron, who was training for an Ironman competition, said he was in the bike lane on William J. Day Boulevard when he suddenly felt the force of a vehicle.'
THE RACE FOR CITY HALL
— Beauregard makes pitch for reelection by Teddy Tauscher, The Eagle-Tribune: 'While it has only been about a year since Mayor D.J. Beauregard, 36, entered office, and nine months since he was formally elected, he has faced an array of challenges including school cleanliness issues, a difficult budget season in part due to unpredictable state aid and lately litigation between the city and school. … The youngest mayor in the city's history is running for reelection this fall and promises to continue to be an 'agent of change' while also following in the footsteps of the late Mayor Neil Perry, whom he counts as a mentor. He is being challenged this fall by former cosmetics executive Barbara Stoebel.'
FROM THE DELEGATION
— Don't let the sun go down on Mass.: Markey slams Trump over solar program by John L. Micek, MassLive: 'You can count U.S. Sen. Ed Markey, D-Mass., among the chorus of Bay State pols who are less than thrilled over the Trump administration's decision to cancel a $7 billion grant program for solar energy. The Malden lawmaker, who sits on the Senate's Environment and Public Works Committee, slammed the Republican White House over what he called its 'unlawful' decision to stick a fork in the Solar for All Program. Sixty states, including Massachusetts, which was in line for $156 million, were impacted.'
MARIJUANA IN MASSACHUSETTS
— Cannabis impact fees: Where are they now? by Erin-Leigh Hoffman, Greenfield Recorder: 'As Aug. 11 marks the third anniversary of the adoption of the newest state rules regulating community impact fees on cannabis businesses, municipalities across Franklin County are left wondering what they can reasonably do with the thousands that have been collected amid a hazy future for the funding.'
FROM THE 413
— Rural towns see boost in road funding by Emilee Klein, Daily Hampshire Gazette: 'Rural towns in Hampshire County can go the distance on road repair after the state tweaked its Chapter 90 funding formula to give more weight to the number of miles of roads within a community. The Chapter 90 program distributes state aid to local municipalities for upkeep to public roads and bridges. Traditionally, the formula used to calculate the amount of aid per municipality weighs population, employment and road miles. The chosen variables often leave rural towns with more roads to maintain but fewer people with a lot less funds.'
THE LOCAL ANGLE
— After Third Bomb Threat In Five Days, More Questions Than Answers by Jason Graziadei, The Nantucket Current: 'The third bomb threat in five days struck Nantucket's Main Street Saturday night, once again prompting a significant police response that resulted in blocked streets, evacuated sidewalks, and shuttered businesses. Shortly after the island's largest summer event - the Boston Pops concert at Jetties Beach - concluded Saturday evening, Nantucket Police received a call from an individual claiming they intended to place an 'improvised explosive device' at the Ralph Lauren store at 16 Main Street. That location was also the target of the bomb threat last Tuesday and the subsequent bomb threat last Friday.'
— Cape Cod experiencing significant drought conditions by Zane Razzaq, Cape Cod Times: 'State officials are urging Cape Cod residents to minimize water use because the region is experiencing a significant drought. The Cape Cod region was upgraded to a Level 2 ― Significant Drought status, bumped up from mild drought last month, Rebecca Tepper, secretary of the Massachusetts Executive Office of Energy and Environmental Affairs, said on Friday.'
— New Bedford residents turn out to protest proposed waste transfer station by Brooke Kushwaha, The New Bedford Light: 'More than 50 people gathered at the city's Board of Health hearing on a proposed waste transfer station in the North End Thursday evening – with about half of those taking to the microphone to speak out against the project. In the third of four public hearings on the proposal, members of the public shared their concerns around odor, noise pollution, increased traffic, air pollution, and vermin, as well as New Bedford's history of widespread environmental contamination.'
HEARD 'ROUND THE BUBBLAH
ENGAGED — Logan Trupiano, communications director for Mike Kennealy for Governor and former communications director for the MassGOP got engaged to Katie Conese, an environmental scientist at TRC over the weekend. Logan proposed on a boat in Hull Bay. Pic!
TRANSITIONS — Steve Bickerton, the deputy commissioner of Boston's Parks and Recreation department, is moving on after 12 years working for the city. He's joining Morgan Memorial Goodwill as vice president of operations.
HAPPY BIRTHDAY — to state Sen. Jamie Eldridge, Megan Alberto, Dan Wolf, and Axios Boston's Steph Solis.
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