Inside the lion’s den

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Gin here, welcoming you back. It’s Thursday during one of the (allegedly) quietest weeks of the year. Many thanks to Chris Lisinski and Ella Adams stepping in while I was away for several days. Let’s dive into one of my favorite topics, the Boston mayoral race.

A Boston City Hall wag once compared the challenge of running against an incumbent mayor to venturing inside a lion’s den while wearing porkchop undergarments.

Josh Kraft, who is challenging Mayor Michelle Wu, put it somewhat differently this week. “I’m going against the power of incumbency, okay?” he told GBH’s Boston Public Radio. “A sitting mayor has not lost since 1949.”

That may be partly why he’ll consider a loss by 15 points or less in the Sept. 9 preliminary a win, as he recently told Bloomberg. But on GBH, he was answering a question from co-host Jim Braude about how much more he was willing to spend on the campaign, after already funneling millions of dollars into his run. “If we’re going to give people an honest choice, yeah, I have to loan myself money,” he said, before adding he didn’t yet know how much more. “I’ll decide when I decide.”

During Tom Menino’s time in City Hall, there was a wariness of a Bloomberg-type – the billionaire, not the aforementioned financial media giant he built – coming in and bombarding voters’ TVs with ads. Kraft has done that. One company that works for his campaign specifically directed WBZ-TV to run one 30-second ad full-throttle on Aug. 8 as the Tom Brady statue was unveiled at the Kraft-owned Gillette Stadium.

The spending has been an asset that Wu has sought to turn into a liability, accusing him of trying to buy the election and noting his father Robert’s ties to Donald Trump. Josh Kraft has hit back by trashing Trump and calling Wu “hypocritical” because she backed a self-funded campaign by Shannon Liss-Riordan for attorney general in 2022.

But with less than two weeks to go until the preliminary, Kraft still has “lots of ground to make up,” a recent Boston Globe headline noted. The campaign holds out hope the city’s voters are just tuning in. “While insiders have been talking about the mayor’s race for months, most voters have been focused on other things and are just starting to pay attention to it,” Kraft senior adviser Will Keyser told the newspaper.

Insiders have actually been talking about the race for nearly two years, after Kraft moved to Boston and registered to vote in late 2023. They’ve closely watched the twists and turns, and some hit the panic button after Kraft’s April appearance on WCVB. An attempt by some to coax developer Tom O’Brien into the race was unsuccessful. (Interestingly, O’Brien was among the bold-faced names spotted at this week’s South Boston fundraiser for Wu.)

After the last mayoral prelim four years ago, Wu crossed the City Council chamber and brokered a deal with the other finalist, fellow councilor Annissa Essaibi George, to keep the campaign as positive as possible. That’s unlikely to happen again this time. The 2025 race has been negative since the start, with name-calling on both sides.

Asked about that in her own GBH radio appearance earlier this week, Wu said, “Boston politics is not for the faint of heart, and name-calling is nothing new in my day-to-day job, believe me. I don’t mind it.”

Or put somewhat differently: Welcome to the lion’s den.

What do you think the Sept. 9 preliminary margin between Wu and Kraft will be? Send your guesses to: [email protected].

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MassDOT is rushing a secretive 35-year lease with Applegreen, despite inflated numbers, weak financials, and better alternatives. KPMG flagged serious flaws, yet the deal moves forward. Public oversight is missing, and $900M in rent is at risk. Legislators must act now. Before signing away public assets for decades, the MassDOT Board must pause and review. Learn more.

HAPPENING TODAY

5:15 | Amtrak President Roger Harris will be available for interviews as the first NextGen Acela train departs Boston for Washington, D.C. | South Station, Boston

10:00 | Boston Mayor Wu will share the findings of the independent review into school transportation safety policies and performance | Bruce C. Bolling Municipal Building, 6th Floor, 2300 Washington Street, Roxbury

11:00 | Mass. State Lottery hosts a Summer Cash Bash. Treasurer Deb Goldberg attends. | 135 Gold Star Blvd., Worcester

2:00 | Massachusetts Seal, Flag, and Motto Advisory Commission meets. The agenda includes an update from co-chairs and a review of finalists. | Agenda and Zoom

POLITICAL INTEL

Joe Caiazzo, a political consultant who has worked for Bernie Sanders and Rhode Island Sen. Sheldon Whitehouse, earlier this summer signed on with Rep. Seth Moulton. The Salem congressman’s campaign account sent $20,000 to Caiazzo’s firm back in May. Moulton’s ambition – he previously ran for president and clashed with Nancy Pelosi – has created everlasting buzz that he’s seeking higher office, with the U.S. Senate seat held by Ed Markey on the list. Moulton, who does have a Democratic primary opponent, has also skirmished with Gov. Maura Healey over transgender athletes. Caiazzo, who lives in Moulton’s district, declined comment….

…WBUR’s state politics reporter Walter Wuthmann leaves the station at the end of this month. The Bowdoin College graduate, who previously worked at a weekly in Maine and an English-language newspaper in Sri Lanka, is moving down to New York City to be closer to family and start his next chapter in journalism. His stories for WBUR are worth perusing here….

…Plenty of boats are floating in Boston Harbor these days, taking advantage of the New England summer. But one 282-foot super yacht off Long Wharf is hard to miss, thanks to it sporting an eye-catching “Z” inside a Superman shield. The luxury yacht, called “Man of Steel” and previously owned by Steven Spielberg, appears linked to Barry Zekelman, a Canadian billionaire and Donald Trump supporter. An emailed inquiry to his company, Zekelman Industries, was not immediately returned.

FROM BEACON HILL

BROKER FEE WORRIES: With the big “move-in day” approaching, the first one under the new state law on broker’s fees, some advocates and renters are concerned about how the law, signed by Gov. Maura Healey, will be enforced. – GBH News

TOMPKINS TAKES LEAVE: Suffolk Sheriff Steve Tompkins took a “medical leave” while facing extortion charges, as Gov. Maura Healey and Attorney General Maura Campbell announced a special sheriff will step in to run the law enforcement agency overseen by Tompkins. – Boston Herald

TECH PRIVACY: Tricia Farley-Bouvier, the House chair of Beacon Hill’s advanced information and technology committee, wants players in the artificial intelligence industry to look to privacy protections. – State House News Service

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NEWS NEXT DOOR

KENNEDY DYNASTY: The Kennedy family is now so large it’s become more of a holding company than a biological family, according to a new in-depth report. But there has been a loss of cohesion since the 2009 death of Ted Kennedy, and it’s been on display with RFK Jr.’s jump to Donald Trump. – New York magazine

STATE POLICE RECRUIT: According to an autopsy released to State Police recruit Enrique Delgado-Garcia’s family, the young man died after a boxing match due to blunt force injuries to the head. – MassLive

BOARD CHAIR: Quincy Miller, Eastern Bank’s president and COO, is the new chair of the board of directors for the New Commonwealth Fund, the nonprofit focused on racial equity and social justice. – Boston Business Journal

IN MEMORIAM: Marie Turley, an advocate for gender equity and Mayor Tom Menino’s adviser on women’s issues, has passed away. She was 76. “I am heartbroken that we will never see Marie Turley at a canvass kick-off, around the decision-making table, at a Women’s Day Breakfast, or mentoring a young person who aspires to civic engagement again,” Congresswoman Ayanna Pressley wrote on social media. – Twitter/X

POLICE OVERSIGHT: While the Boston Office of Police Accountability and Transparency has sustained citizen complaints, Police Commissioner Michael Cox routinely rejects their recommendations. – WBUR

GLOBE EDITOR: Jennifer Peter, the Boston Globe’s managing editor, is the next editor-in-chief of the nonprofit Marshall Project, which reports on criminal justice issues. – Media Nation

ENFORCEMENT TECH: A majority of Boston city councilors voted against approval for use of social media surveillance tools by the Boston Regional Intelligence Center (BRIC). – The Flipside

MORE HEADLINES

Local candidate for national actors’ union under fire for social media posts

Josh Kraft: $6.3M income in 2024 came from ‘the family business’

Audit finds education department failed to property investigate reports of alleged teacher misconduct

Mass. close to eradicating invasive Asian longhorned beetle

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