Super PAC places sombrero on Healey

A super PAC supporting Brian Shortsleeve’s campaign for governor is up with digital ads portraying Gov. Maura Healey wearing a sombrero in one and clown makeup in another. The outside group also reported pulling in more than $1 million from companies tied to a real estate firm.

The new ads come as the crowded Republican GOP primary, which aims to select who will face off against Healey in the 2026 general election, ramps up between Shortsleeve, a venture capitalist and former MBTA leader; Mike Kennealy, Gov. Charlie Baker’s former economic development chief; and Michael Minogue, a former medical device executive and major Donald Trump donor.

The pro-Shortsleeve super PAC, named Commonwealth Unity, earlier this week filed a report with campaign finance regulators that showed the outfit raised just over $1 million in just four months.

Half a million dollars came from 11 companies tied to Carruth Capital, according to a review of the filing and online records available from the secretary of state’s corporations division. The company names varied, from Computer 3400 LLC to Ten Bear LLC.

Carruth Capital, a Westborough-based commercial real estate firm, did not immediately return requests for comment Wednesday. Christopher Egan, the company’s president, is a longtime GOP donor and the son of EMC Corp. cofounder Richard Egan.

The super PAC reported spending $34,000 on digital advertising and production costs.

One of its ads features a doctored Healey image, riffing off types of outfits available at the Spirit Halloween store. In the image, Healey is shown wearing a sombrero and poncho while holding a bag of cash. The ad says the costume includes “Free Hotels for Migrants,” “Illegal Immigrants,” and “Solar Panels.”

Another ad overlays clown makeup over Healey’s face, with the text, “Foolish Leadership. That’s Maura Healey.”

Lydia Goldblatt, who has worked for Gov. Mitt Romney and Sen. Scott Brown, is chairing the super PAC. She did not respond to a request for comment Wednesday, but told MASSterList in August that her group is “committed to holding Governor Healey accountable and independently supporting Brian Shortsleeve to bring common sense, conservative management to Massachusetts.”

The super PAC action is sure to ramp up. Another outside group, calling itself Massachusetts First, declared it was supporting Minogue in paperwork filed with the state Office of Campaign and Political Finance last week. The Boston Herald reported its chair is Rob Neuner, the CEO of a Connecticut-based company and a donor to both campaign committees linked to President Trump and former Boston mayoral candidate Josh Kraft.

Healey can probably expect her own super PAC support as Election Day draws closer. In the 2022 race for governor, several outside groups tied to unions supported her candidacy.

Officials at the Massachusetts Democratic Party have been fielding media inquiries on behalf of Healey’s reelection effort. Asked about the super PAC ads, party chairman Steve Kerrigan took aim at Shortsleeve’s time at the MBTA. “No amount of MAGA money is going to trick the voters who know Brian Shortsleeve failed at the head of the MBTA and know he’s going to be at Donald Trump’s beck and call as governor,” he said in an emailed statement.

Are you working on a super PAC that plans to be involved in the 2026 race for governor? Drop me a line: gin@massterlist.com.

HAPPENING TODAY

9:00 | CommonWealth Beacon hosts “The pull — and pain — of Boston street gangs,” a conversation about the era of violent Boston street gangs in the late 1980s to early 1990s and the lessons that can be drawn from it. Doors open at 8:30 a.m. | Boston Foundation, 75 Arlington Street, Boston | Tickets & Agenda

10:00 | Rep. Lori Trahan hosts a virtual press conference with Massachusetts-based experts who will speak about the One Big Beautiful Bill Act’s impacts on Medicaid and the prospect of extending the Affordable Care Act’s premium tax credits, which help people afford health insurance coverage. Other participants include Massachusetts Health Connector Director Audrey Morse Gasteier, Massachusetts Health & Hospital Association Executive Vice President Valerie Fleishman, and local family physician Dr. Manju Mahajan. | Access

12:00 | Gov. Maura Healey provides an update on enforcement efforts related to illegal street takeovers and car meetups. Joined by State Police Colonel Geoffrey Noble. | Room 157, State House, Boston

WU PLANS ‘STATE OF SCHOOLS’ SPEECH

The Boston editor and journalist Peter Kadzis once noted that the late Mayor Tom Menino’s schedule was built around three annual speeches: the state of the city and addresses to the Boston Municipal Research Bureau and the Greater Boston Chamber of Commerce.

Michelle Wu, who interned for Menino before winning a City Council seat and then the mayor’s seat, is looking to rework that schedule.

Appearing Wednesday on the local online chat show “Java with Jimmy,” Wu said over the last year she has reviewed the schedule of “big speeches.” Wu noted she declined to give the annual speech in April to the Boston Municipal Research Bureau after she said the business-backed group mischaracterized municipal finances amid opposition to a property tax shift proposal. (Lt. Gov. Kim Driscoll filled in at the last minute.)

In its place, a “State of the Schools” address on investing in public education is happening later this month, Wu said.

The speech is set for Tuesday, Oct. 28, at 7 p.m. at the Josiah Quincy Upper School in Chinatown, according to the mayor’s office. “I look forward to delivering this first ever State of the Schools address to showcase the work of our school communities and invite our entire city in pushing forward progress for our young people and families,” Wu said in a statement.

KOH, BELSITO JUMP INTO SIXTH CONGRESSIONAL RACE

Did you get a call from Dan Koh yesterday? The former Biden administration official was working the phones as he readied a bid for the Sixth Congressional seat, which is open in 2026 due to Seth Moulton running against U.S. Sen. Ed Markey.

Koh launched his campaign, his second after a 2018 run for Congress, on Thursday with a two-minute video. President Trump figures prominently in the video, as Koh says he’ll stand up to the administration as he has on podcasts and Fox News since leaving the White House. “We can’t roll over and let this nightmare continue,” Koh says.

Koh is expected to quickly raise a seven-figure sum and pull in a slew of endorsements, including from unions, with help from his former boss Marty Walsh, a labor leader and former mayor of Boston.

The field is still in formation. Last night, former state lawmaker Jamie Belsito, who has previously campaigned for Moulton’s seat, said she’ll be taking another run at it, according to the Eagle-Tribune’s Christian Wade.

FROM BEACON HILL

NO REVENUE ADJUSTMENT: Gov. Maura Healey’s budget chief says he is ready to recommend midyear budget cuts if necessary, but for now, the estimate for state tax collections won’t be changed. – State House News Service

SERVICE PLAZA SAGA: State transportation officials are hitting the restart button on finding a new operator to oversee 18 highway service plazas. – Boston Herald

GRASP ON GEOGRAPHY: Beacon Hill leaders mocked President Trump’s comments about moving the 2026 World Cup matches out of Boston, since the matches are taking place in Foxborough. “He should check his geography,” House Speaker Ron Mariano said. Trump also does not have the legal authority to move the matches. – Boston Globe

COMPETITIVENESS COUNCIL: Mark Nunnelly, who served as revenue commissioner and technology services and security secretary under Gov. Charlie Baker, is co-chairing Gov. Maura Healey’s advisory council on competitiveness. Harpoon Brewery’s Dan Kenary is the other co-chair. – State House News Service

DiZOGLIO V. CAMPBELL: State Auditor Diana DiZoglio, who is feuding with Attorney General Andrea Campbell over enforcement of a voter-approved audit of the Legislature, encouraged her to sue the auditor’s office for information related to the audit. – Boston Herald

NEWS NEXT DOOR

EVERETT ABDUCTION: Obtaining straight answers from the U.S. Department of Homeland Security and the Immigration and Customs Enforcement about the abduction of an Everett teenager proves to be a tall task. – The Handbasket

NEW SUBWAY CARS: Shipments of new Red and Orange Line cars appear set to resume after running into a Trump administration roadblock. – Contrarian Boston

MASS FOR JOAN KENNEDY: Members of the Kennedy family, including RFK Jr., were in downtown Boston for a Catholic Mass for Joan Kennedy, mental health advocate and the first wife of the late Sen. Ted Kennedy. – WBUR

BOSTON OFFICE: The Boston office market is showing signs of a recovery, with downtown’s vacancy rate dipping and asking rents rising overall. – Boston Business Journal

SIGN OF MOVEMENT: Construction will cause the repositioning of the iconic Citgo sign in Kenmore Square. – CBS Boston