 | BY LISA KASHINSKY AND KELLY GARRITY | Presented by |  |
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| UP IN THE AIR — It’s trial balloon season in the Boston mayor’s race. And Michelle Wu is floating above it all. Nearly everyone thinks Wu is running again , and the mayor herself has hinted at it. But the longer she waits to kick off her campaign, the longer she keeps the scrutiny on her would-be opponents. The Boston Globe’s recent parade of pieces on Josh Kraft mulling a mayoral bid (first reported by CommonWealth Beacon’s Gintautas Dumcius six months ago) elevated his possible run from the realm of insider chatter to the broader public lexicon. And that will set him up for closer inspection months before he’s likely to make a decision on the 2025 race. Mixed signals abound about William Gross , the former police commissioner who backed Annissa Essaibi George against Wu in the last mayoral race after passing on a bid of his own. He reemerged earlier this spring at a rally with restaurateurs in the North End, where PR guru George Regan stood to the side and yelled “run for mayor.” But Gross insisted to Playbook he’s not interested . Regan, meanwhile, is the spokesperson for the restaurant group clashing with Wu over outdoor dining restrictions, one of the leaders of which, Jorge Mendoza-Iturralde, now says he’s running against her . Perennial candidate Althea Garrison also plans to give the mayor’s race a go, per Dumcius. Suffolk District Attorney Kevin Hayden has been approached about running, but is uninterested, according to a person familiar with the conversations. While some people want Attorney General Andrea Campbell to make another run for the post, she told Playbook: “I love my job and I am not running.” Then there’s Ed Flynn, whose turn from being the City Council’s peacekeeper to its primary antagonist has baffled several of his former colleagues and much of Boston’s political chattering class. Flynn insisted to the Herald that his recent meeting with North End restaurateurs — in which he violated council norms by crossing district lines — was not a sign of mayoral ambitions , only to turn around and tell The Globe that any talk of his 2025 intentions are “premature.” He later told Playbook “now is not the time for politics and campaigns” and that he’s “focused on providing positive leadership” to constituents. The Navy veteran has openly signaled that he’s interested in continuing his public service in a non-elective capacity — veterans affairs, specifically. He also has a family legacy to protect. On paper, Flynn is well positioned for a mayoral bid. He’s got experience, a proven ability to fundraise, a well-known surname and a megaphone in the pages of the Herald. Kraft, too, would have personal wealth and a family name to trade on. But history is on the incumbent’s side. So are other factors. Wu has kept up a steady cadence of fundraisers since she took office, including events around the Lunar New Year and Earth Day, her annual “Women for Wu” reception earlier this week and some smaller events planned for the summer, according to a person familiar with her schedule. She started June with nearly $1.5 million in her war chest — double what Flynn had on hand. Plus, unless someone else emerges , progressives miffed by Wu governing more moderately than they had hoped don’t have much other choice (Kraft, if he runs on the left, could face difficulty distancing himself from his family’s association with Republican former President Donald Trump). And so, for now, it’s advantage: Wu.
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Michelle Wu celebrates her election in 2021. | Josh Reynolds/AP | GOOD FRIDAY MORNING, MASSACHUSETTS. Lisa here, for the last time. Writing this newsletter over the past three years has been the opportunity of a lifetime. We’ve been through a lot together — a pandemic, a series of historic elections and a few terrible Patriots seasons — and I’ll deeply miss the community we’ve built here. Thank you for welcoming me into your inboxes each morning, for sending me your tips and scoops and for dealing with my incredibly late night and very early morning phone calls. To my editors — and there have been too many of you to name — thank you. To my co-authors over the years — Madison, Sophie and Mia — you’re all rock stars. And to Kelly — who loves an em-dash even more than I do — I can’t wait to see how you make Massachusetts Playbook your own. Like I said last week, I’m not going far. While the presidential race will now be my main focus for POLITICO, I’ll still be based in Boston and covering politics in Massachusetts, New Hampshire and across New England. So please, don’t be a stranger. I know I won’t be.
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Playbook runs on Dunkin', even if I don't run it. | TODAY — Gov. Maura Healey , her partner, Joanna Lydgate , Sens. Elizabeth Warren and Ed Markey , Rep. Stephen Lynch and U.S. Energy Secretary Jennifer Granholm tour Trillium Brewing Company at 2:30 p.m. Healey speaks at the Winnacunnet High School graduation ceremony at 6 p.m. in Hampton, New Hampshire. Lt. Gov. Kim Driscoll speaks at the Massachusetts School of Law commencement ceremony at 5 p.m. in Wilmington and attends a GreenRoots event at 7 p.m. in Chelsea. Markey is on WBUR’s “Radio Boston” at 11 a.m. and joins Rep. Bill Keating for an update on the Cape Cod bridge project at 11:30 a.m. in Bourne. Warren visits Kam Man Food Marketplace at 11 a.m. in Quincy. Wu hosts a coffee hour in Chinatown at 9 a.m., speaks at the Asian Community Development Corporation dim sum breakfast at 11 a.m. and gives remakes at a Caribbean flag raising ceremony at City Hall at 1 p.m. THE WEEKEND — MassDems Chair Steve Kerrigan is on WBZ’s “Keller @ Large” at 8:30 a.m. Sunday. Boston Chief of Economic Opportunity and Inclusion Segun Idowu is on WCVB’s “On The Record” at 11 a.m. Sunday. Auditor Diana DiZoglio is on NBC10 Boston’s “At Issue” at 11:30 a.m. Sunday. PLAYBOOK MEET AND GREET — Looks like you all really want to meet the Massachusetts Playbook team! We’ve had more people sign up for our June 12 event at Carrie Nation than we can accommodate. Please email Lisa at lkashinsky@politico.com or Kelly at kgarrity@politico.com if you’d like to be added to the wait list. We’ll send out confirmation emails, which will be required for entrance, next week.
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| | A message from Choose Who You Use: A new study published earlier this year revealed that if customers chose a retail electric provider over a utility in 2022 and 2023 the combined savings would have been $1.7 billion. Join the Choose Who You Use coalition to protect electricity choice and preserve Massachusetts ratepayers’ ability to choose the most affordable, renewable options for them. Learn more. | | | |  | PARTY POLITICS |
| EXCLUSIVE — State Rep. Christopher Worrell will be the lone uncommitted delegate among Massachusetts’ 124-person Democratic National Convention contingent this summer. The first-term lawmaker from Boston, who is Black, said “it is important that the voices of Black and Brown people are heard and our votes are never taken for granted.” The free-agent slot comes after activists staged an 11th-hour effort to get Democratic presidential primary voters to select “no preference” on their March ballots to protest President Joe Biden ’s handling of the war in Gaza. While the total, just over 9 percent of the vote , fell short of the 15 percent needed to win any delegates statewide, the count was high enough in Rep. Ayanna Pressley ’s congressional district to secure an uncommitted delegate. Worrell was selected for the role at a district caucus in Dorchester in April. “Every day, my heart breaks for the tragedy that is taking place in the Middle East,” Worrell told Playbook. “The human toll has been horrific and it needs to stop. The killing needs to stop. There needs to be a lasting cease-fire. Hostages need to be freed. There needs to be a lasting two-state solution. And [Prime Minister Benjamin] Netanyahu needs to go.” Worrell wouldn’t share how he plans to vote when it comes to the party's nominee. But he said he is “100 percent committed to defeating Donald Trump in November.” Activists behind the Vote No Preference Coalition hope he at least brings the cease-fire message to Chicago.
| | DATELINE BEACON HILL |
| NEW THIS MORNING — Gov. Maura Healey joined our colleague Steven Overly on the POLITICO Tech podcast to talk about her plan to pour $1 billion into the climate tech sector over the next decade — plus any money she gets from Biden's administration — and why she fears a second Donald Trump presidency could undermine it all. “Donald Trump has surrounded himself by people who are only interested in furthering the power of oil and gas and the fossil fuel industry, which is the industry that's gotten us into this in the first place,” Healey told Overly. “That's not a world I want to go back to. And it's certainly a world that Donald Trump lives in.” Healey, a surrogate for Biden’s reelection campaign, also said climate is “certainly a distinction” between the current and former presidents that “we need to continue to draw.” Listen to the interview here. — “Healey admin awards $3.4M to help grow Mass. ‘climate workforce’,” by John L. Micek, MassLive. — “Bill to allow campaign funds for childcare on the move,” by Michael Jonas, CommonWealth Beacon.
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| | THE GOLD STANDARD OF POLICY REPORTING & INTELLIGENCE: POLITICO has more than 500 journalists delivering unrivaled reporting and illuminating the policy and regulatory landscape for those who need to know what’s next. Throughout the election and the legislative and regulatory pushes that will follow, POLITICO Pro is indispensable to those who need to make informed decisions fast. The Pro platform dives deeper into critical and quickly evolving sectors and industries—finance, defense, technology, healthcare, energy—equipping policymakers and those who shape legislation and regulation with essential news and intelligence from the world’s best politics and policy journalists.
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| CELTICS WIN — Only three more W's to go before Boston Mayor Michelle Wu is feasting on some Texas brisket (and Dallas Mayor Eric Johnson is eating his words). More on their friendly food wager from The Globe . — “Boston city councilor ‘skeptical’ that costly capital projects will be completed,” by Gayla Cawley, Boston Herald.
| | YAHD SIGNS AND BUMPAH STICKAHS |
| CASH DASH — Former Gov. Charlie Baker is headlining a fundraiser for (a far friendlier to him) MassGOP later this month, according to an invitation obtained by Playbook. Outgoing Republican National Committeeman Ron Kaufman will also be honored at the Lincoln Reagan Reception on June 26. Tickets range from $250 to $5,000.
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| | A message from Choose Who You Use:  
| | | | | WARREN REPORT |
| — “Jamaal Bowman Lands Endorsement From Elizabeth Warren,” by Nicholas Fandos, The New York Times: “Senator Elizabeth Warren of Massachusetts waded into one of the nation’s most contentious House primaries on Thursday, extending a lifeline to an endangered ally on the left."
| | MARIJUANA IN MASSACHUSETTS |
| — “Marijuana Regulators Look To Preserve Island Access,” by Noah Glasgow, Vineyard Gazette : “State cannabis regulators came to the Island Thursday to hear from local cannabis producers, retailers, and medical and recreational consumers who say that a ban on the transport of cannabis by ferry will put the Island’s legal cannabis sellers out of business.”
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| | JOIN US ON 6/12 FOR A TALK ON THE AIRLINE INDUSTRY : As air travel soars again, policymakers and airlines are grappling with a series of contemporary challenges to the industry's future. Join POLITICO on June 12 for a topical and timely conversation with government leaders and aviation stakeholders about the state of the airline industry. From what passengers want to what airlines need amid the high demand for air traffic, workers and technology solutions. What can Washington do to ensure passengers and providers are equipped to fly right? REGISTER HERE . | | | | | | | FROM THE 413 |
| — “Springfield school chief resigns amid mounting criticism of his disparaging remarks,” by Aprell May Munford, The Springfield Republican; and Elizabeth Romȧn, NEPM: “The superintendent of Springfield Public Schools served his last day on the job Thursday, leaving a few weeks short of his planned retirement, after school and city officials reacted with outrage to disparaging comments he made this week, in a private conversation, about Springfield leaders. The resignation came after a morning press conference at which the main target of Superintendent Daniel Warwick’s comments, Latonia Monroe Naylor, defended herself and her family.”
| | THE LOCAL ANGLE |
| — “Top Quincy official was fired. Now, the feds are involved, the mayor says,” by Peter Blandino, The Patriot Ledger: “Federal investigators are presenting evidence to a grand jury of alleged ‘financial irregularities’ undertaken by former Director of Elder Services Tom Clasby, according to Mayor Thomas Koch, who said he learned of the development through sources.” — “Regulators explore impact of hospital 'greed',” by Christian M. Wade, The Eagle Tribune: “[Amid the Steward Health Care meltdown, the] Federal Trade Commission, U.S. Department of Justice, and Department of Health and Human Services have launched an investigation into the ‘impact of greed’ in health care and plan to review details of recent transactions the agencies say may be harming patient health, worker safety and the quality of care for patients.”
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| | A message from Choose Who You Use: Massachusetts’ utility customers have recently seen some of the highest electric rates in the country, but customers who chose retail electric providers could have saved hundreds of dollars over the last two years. The last thing we should be doing during this moment is eliminating this choice for Massachusetts consumers and forcing people to live under monopoly utility service.
Choose Who You Use is committed to protecting real electricity choice in Massachusetts. We believe the power to choose energy should be in the hands of the people. In Massachusetts, individuals should be able to choose the type of energy they want and how to pay for it. Learn more. | | | | | HEARD ‘ROUND THE BUBBLAH |
| SPOTTED — at Boston City Councilor Sharon Durkan 's fundraiser at Cornwall's last night: Boston Mayor Michelle Wu , state Rep. Jay Livingstone , BHA leader Kenzie Bok and Suffolk SJC clerk candidate Allison Cartwright . OOPS — To those who were bombarded with happy birthday texts Thursday, our apologies. Hope people are just as generous with their well-wishes today! With that ... HAPPY (BELATED) BIRTHDAY — to Grace Ross, Donna Fenn, Jen Hemmerdinger, Elvira Mora and Christopher Rowland, Washington Post reporter and former Boston Globe Washington bureau chief. Happy very belated to state Sen. Adam Gomez and Robert Kraft. HAPPY BIRTHDAY (AGAIN) — to state Rep. Aaron Michlewitz, chair of the House Ways & Means Committee; former state Rep. and past Cambridge City Councilor Tim Toomey; Kevin Sprague, Sema Emiroglu and Isaac Luria. HAPPY BIRTHWEEKEND — to Zayda Ortiz of Progressive Mass, Joseph Prezioso, Bill Douvris, Ben Case, Dan Futterman, Michael Vallarelli, David Ciampi and Hailey Reed, who celebrate Saturday; and to Sunday birthday-ers FEMA Region I Administrator and former state Rep. Lori Ehrlich, Calla Walsh, Sheila Ramirez, Jeff Solnet, John Dukakis, 90 West’s Harry Shipps and Kelsey Perkins, district director for Rep. Katherine Clark. NEW HORSE RACE ALERT: LISA’S LAST RODEO — Host Lisa Kashinsky hops in the saddle one last time to talk politics and polls with hosts Steve Koczela and Jennifer Smith. This wide-ranging episode covers #mapoli’s reactions to Donald Trump ’s guilty verdict and Joe Biden ’s border action, as well as new poll numbers on the state’s top politicians. Subscribe and listen on iTunes and Sound Cloud . Want to make an impact? POLITICO Massachusetts has a variety of solutions available for partners looking to reach and activate the most influential people in the Bay State. Have a petition you want signed? A cause you’re promoting? Seeking to increase brand awareness among this key audience? Share your message with our influential readers to foster engagement and drive action. Contact Jesse Shapiro to find out how: jshapiro@politico.com . | |
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