As word spreads that Alan Leventhal, a former US ambassador to Denmark and founder of a Boston-based real estate firm, is mulling a run for governor, here’s some free advice for rich men who seek meaning in life beyond money.
Be wary of political consultants and PR experts who tell you there is a path to victory over an incumbent politician in Massachusetts.
Josh Kraft, a son of Robert Kraft, the billionaire owner of the New England Patriots, just found out how hard that path is to find. After spending at least $5.5 million of his own money to win 21,324 votes in Boston’s preliminary race for mayor earlier this month, he dropped out of what was euphemistically called a race but turned into a rout by Mayor Michelle Wu. After the collapse of his campaign, my colleague, Shirley Leung, put together a funny whodunit list of who might have played a role in convincing Kraft, a political neophyte, to challenge Wu, a political maestro.
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One prime suspect was PR honcho George Regan, whose longtime client, New Balance chairman Jim Davis, put $1 million into a super PAC that supported Kraft. Davis might want to think twice before he signs onto Regan’s latest shadow project — promoting Leventhal, a wealthy businessman and philanthropist, as a candidate for governor.
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In August, the Boston Herald reported that Leventhal was considering such a run, with a quote from Regan saying, “He’s disappointed in the lack of leadership in the state and city. Alan loves this state and city and is looking to help.” When I tried to reach Regan on Tuesday to talk about Leventhal, his office told me “George is in Italy at the moment with limited cell reception.” Ciao, George.
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Campaign consultant Will Keyser was also cited as a person of interest when it came to persuading a political newcomer like Kraft to run against Wu, an avid practitioner of the tough politics championed by her mentor, the late mayor Tom Menino. After their split with Kraft a week before his crushing loss to Wu, Keyser and his wife, Eileen O’Connor, who make up Keyser Public Strategies, put out word that they knew the path was hard and it would take an A-plus candidate to make a real fight of it.
Meanwhile, as that duo processes their former client’s loss, consultant Doug Rubin is “assisting Leventhal,” according to a report by Gintautas Dumcius for MassterList. It’s unclear exactly what that means, since Rubin told Dumcius that he had not been retained by anyone in the 2026 race for governor. On Tuesday, Rubin told me the same thing, and repeated it on Wednesday. Rubin previously advised Stephen Pagliuca, a businessman and onetime Celtics co-owner, who ran unsuccessfully for US Senate in 2009.
When it comes to assisting Leventhal, Rubin is likely telling him there is a plausible path for a potential run as an independent against Governor Maura Healey. He is probably saying that on the national level, voters are unhappy with the national Democratic brand and that in Massachusetts, voters like Healey but don’t love her. That there is frustration with one-party dominance on Beacon Hill, as evidenced by last year’s vote to endorse a ballot question that calls for the state auditor to audit the Legislature. And that the right candidate can woo voters who are tired of the status quo.
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But taking on Healey would be difficult for any candidate, especially one like Leventhal, with no built-in political base and little name recognition beyond certain elite business and political circles.
No doubt Leventhal is thinking that his experience in business and real estate will help him promote policies to make Massachusetts more competitive. He also has the financial resources to tell Massachusetts voters who he is and why he should be governor.
But as a veteran political consultant who wants to remain nameless told me: “If [Leventhal] called me tomorrow and said ‘I have $1 million for you,’ I would say, ‘It takes more than money and a desire to do good things to win an election.’ ”
A candidate must be able to say exactly why the incumbent they seek to replace shouldn’t be returned to office and why they are the best alternative. Kraft couldn’t do that. Before he gets into the race, Leventhal should make sure he can.
Even so, a campaign as an independent candidate is an uphill climb. Like Wu, Healey is a skilled politician who has found a comfortable center on economic issues, while carefully choosing her battles against President Trump on social issues. Two Republicans who are vying for their party’s nomination are pushing hard to the Trumpian right, a dubious strategy in a state where Trump is greatly disliked.
Is there a path around Healey for Leventhal? It’s easy for consultants to conclude yes, there is.
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Win or lose, they get paid.
(Some material from the Globe Opinion newsletter, Right, Left, and Center, was used in this column.)
Joan Vennochi is a Globe columnist. She can be reached at joan.vennochi@globe.com. Follow her @joan_vennochi.