Why you should care

Because the next Elizabeth Warren could be waiting in the wings.

The sport: lawyering. The skill: negotiating reporters while maintaining a political charm. The game: Today, it’s a set of gray-area laws surrounding fantasy sports betting — is it gambling?

The star player: Massachusetts Attorney General Maura Healey, who is equipped with the moves to win many an event — athletic, intellectual, public policy or otherwise. Healey, just a year into her term and serving for the first time in elected office, is already being touted by some as a possible heir to Elizabeth Warren. A former star basketball player who touts her woman-of-the-people credentials as much as possible, Healey is also the first openly gay attorney general in America, an epithet that has earned her some additional progressive head nods. “We’re incredibly aggressive,” she tells OZY — which is her key narrative, a go-getter on behalf of the people. It’s a story that’s worked, apparently. Proof: Healey shocked party figures by crushing Warren Tolman, a longtime progressive insider, nearly 2-to-1 in her 2014 primary, and then beat her Republican opponent just as handily in the general.

But before we get ahead of ourselves, there’s Healey’s current gig, an important one here in Massachusetts, where Healey’s predecessors enjoyed favorable reputations as button pushers and unabashed go-getters. Healey has tried to make this her M.O. as well. In Year 1, she sued one of the state’s largest debt collecting law firms; in her first month, she butted heads with Partners Healthcare, one of Boston’s largest companies and the machine behind Brigham and Women’s Hospital and Mass General, when she pressured a Superior Court judge to nix a property grab that she said violated antitrust law. (Partners did not respond to a request for comment.) “She hasn’t been afraid of controversy,” says Mo Cunningham, a University of Massachusetts Boston political scientist. He adds that she’s even taken on political risk to do so. “If you’re going to be aggressive the way Healey is, sometimes you’re going to tick people off.”

Despite her political newbie status, Healey has lived and breathed the law for 16 years. Her biggest bragging point is from her earlier days: As chief of the attorney general’s civil rights division, she led Massachusetts’ winning arguments in America’s first lawsuit against the federal Defense of Marriage Act in 2007; that decision even got a shout-out in the Supreme Court’s majority opinion to strike down the country’s ban on gay marriage last summer. “At the time, it was unprecedented,” she remembers.

Healey’s narrative is a broad one — essentially: I’m just like you, one of the gals! She brought me today to a homeless shelter, where she serves the city’s down-and-out a meal of cordon bleu. She recounts her early days before her years as a junior partner at the prestigious law firm Wilmer Hale, before Harvard: In third grade, Healey shadowed an attorney, insistent even then that she would be a lawyer. A grainy black-and-white photo of Healey and that lawyer plays prominently in one of her ads.

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Maura Healey joins Senator Anthony Petruccelli, left, for Election Day lunch in November.

Source The Boston Globe via Getty Images

But it wasn’t straight to the stacks of the law library after college. First, the 5-foot-4 Healey took a detour overseas to play for UBBC Wüstenrot Salzburg, a professional basketball team in Austria. (In Healey’s first campaign video, she spins a basketball on her finger, swishes a few jump shots and finishes by saying, “The big guys have plenty of lawyers; the attorney general’s job is to fight for the rest of us.”)

Post b-ball, Healey went to Northeastern law school, where she came out and studied under Reginald Lindsay, a Clinton-appointed federal judge, who reinforced for her the idea of government’s role in securing the rights of minorities. Born in Birmingham, Ala., under Jim Crow laws and desegregation, the African-American Lindsay was also wheelchair-bound and faced discrimination on both accounts. “It made me really mindful of the importance of civil rights,” Healey says. After graduating in 1998, her first job was as a clerk for U.S. District Court Judge A. David Mazzone, who famously ordered the cleanup of Boston Harbor in the ’80s, and it taught her “the good force” that law could be.

Just about the only way to throw off the normally unflappable Healey is to suggest that her office hasn’t embraced its activist persona enough to make that good force a reality. “If you’re a liberal, she’s been kind of disappointing,” says Thomas Whalen, a political scientist at Boston University. “She doesn’t want to step on anyone’s toes.” Whalen figures Healey has a tough job, playing cop while her own party holds political power. “As long as she doesn’t rock the boat,” he says, “she has a chance to make it to the next level.” (Healey is indignant. “If anything, I’ve been talked about as incredibly active,” she says.

But late last year, Boston Globe columnist Joan Vennochi wondered why Healey hadn’t cracked down more on fantasy sports betting. Healey’s compromise, finalized in March: Allow them to operate, but impose restrictions based on age (21 or over only) and competitive level (betting on college sports is off limits). Vennochi suggested it had to do with the fact that New England Patriots owner Robert Kraft is an investor in DraftKings, a top company in the field. Which might make this particular game a tricky one, pitting Healey’s elements against one another — the great athletic love of Boston’s common man, and a promise to fight for that same common man.

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