Maura Healey’s Trump Card

The state attorney general has sued Donald Trump’s administration more than any other elected official in America—and voters love her for it. But is she playing for Massachusetts’ glory, or her own?

Photograph by Kyle Mercer

It’s a little disappointing, honestly, that Donald Trump hasn’t assigned a cruel, dismissive nickname to Maura Healey. While the Tweeter-in-Chief doles out less-than-affectionate monikers to both sides of the aisle (just ask “Crooked” Hillary Clinton and “Liddle” Marco Rubio), the derogatory pet names have become the ultimate credential of the liberal resistance. Thus far, at least two Massachusetts pols have been so honored. Candidate Trump christened Boston’s mayor Marty “Clown” Walsh way back in 2015, and of course Trump feuded with U.S. Senator Elizabeth “Pocahontas” Warren throughout the 2016 campaign. But few Massachusetts residents seem to be working quite so hard to earn the president’s ire as Healey. So where’s the recognition?

It can only be a matter of time. In fact, it’s hard to imagine that the combative but immensely likable Healey won’t soon land in the Fox News crosshairs, prompting Trump to tweet his displeasure with her, nickname and all. The Massachusetts attorney general, after all, spent just about all of 2017 as a thorn in the side of Trump and his administration. She has brought, by my count, at least 15 lawsuits on issues ranging from immigration, the environment, and healthcare to education and telecommunications. Healey has spoken up or attempted to intervene against Trump’s Environmental Protection Agency, Federal Communications Commission, and Federal Highway Administration, as well as the departments of Energy, Education, Transportation, and Homeland Security. She has opposed his executive orders, his appointments, his budget, and his proposed laws.

“This is a president who is reckless, who has no regard for the rule of law, who does things that actually hurt our residents, hurt our colleges and universities, hurt our healthcare system, hurt our businesses,” she told me in an interview, high up in the One Ashburton building, next to the State House. Healey was equally quick to blast Scott Pruitt, head of the EPA (“dirtier air and water”); Attorney General Jeff Sessions (“misplaced priorities”); Education Secretary Betsy DeVos (“sticking it to students here, and the taxpayers”); and congressional Republicans (“shown a total inability to do anything to stop this mad train”).

Healey’s assault on Trump began before he even took office—within a week of the November 2016 election, she announced the creation of a special hotline for reporting violence or threats motivated by discrimination, which she explicitly linked to fears stemming from Trump’s election. Two days after Election Day, Healey tells me, she started calling other state AGs—primarily Democrats—to discuss, strategize, and coordinate. As of this writing, she was still at it, suing to prevent changes to “net neutrality” regulations, which guarantee equal online access to users.

Even though the grudge match is one-sided, for the moment, Healey’s decision to make herself a chief antagonist to Trump seems like good politics, both in Trump-averse Massachusetts and in national Democratic circles. Just three years after rising from being an obscure assistant AG to win her first campaign, Healey’s approval ratings are comfortably in the mid-60s and she has become a hot-ticket attraction nationally. And that attention grows every time Healey launches a verbal or legal arrow at the Trump administration.

All of which raise the questions: Is Healey using Trump as a convenient political punching bag to raise her profile for higher office? Is she standing up to the White House to protect the citizens of the state? Or is she merely advancing her own ideological and political agenda? And, perhaps most important of all, is there some reason it can’t be a little of all three?

It wasn’t supposed to be like this. When Healey was running in 2014 to succeed Martha Coakley, the expectation was that Coakley would become governor, and in two years a simpatico President Hillary Clinton would replace Barack Obama. Then they would all work together on their shared priorities. Instead, Healey got Republican Charlie Baker in the State House and then Trump in the White House. So where does that leave Healey’s future?

Some Democrats had hoped she would challenge Baker in 2018, but last February she said publicly that she will instead seek another term as attorney general, and she reiterated that intention to me. Healey may make no attempt to hide her antipathy for Trump, but she is far more circumspect about Baker, either out of political calculation, given his immense popularity across the state, or because he has been more cooperative than his Washington party mates. Or again, perhaps a little of both. Asked about her relationship with the governor, Healey cited their work together on opioid prescription legislation and quickly moved on to other topics. If she’d had a change of heart, which some Democrats are still holding out hope for, one assumes she would have had more to say about him.

Not that she’s splashing cold water on the assumption by many, including me, that she will instead run for governor in 2022. “Might there be other opportunities down the road? There might be,” she says coyly. One thing she doesn’t seem likely to do is cash out after this stint in public service, returning to her roots in private-sector law—she spent seven years in commercial and securities litigation at WilmerHale before going to work for Coakley. She’s a rising star in politics, and where she’ll take her talents has become the political talk of the town. Which means that while she could easily run for governor, or for the U.S. Senate when a seat opens up, there could be another avenue: joining the administration of a new Democratic president whom she helps elect in 2020. Don’t be surprised to see Healey picking a favorite in the upcoming presidential nomination battle, and stumping hard for her choice in the crucial New Hampshire primary. (In our conversation, she twice mentioned, unbidden, her New Hampshire roots.) So the question isn’t so much if she’ll move on as “When?” and “To where?”

What isn’t a question is that Healey has a natural political gift—the ability to be simultaneously earnest, charming, and ambitious. Perhaps it’s her pixyish frame, her dimpled grin, or that indefinable spark behind her eyes; I have tried and failed for years to parse why some politicians have “it” and others don’t. All I know is that I’d be uncomfortable with most people leaning toward me from the edge of a chair, staring me deep in the eyes, swamping me with earnest verbiage about her own accomplishments. But Healey I could talk to all day. Likewise, you would think her jokiness and basketball-twirling sense of fun would detract from the gravitas required of a top law enforcer, but it doesn’t seem to.

She’s likely going to need every ounce of her charm and political savvy if she wants to make the leap to a higher office. For unless she earns an appointment from a friendly White House resident—whether as U.S. attorney general, U.S. attorney for Massachusetts, or some other position—she’ll have to contend with a force that has proved ruin to many a rising political star here in Massachusetts: the AG curse.

It would be a wild understatement to say that it’s not easy to go on from being attorney general to winning another statewide office. In fact, the AG’s curse has become one of the most immutable laws of Massachusetts politics. It was last broken in 1966, when a U.S. Senate seat opened up and the then-dominant Republican Party cleared the field for Edward Brooke to claim the nomination unopposed. He went on to easily defeat Democrat Endicott Peabody, who had just been voted out in his own party’s primary after a single two-year term as governor. And Brooke is one of just two people to accomplish the feat since attorney general became an elected office in 1855. Not for lack of ambition, though. Nine of the last 12 state AGs ran for either Senate or governor—two of them, including Coakley, ran unsuccessfully for both.

Part of this can be chalked up to problematic cases having a way of catching up with AGs. Coakley, for example, came to the job after prosecuting cases in Middlesex County, including the baby-murder case of au pair Louise Woodward and the Gerald Amirault abuse case involving the Fells Acre Day Care. Though many praised her for those prosecutions, detractors who blamed Coakley for buying into false claims of shaken-baby syndrome and child-abuse hysteria hammered her during her 2014 gubernatorial campaign. Tom Reilly, who served before Coakley, alienated segments of the voting public by arguing against same-sex marriage in court, and failing to aggressively pursue charges amid the Catholic Church abuse allegations. When Reilly ran for governor in 2006, he finished third (in a field of three) in the Democratic primary. Other times, cases drive a wedge between crucial political figures and their allies, as when Reilly’s predecessor, Scott Harshbarger, prosecuted associates of one of his predecessors, Edward McCormack. Harshbarger felt the sting of every one of those alienated Democrats in 1998, when he lost his challenge to then-Governor Paul Cellucci by roughly three points.

Other cases simply turn potential campaign donors cold; every legal challenge to a corporation makes it harder when it comes time to ask business executives to contribute to your next campaign. So why do so many expect Healey to be immune? One theory is that there is no curse—just a few near misses that make it look that way. Another is that Healey has a much shorter background as a high-profile prosecutor, and as a result has not piled up detractors because of controversial cases. And thus far she has seemingly been spared the types of politically thorny issues that can haunt an attorney general during campaign season. All of which explains why some feel that Healey should have taken her shot right away, by challenging Baker in 2018, before the AG’s duties inevitably start to cost her.

The thing is, you can never count on good luck to last—and she may have just been dragged into her first quicksand case. Within a week of the Boston Globe reporting claims of sexual harassment against Bryon Hefner, the husband of state Senate President Stan Rosenberg, Healey’s office agreed to investigate the allegations. The harder she pursues it, the more she risks antagonizing one of Massachusetts’ most politically powerful Democrats, as well as his allies and supporters across the state. Yet if the investigation doesn’t lead to prosecutions, many will accuse Healey of tanking the case for political reasons.

Still, it’s impossible to forget that Healey has an edge that none of her predecessors ever did: a punching bag in the Oval Office who upstages all competing headlines. Anything that might cause Massachusetts voters to sour on her, it seems, is forgotten as soon as she takes the next swing at Trump.

For all the political hay it’s made, however, is Healey’s campaign against Trump having a real impact? So far it’s been a mixed bag. Most of the actions she’s taken against the administration remain pending in court, while the policies they aim to block proceed. Healey sounds convinced that the actions she opposes are clearly illegal, as well as (in her opinion) bad policy, but she doesn’t seem to be convincing the conservatives who control the White House, Congress, and the Supreme Court. The biggest success of Healey and her fellow Democratic AGs has been the repeated defeat of Trump’s executive order on immigration—the ban on those coming from certain Muslim countries. Yet the Supreme Court recently allowed the latest version of the ban to remain in place while challenges work their way through the courts, a major victory for the White House.

That’s not to say that the big legal actions are moot or frivolous, or serve only a political purpose for the woman bringing them. The pending suits on education, the environment, DACA, and transgender military service could be setting the stage for a series of policy setbacks for Trump in 2018. And more to the point, as Healey tells me, it’s important to fight back against the regressive, ugly impulses that have been oozing out of Washington. “I don’t wake up every day wishing to sue the president of the United States,” she insists. “When you have a president and an administration who are doing things that are basically unconstitutional or illegal, somebody has to be there. If the AGs don’t sue, who else is going to prevent the abuse?”

Which brings us to a final point: As much as Healey’s efforts to frustrate the Trump administration’s every move may seem like her throwing red meat to a liberal base, Trumpism is an attack on many of the ideals and ideas that most residents of the state seem to agree on. Despite some deeply conservative pockets and an affinity for Republican-lite governors who preach an anodyne “pro-business” platform, there isn’t much of an audience for Trump’s policies here. Healey is right when she says that the White House policies she’s fighting would do harm to our citizens and their ideals. Standing up against them might be good politics, but that doesn’t mean that doing so doesn’t also represent the will and values of her constituents. In fact, that it’s good politics is evidence that it is a good use of her powers.

That could help explain why Healey has managed to be an aggressive fighter without becoming saddled with the ominous prosecutorial image that voters often associate with top elected law-enforcement officials—whom they then can’t warm up to when asked to think of them as governor or senator. She might be a skull-cracker, but she’s the people’s skull-cracker. So, whenever she finally earns her nickname in Trump’s tweets, it’ll be well deserved. I just can’t wait to see what it’ll be.