Second of two profiles on the major candidates for governor. See Geoff Diehl’s profile here.
It took a whole nine days as attorney general-elect for Maura Healey to top a list of Massachusetts Democrats’ best hopes for retaking the governor’s office.
After a bagpipe procession and an overflow crowd marked her inauguration in January 2015, one strategist said it felt like the “inauguration of the governor of the Democratic Party.” That March, Governor Charlie Baker quipped that Healey was already “putting her lawn chair in my parking space.”
Healey’s candidacy, it seems, has always been inevitable.
Her face tightens talking about it.
“ ‘That’s what you do: You run for AG, and then you run for governor.’ Personally, I bristled against that for years,” the South End Democrat said in a recent interview. “And, in fact, part of me was, ‘That’s not going to be me.’ ”
Until, of course, it was.
Eight years after she rose from political obscurity, Healey heads into Election Day as close to a foregone conclusion in the race for governor.
During her two terms as top prosecutor, she built a national reputation as the state’s litigator-in-chief against Donald Trump, and an activist attorney general at the forefront of fights against opioid manufacturers, tech companies, and others.
When she finally announced her gubernatorial bid in January, she cleared the Democratic field in five months, piled up donations, and built enormous leads in public polling over her Republican rival, Geoff Diehl. They’ve hardly budged since.
The situation is, in many ways, exactly what many Democrats envisioned for her. The head of the state party, Gus Bickford, privately discussed her as a potential gubernatorial candidate at least three years ago. Steve Grossman, a former candidate for governor himself, recalled urging Healey shortly after she took office in 2015 to embrace a larger portfolio of issues, including economic ones, to avoid being boxed in as simply the state’s chief law enforcement officer.
“I said something like, ‘Maura, I have no idea where you’re going to be in four years, or eight years, or 12 years from now, but it’s not beyond the realm of possibility that you may consider running for governor,’ ” Grossman said. “It wasn’t a big leap for me.”
Healey insists that, for her for many years, it was. And should she beat Diehl on Tuesday, those who know her well say her victory would be less a confirmation of a well-plotted path than an extension of an unlikely trajectory from political novice to the summit of state politics.
“Politics is a means to the end,” said Tom Reilly, a former attorney general and one of four since 1990 to unsuccessfully seek the governor’s office. “She has a chance [at something] that none of us were able to do. She wants to be governor for the job, not the position.”
Before her first campaign as attorney general, Healey had never worked as a campaign staffer nor frequented local Democratic town committee gatherings, grass-roots proving grounds for the politically ambitious.
She had worked for years in private practice, rising to the level of junior partner at a firm now known as WilmerHale, before shifting to the attorney general’s office under Martha Coakley in early 2007. Her father, Jerome, had died from colon cancer just months earlier, and Healey, long drawn to public work, emerged from the grief with what she described as a “life-is-short” perspective.
She quickly built a reputation in legal circles as an earnest and creative civil rights attorney. She helped bring a first-in-the-nation civil rights claim against a subprime mortgage lender, and led the first successful challenge to the Defense of Marriage Act, the federal law that denied rights to same-sex couples — a case Healey described as life-changing and that remains one of her best-known legal victories.
After antiabortion activists filed a 2008 challenge to a law banning them from within 35 feet of clinics, Healey traveled to several clinics to see their so-called buffer zones first hand, said Jesse Mermell, then the vice president for external affairs for Planned Parenthood League.
On one site visit with Healey in Springfield, Mermell recalled turning around to find Healey climbing through waist-high bushes to fish out pamphlets that protesters had been able to leave inside the boundary. When they visited a Boston clinic, she asked to go on the roof. Mermell said she wanted a better vantage point to take photos.
“I thought, ‘Holy [expletive] she means business,’ ” Mermell recalled. (The case ultimately landed in the Supreme Court, which overturned the law.)
Outside work, Healey spent four years taking meeting minutes for a genealogical society she and her family have long belonged to.
“She wasn’t just a political person,” said David Friedman, a former top deputy under Coakley who helped recruit Healey to the office. When Healey told him 6½ years later that she wanted to run to lead it, he said he was thrilled.
“And also surprised,” Friedman said. “ ‘Oh, you want to run for office?’ I didn’t necessarily see that coming.”
Massachusetts politics didn’t either, for the most part. When Healey emerged victorious in the 2014 Democratic primary, she not only overcame Warren Tolman, a former state senator, but the tide of support he got from labor groups and party stalwarts, from then-Governor Deval Patrick and then-Boston Mayor Martin J. Walsh to four former attorneys general, Reilly included.
“I was wrong. I was very wrong,” Reilly said. “She was the best person for that job. I should have said it.”
But as Healey’s profile quickly expanded, so did the scrutiny of her decisions.
She targeted corporate powers, particularly in the fossil fuel industry, drawing complaints from ExxonMobil that her suit claiming it knew its products were contributing to dangerous climate change was politically motivated. (The state Supreme Judicial Court rejected the company’s argument.)
She’s been hailed as a state-level bulwark against an array of Trump administration policies, suing the federal government nearly 100 times and most times, successfully. But Republicans charge that her focus on Trump was a cynical bid to boost her political profile, and that she did so at the expense of other duties. Healey, for example, has never charged a Democratic elected official with corruption during a span when federal officials in Massachusetts have won convictions against at least three, and charged a fourth.
“Since the AG’s office has limited resources, for every politically motivated lawsuit that was filed, for example, that could have meant one more drug dealer who went free, one more public official who got away with corrupt acts,” said Dan Shores, a lawyer who ran for the GOP nomination for attorney general in 2018.
Healey and her supporters dispute that. For one, many of Trump’s policies, either to roll back environmental regulations or ban travel from several Muslim-majority countries, were true threats that demanded a response, they contend.
“I don’t know that she sought out politics,” said Representative Dylan Fernandes, a Falmouth Democrat who was Healey’s first campaign driver and later worked in the attorney general’s office. “That was an era where politics was thrust upon her and the AG’s office.”
Healey herself pushes back against the idea that higher political ambitions drove her decision-making — that “she did this to set herself up for something else.” The governor’s office, she contends, was not on her radar.
“That’s the thing. It was never a foregone conclusion that I was going to run for governor. It wasn’t,” Healey said. She also struggles to pinpoint exactly when she did consider it. “I think probably last year sometime.”
Few people claim to know for sure. As her political star rose, Healey maintained a tight political circle, leaning on her younger sister, Tara, or Corey Welford, a longtime adviser who also worked for Coakley, among a handful of others. Many supporters recount serving as sounding boards for her, particularly before her 2014 run, but few say they’ve actually been in the room when decisions are made.
“Maura’s a very private person,” said Grossman, the former state treasurer. “Her decisions about how she was going to build her career were decisions that were developed over a long period of time.”
She also hasn’t shied from wielding her political clout. She’s littered the ballot this year with endorsements, many reflecting a level of political loyalty to past supporters. She took the unusual step of not only publicly supporting former Boston city councilor Andrea Campbell in the contested primary for attorney general but also throwing the weight of her political operation behind her in the race’s closing weeks. In doing so, Healey altered the primary and perhaps the result. Campbell won handily and is polling well ahead of Jay McMahon, her Republican opponent.
It also eventually put Healey at direct odds with other political leaders, including Boston Mayor Michelle Wu, who backed Campbell’s opponent, Shannon Liss-Riordan. Wu’s decision reportedly angered Healey, who, too, was miffed that Wu didn’t endorse her until weeks after Healey’s final primary rival, Sonia Chang-Díaz, dropped out of the race.
The two both publicly said it wouldn’t affect their working relationship. But it left some party insiders wondering what it portends for Healey’s expected role as de facto party leader, should she win the governor’s office.
“She’s a kingmaker,” one Democratic operative said. “Now that she has this power, I think she’s aware that she can use it.”
Healey expresses discomfort with publicly mapping too far in front of her. She described her eventual embrace of running as an evolution, and said she does not harbor further political designs. Asked what her political ambition is, she quickly answered: “None.”
Jocelyn Jones, a longtime friend and former assistant attorney general, said she “never thought about [Healey] being governor,” nor did Healey openly aspire to it before ultimately deciding to run.
“Personally, I have thought she should run for president,” Jones said.
Healey laughed at the suggestion. But it also may be an unavoidable one given that, before Baker, four of the last five governors elected in Massachusetts later ran for president.
“No grand plan or scheme for how this unfolds,” Healey said.
Indeed, her decision to run for governor may have turned in, of all places, a kitchen in Essex.
During a visit to her brother Terence’s home last year, Healey asked his youngest daughter, Cece, whether she thought she should run.
Cece, Terence said, quickly asked if she would be the first woman to be elected. She would, Maura responded. (While Jane Swift served as acting governor 20 years ago, Massachusetts has never elected a female governor.)
“Then Cece — without a pause — said, ‘You have to do it, right?’ ” Terence said, laughing at the memory. “That sealed it. That exchange, I’ll never forget that. A light clicked in Maura’s eyes.”
“Or,” he quickly added, “maybe I imagined that.”
Matt Stout can be reached at firstname.lastname@example.org. Follow him on Twitter @mattpstout.