Opposition Party

The Threat Trump Never Saw Coming

As the Democratic Party remains mired in its own existential crisis, the resistance to Donald Trump is being led, in part, by an unlikely group of attorneys general—starting with Maura Healey.
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Maura Healey arriving at a press conference to announce that her office will be challenging Donald Trump’s executive order on immigration on Janary 31, 2017.From The Boston Globe/Getty Images.

The morning after Donald Trump was sworn in on the Capitol steps, Massachusetts Attorney General Maura Healey looked out over a massive crowd of her own. Some 175,000 demonstrators had gathered on the Boston Common to protest the new president, and Healey—flanked by Massachusetts senators Elizabeth Warren and Ed Markey—was prepared to stir their fervor. She vowed to fight the administration on topics ranging from women’s issues to corporate interests, and declared an unequivocal warning to the famously litigious new president. “The message from the people of Massachusetts is: We’ll see you in court,” Healey said.

The Democratic prosecutor got the fight she was looking for faster than she could have possibly fathomed. On January 31, Healey joined attorneys general from three other states to sue the U.S. government after the Trump administration closed America’s borders to refugees and non-U.S. citizens from seven predominantly Muslim countries. The suit, of course, followed days of chaos, as airports around the country descended into disarray. In a matter of hours, hundreds of people, including green-card holders, had been detained, pulled off flights, or separated from their families. The Department of Homeland Security, which was only marginally involved in the drafting and rollout of the plan, scrambled to figure out what the changes meant. Thousands of protesters stormed J.F.K., LAX, Dulles, and other international airports as a small army of lawyers were deployed to arrival terminals to offer pro-bono legal advice to immigrants and families ensnared in Trump’s dragnet.

As Boston’s Logan International Airport became a flash point of the country’s latest culture war, Healey’s office was among the first to get involved. Two days after Trump signed the order, she issued, on a Sunday, a joint statement with 16 other attorneys general condemning the White House directive. Two days later, she joined a federal lawsuit filed by the American Civil Liberties Union, which challenged the E.O. on the grounds that it was a religious test. “The president’s executive order is a threat to our Constitution. Rather than protecting our national security, it stigmatizes those who would lawfully emigrate to our state,” Healey said in in a statement. “The [Trump] administration has embarrassed and endangered our country. On behalf of the Commonwealth, my office is filing intervention papers to challenge the immigration ban and hold this administration accountable for its un-American, discriminatory, and reckless decision-making.”

Healey didn’t mince words when I asked her how she sees her job amid the new reality of the Trump administration. “We need to stand up for the rule of the law,” she said. “And if the administration attempts to carry out unconstitutional campaign promises, we need to be there to take that on.” Indeed, attorneys general are often among the first line of defense against abuses by the federal government, and Healey indicated that if the new administration took steps to curtail environmental or financial regulations, anti-trust and labor laws, or moves forward with a number of the controversial—and in some cases, unconstitutional—policies that Trump pitched on the campaign trail, her office would be prepared to hit President Trump with a fusillade of legal attacks.

Less than a month into office, Healey’s warning is already being tested. The Democratic Party has been rendered largely inert and anemic after a string of disappointing midterm and general elections during the Obama era. In the wake of Trump’s surprising victory, it has appeared somewhat rudderless as it grapples with its own internal Tea Party moment while endeavoring to thwart Republican momentum on Capitol Hill. Into this vacuum, the courts have emerged as ground zero for the Trump resistance—as demonstrated by Thursday’s Ninth Circuit U.S. Court of Appeals ruling. Borne of necessity, attorneys general like Healey and judges like James Robart have emerged as, arguably, the most effective adversaries of Trumpism.

VIDEO: The Long List of Lawsuits Against Donald Trump

Upon entering office, Trump presented A.G.s with a uniquely vexing challenge. On the stump, he offered disaffected American voters a potent combination of xenophobic, populist and “politically incorrect” rhetoric but little in the way of concrete policy or ideological moorings, all of which rendered him a blank slate, of sorts. But a number of potent intimations on his agenda were revealed during his transition, as Trump increasingly surrounded himself with immigration hard-liners, K-street operatives, and .001 percenters. Meanwhile, he stocked his Cabinet with controversial appointees such as Andrew Puzder as secretary of the Department of Labor, Scott Pruitt as head of the Environmental Protection Agency, and Jeff Sessions as United States attorney general. “One thing about Trump is that he is unpredictable, but certainly personnel is policy. He is putting in place people that really are at odds—and in some cases fundamentally at odds—with the purposes of their agencies,” Eric Schneiderman, the New York State Attorney General, whose office also joined the A.C.L.U.’s fight against Trump’s immigration order, told me recently. “These are things that we take as an indication that they are not backing off from some of the extreme positions that they took on the campaign trail.”

In the short time that he has held the Oval Office, Trump has already started to unwind Barack Obama’s legacy. Within three days of taking the oath of office, the new president blocked an Obama administration policy that would have reduced the cost of Federal Housing Agency-backed mortgages for millions of low-income Americans; signed a sweeping (albeit vague) executive order allowing federal agencies to “ease the burden of Obamacare” to the “maximum extent permitted by the law;” withdrew from the Trans-Pacific Partnership; reinstated the “Mexico City Policy,” which bars funding to international nongovernmental organizations that perform or even discuss abortion; and instituted a federal hiring freeze. In addition, as the official White House Web site transitioned from the Obama to the Trump administration, it omitted any mention of “climate change,” and the government pages about the L.G.B.T. community and health care disappeared. Then, of course, Trump capped off his first week in office with the signing of the controversial executive action on immigration.

By Jessica Rinaldi/The Boston Globe/Getty Images.

To some extent, Democratic attorneys general will borrow from the playbook that their conservative counterparts created during the Obama administration. As President Obama combatted an uncompromising Congress on Capitol Hill for much of his time in office, he was simultaneously fighting a protracted battle on another front. Republican attorneys general from states including Arizona, Nevada, Virginia, Texas, Oklahoma, and Florida made suing the federal government something of an avocation over the past eight years, taking the administration to court over a range of issues from health care to labor laws to environmental regulations.

Their Democratic colleagues are now poised to do the same. But unlike Texas attorney general Greg Abbott, who famously declared in 2013, “I go into the office, I sue the federal government, and I go home,” Healey doesn’t seem to relish the thought of taking Trump to court—even if she is prepared to do so. “I certainly don’t wake up every day looking forward to an opportunity to sue a Trump administration or to sue the federal government,” she told me. “I nevertheless will stand at the ready to make sure that we are enforcing the law to protect the interests of Massachusetts and the people that live here.”

Being a voluble, vociferous attorney general, however, isn’t without its benefits. Schneiderman, whose office brought a class-action against Trump University, the president’s now defunct real-estate training company, negotiated a $25 million settlement at the end of last year and is now rumored to be considering a gubernatorial bid in 2018. (Eliot Spitzer followed a similar path a decade ago, before succumbing to scandal.) Healey, the first openly gay attorney general, is herself a rising star among political progressives and has been floated as a potential challenger to Massachusetts governor Charlie Baker. “There are a lot of tools in our constitutional tool box, it is just about having enough state A.G.s with the foresight and the courage to take these fights on,” Schneiderman told me during an interview, before adding, “Maura has proven to be an A.G. that is not gun shy.”

Healey may have been a first-time political candidate when she was elected attorney general in 2014, but she was far from a neophyte. For the seven years prior to her campaign, Healey worked under her predecessor, Martha Coakley, and, while serving as head of the Civil Rights Division, was the architect of the successful challenge to the federal government’s Defense of Marriage Act, which she argued in federal court. Widely seen as the underdog in the election—which Adrienne Kimmell, the executive director of the Barbara Lee Foundation, a group that studies female campaigns, characterized as “a race against the old boys club in a lot of ways”—Healey beat her opponent John Miller in a landslide, securing over 62 percent of the vote. When I asked whether she thought her status as a first-term attorney general hindered her agenda, Healey dismissed the impact. “I don’t have a playbook for this. You’re right, I haven’t been in politics for many years, I haven’t held other offices before, but I am just going on what feels right to me, my experience and my judgement,” she said.

In her short time in office, Healey has pushed an aggressively liberal agenda. She has tackled such issues as student loans and for-profit colleges, workers’ and women’s rights, sexual assault, the opioid epidemic, and was instrumental in getting a transgender public accommodations law passed. But it has been the fierce battles with large lobbies and corporate interests that have amplified her profile and arguably prepared her to take on Trump. “It is very easy for a lot of the big players and a lot of the big corporate interests to have and to hire all the lawyers in the world to advocate for them, to hire lobbyists to spend time in state legislatures and in Congress,” Healey explained. “It is really important that every day real people have somebody out there, looking after them, looking after their families and that is how I see my role.”

Like Schneiderman, Healey has developed a reputation as an activist attorney general. Together, the New York and Massachusetts attorneys general launched a fraud investigation into whether ExxonMobil—whose former C.E.O. Rex Tillerson is Trump’s recently confirmed secretary of state—misled investors about the impact of fossil fuels on the environment. (The lawsuit prompted ExxonMobil to file a series of countersuits against Healey and Schneiderman. In a statement to Vanity Fair, spokesperson Alan Jeffers said, “We are pushing back on the investigations because we feel that the investigations themselves are politically motivated, in bad faith and don’t have any legal merit.”) Healey has also launched a series of broadsides against the Massachusetts gun lobby. In addition to investigating two gun manufacturers over potential safety issues, her office most notably moved to enforce an existing Massachusetts assault weapons ban last July when it closed a loophole that allowed the sale of “copycat” and “duplicate” weapons. The move has drawn the ire of gun-rights advocates and on January 23, the Massachusetts chapter of the National Rifle Association sued Healey and Governor Baker over the assault weapons enforcement. (Jim Wallace, the executive director of the Gun Owners Action League, which brought the suit, said, in a statement to Vanity Fair, that the organization was unable to comment on pending litigation).

Healey’s efforts have drawn the praise of former Arizona Congresswoman Gabrielle Giffords, a powerful advocate for gun control, who was badly injured during a 2011 shooting that killed six people. Giffords e-mailed me that the people of Massachusetts are “lucky” to have Healey, who Giffords said “will always put their safety ahead of the corporate gun lobby, and never stop fighting for them.” In an e-mail, Senator Warren echoed Gifford’s sentiment, characterizing Healey as “a tough, smart fearless woman who knows how to get things done.” She continued: “Powerful interests who think they can push her around still haven’t learned their lesson: Maura isn’t just Massachusetts’s lawyer, she’s the people’s lawyer—and she is not afraid of anyone.” Including, it seems, Donald Trump.

When I asked Healey about criticism that she has overstepped her authority in the pursuit of her progressive agenda, she replied candidly. “I think there are some people that just don’t like what we are doing, that maybe disagree as a matter of policy. That is O.K., they will take their knocks, that’s O.K. There are some people that don’t understand the authority of the office,” she said. “But I know that if we are going to take action and be an office that is about action, we are not going to please everybody all of the time, and that is O.K.”

Healey hastened to position herself as an opposition force to the new Republican administration. But with Democrats busy assigning blame for Clinton’s unexpected loss and the party’s enduring failure to coalesce around a clear objective or message, the role of Healey and other state attorneys general has taken on an unrivaled eminence. “I think that the concept is that the more that the Trump administration pulls back from regulation and enforcing our laws . . . the more you will see, going forward, state attorneys general filling that vacuum,” Doug Gansler, a former Maryland attorney general and former president of the National Associations of Attorneys General, told me. “And Maura Healey will be a leader in doing just that.”