Zephyr Teachout launched her campaign for New York state attorney general outside of Trump Tower in JuneMark Lennihan / AP

NEW YORK—Technically, the headquarters of Zephyr Teachout’s campaign to be New York’s next attorney general are in a former doctor’s office in Spanish Harlem, a drab ground-floor storefront where the Fordham University law professor plots electoral strategy, lawsuits, and prosecutions.

But the heart of her bid—metaphorically, politically, substantively—is about three miles south, on the sidewalk across from Trump Tower. It is there where Teachout launched her campaign in June, and it is the president’s business empire that she wants to investigate, prosecute, and even dissolve if the voters of New York make her the state’s chief law-enforcement officer this fall.

“Donald Trump’s businesses are here,” Teachout explained on a recent Tuesday morning. “What the New York attorney general can do, and as attorney general I’ll make a priority, is investigating those businesses. That power extends to, in the case of extreme illegality, dissolving businesses.”

Teachout, 46, was sitting in an exam room that was empty except for a metal desk and a pair of chairs. The medical business that had previously occupied the office had apparently vacated the suite so quickly, she explained, that one of her aides found a lab coat hanging on a door when they moved in.

The attorney general’s race had begun just as hastily two months earlier. Until this spring, the campaign was expected to be a sleepy reelection for Eric Schneiderman, the 63-year-old Democrat in his second term who had made a national name for himself going after Wall Street banks, payday lenders, fantasy-sports websites, and, of late, Donald Trump and his administration. But Schneiderman abruptly resigned on the evening of May 7, just three hours after The New Yorker reported that four women had accused him of physical assault. It was perhaps the swiftest political downfall in an era—and a state—that has seen plenty of them. And it immediately set off a spirited primary campaign for a statewide post that has served as a launching pad to the governor’s mansion for two of its most recent occupants, Eliot Spitzer and Andrew Cuomo.

Letitia James, the New York City public advocate, quickly threw her name in and earned endorsements from Cuomo and a bevy of powerful Democratic elected officials, unions, and advocacy groups. Teachout, who challenged Cuomo for governor in 2014 and was serving as the campaign treasurer for Cynthia Nixon’s 2018 gubernatorial bid, soon followed, as did Leecia Eve, a former aide to Cuomo and Hillary Clinton. Representative Sean Patrick Maloney, a House Democrat in his third term, joined the race in June, waving aside concerns that his victory could endanger a competitive congressional district for Democrats. The Republican nominee is the Manhattan attorney Keith Wofford, but whichever Democrat wins the party’s September 13 primary will be heavily favored in November.

The Democrats are all, to one degree or another, running on the explicit promise of taking on Trump and protecting New Yorkers from his administration’s conservative policies. They’re seizing on the unexpected opening of a plum elected perch with a big national spotlight, and on the desire of progressive voters—already energized for the midterm congressional elections—to fight the president in whatever way they can. But the attorney general’s race is also caught up in a turbulent New York political moment, one that pits veterans of the state’s Democratic establishment against insurgents trying to push the party to the left.

Teachout has won the endorsement of New York’s newest political star, Alexandria Ocasio-Cortez, the 28-year-old who toppled long-serving Representative Joseph Crowley in a June congressional primary. James, a Brooklyn native who rose to prominence waging progressive fights against power brokers in City Hall, has cast her lot with a governor who appears well positioned to fend off Nixon’s challenge to his reelection to a third term. Maloney is leaning on his experience as a former aide to a president and two New York governors, as well as his success winning, and holding, a congressional seat that once belonged to Republicans.

Both James and Maloney have deeper ties to the state and its entrenched Democratic machine, but Teachout is the candidate of the activist left. And if an outsider’s energy and message can carry the day in New York—not merely in a single congressional district, but in a statewide election—this summer’s wide-open attorney general’s race may be where it happens.

For decades, the New York attorney general’s office had been little more than a glorified consumer-protection bureau, targeting shady landlords and businesses for abusive practices. In the early 2000s, the hard-charging Spitzer raised the profile of the office—and himself—by going aggressively after New York City’s banking industry. He earned himself the moniker the “Sheriff of Wall Street” by forcing major financial firms to shell out billions in fines for defrauding investors. When Spitzer became governor in 2007, Cuomo used the office to resurrect his career after a failed gubernatorial bid in 2002.

Trump’s election in 2016 made national figures out of a group of state attorneys general from blue states who were determined to fight the president and elevate themselves in the process. They became newfound federalists, following a path set by their conservative counterparts during the Barack Obama years who had positioned themselves and their offices as bulwarks against policy emanating from the White House. Joining Xavier Becerra in California, Maura Healey in Massachusetts, Lisa Madigan in Illinois, and others, Schneiderman signed onto lawsuits targeting the Trump administration over immigration, LGBTQ rights, its efforts to undermine the Affordable Care Act, and more.

Schneiderman had already made an enemy of Trump by suing Trump University in 2013, a case that eventually led to a $25 million settlement. And it was his two-year investigation into the Trump Foundation that led his interim successor, Barbara Underwood, to sue the charity in June. The suit alleges a wide array of state and federal crimes, and it seeks to dissolve the foundation and bar Trump and the board of directors from serving on other nonprofit boards in the state.

It is that role—Trump’s Javert in New York—that James, Teachout, Maloney, and Eve are all vying to fill. And none is vowing to pursue the president with quite as much zeal as Teachout. Continuing the lawsuit against his foundation would be only the beginning, she told me. If elected, she would investigate and likely sue the Trump Organization as well, and she would add New York to a lawsuit filed against the president in Maryland and Washington, D.C., that seeks to force him to divest from his businesses. Teachout has already sued Trump as president, joining and advising a case brought against him soon after he took office alleging that he violated the Constitution’s emoluments clause. A federal judge dismissed that suit in December, but the case brought by the states is proceeding.

For weeks earlier this summer, Teachout had called on Cuomo to allow Underwood to launch a criminal investigation—as opposed to just a civil probe—into the Trump Foundation by making a referral required under state law. In a minor victory for her campaign, the governor said he would do so last month.

Teachout told me she would prepare the attorney general’s office to step in if Trump fired Robert Mueller or pardoned associates now under investigation by the special counsel or federal prosecutors in the U.S. attorney’s office in Manhattan. While the president’s pardon power under federal law is virtually unlimited, it does not apply to violations of state law.

Teachout also sees the post as a prosecutor of last resort against Trump himself. When I asked her if she would seek to indict the president for crimes related to his businesses—something Mueller might not even try to do in the collusion and obstruction probe—she told me she wanted to research the question before responding. She called back a few days later. “I want to be super clear,” she told me, “that I am ready to indict if the president broke the law and it looks like he won’t be held accountable.”

Whether the New York attorney general could actually have the impact Teachout is promising is unclear. State laws protecting defendants against double-jeopardy prosecutions could limit her ability to bring cases against pardoned Trump associates, and even she acknowledges that the power of a state attorney general to indict—and prosecute—a sitting president is untested. But she’s betting that in a Democratic primary battle, merely raising the possibility makes for good politics anyway.

This is Teachout’s third campaign for office in New York in the past five years; she garnered a better-than-expected 33 percent against Cuomo in 2014, and lost a congressional race to the Republican John Faso in 2016. But of the three, this may be the job that suits her the best. Teachout began her career as a death-penalty lawyer in North Carolina and now specializes in constitutional and anti-corruption law at Fordham. She wrote a history of corruption in American politics while running for governor against Cuomo, and she previously served as the executive director of the Sunlight Foundation, which advocates for transparency in government. Early last year, she helped the good-government group Citizens for Responsibility and Ethics in Washington file a lawsuit against Trump in federal court that accuses him of violating the Constitution’s emoluments clause by profiting off his businesses while in office.

“I have a deep expertise in this area of law that is now painfully relevant,” Teachout said.

She has continued to go after Cuomo as well, highlighting the convictions of his top aides on corruption charges, and casting herself as the most independent of the Democrats running for attorney general and the candidate best positioned to help clean up Albany’s long history of graft. Teachout has forsworn donations from corporations, arguing that that will allow her to aggressively go after abuses by major real-estate firms and landlords, health-care companies, polluters, and the other traditional targets of the attorney general’s office.

Her platform isn’t all about Trump. With a nod to Schneiderman’s demise, she has pledged to investigate allegations of sexual misconduct in state government. Ending mass incarceration in New York is another focus. And she has gone beyond Ocasio-Cortez’s early call to “abolish” Immigration and Customs Enforcement by saying she would “prosecute ICE for their criminal acts.” (When the acting ICE director responded to Teachout’s vow on Fox News, her campaign rejoiced.)

But much of Teachout’s agenda—investigating the president’s businesses, corruption in state government, and major New York City real-estate firms—connects back at Trump Tower. “It’s actually related,” she told me. “Because Donald Trump’s criminality comes out of New York City real estate. New York State’s corruption comes out of New York City real estate. The unaffordability of living in New York City come[s] out of New York City real estate.”

Teachout stands a much better chance of becoming attorney general than she did of becoming governor four years ago. But despite her higher profile and appeal among progressive activists, she is not the favorite in the Democratic primary. If there’s a frontrunner, it is Tish James, the 59-year-old former Brooklyn councilwoman who since 2014 has served as New York City’s public advocate. The elected post is akin to an ombudsman for the city; it comes with little actual power, but its occupants have used the perch as a soapbox to spotlight issues, propose laws, and raise their profiles on the way to higher office.

Until the evening of May 7, James’s next run for office was likely to be a 2021 bid to become the first woman—and only the second African American—to lead the nation’s largest city. But then The New Yorker story about Schneiderman published online. She told me she was sitting down to appetizers at a diner that night when she learned that Cuomo had called on the attorney general to resign. By dessert, Schneiderman was out.

“All of a sudden, my phone went crazy. It just blew up,” James recalled. By the next morning, she was running for attorney general.

Before her election to the City Council in 2003, James had worked as a lawyer for years—first as a public defender for the Legal Aid Society, then for the state legislature and Governor Mario Cuomo’s administration, and later as a high-ranking official in the attorney general’s office under Spitzer. She began our interview by listing the many areas of overlap between her work as public advocate and what she’d continue to do, with more authority, as attorney general: policing Wall Street, targeting abusive landlords and predatory lending, defending immigrants in New York against the Trump administration’s crackdown. “The attorney general has to be an activist, has to be on ground, has to have a grassroots background,” James told me.

Politically, it’d be hard for an opponent to get to James’s left: She was the first candidate to win an election in New York on the liberal Working Families Party line, and she waged fights at City Hall on behalf of poor tenants, victims of domestic and gun violence, and people of color disproportionately affected by the police department’s “stop-and-frisk” policy—those who, in her words, had been “invisible for far too long.”

It is that record of activism, and that connection with voters in New York City, that James is leaning on to distinguish herself from Teachout, who grew up in rural Vermont, practiced law in North Carolina, and has never held public office. James’s allies frequently note that Teachout is not admitted to the New York bar. (Teachout told me that that will be fixed by the election.)

“Zephyr has never represented anyone but herself,” Harlem Assemblywoman Inez Dickens told me. “How she can represent an entire state like New York—ethnically, racially—it’s impossible. She’s never done it before.” (In response to Dickens, Teachout cited her early career work on death-penalty cases: “I represented the most hated people in society,” she told me.)

James has said she would continue the lawsuit against the Trump Foundation and wants the state legislature to give the attorney general power to bring criminal prosecutions without the governor’s sign-off. But she has focused more broadly on the Trump administration’s policies—on women’s rights, immigration, gun violence, and the environment—than on the president himself. And she has stressed her relationships with other powerful Democrats in New York to argue that a concerted effort by the entire state government to push back on the White House would be more effective than the attorney general doing so by herself.

James is benefitting from the support of Cuomo, the Democratic state committee, and several powerful unions, all of which are helping her raise money and could make the difference in what is expected to be a low-turnout primary on September 13. But at a moment when progressive voters are turning away from insiders, that establishment backing could also be a burden.

“I definitely think she opened the door for Zephyr to claim that outsider mantle,” said Christina Greer, a political-science professor at Fordham who is neutral in the race. James is also supporting Cuomo’s reelection against the challenge from Nixon and has repeatedly defended the governor’s record and rhetoric against criticism from the left. “Obviously this is a strategic choice that she is well within her rights to make,” Greer said. “But some people see it as abandoning her progressivism.”

James dismissed the suggestion she had compromised her independence. “I’m not going to change how I view the world, or how I feel, or my passion simply because this governor decided to support me,” she told me. “I am not going to surrender my progressive credentials to anyone. I refuse. I will always be a champion for change and for progressive causes in the city and in the state. I will not back down from any fight.” She shifted her focus to the Republican in the White House: “What I am is a street fighter, and that’s the only thing that Donald Trump respects and understands.”

Teachout called on her opponents to join her in rejecting donations from the corporations they would be overseeing. But James told me she would not “unilaterally disarm,” citing the long-documented challenges that African American women candidates have had in raising money. “I’m not prepared to unilaterally disarm because I will be disadvantaged,” she said, calling for campaign-finance reform that would put all candidates on equal footing. In the first filing period of the campaign, James raised twice as much money as Teachout, $1.1 million to $550,000.

James is expected to be dominant in New York City, where minority voters make up the bulk of the Democratic primary electorate. She is not well known upstate, and that’s where Teachout surprised Cuomo with a strong showing in 2014.

Two early polls of the race show James in the lead with around one-quarter of the Democratic vote, and with Maloney and Teachout bunched close together about 10 points behind. Eve lags further back in fourth. But with more than four in 10 respondents in both polls undecided, the race remains wide open.

The wild card is Maloney, who has drawn criticism from Democrats—and a lawsuit from Republicans—for running simultaneously for attorney general and for reelection to his House seat in a competitive district north of New York City. He says he would withdraw from the congressional race if he wins the state primary in September, which would force Democrats to field another candidate less than two months before the election. He is sitting on more than $3 million in campaign funds in his House account, but there are questions about whether he can use them for the attorney general’s race. So far, he has done little campaigning compared with James and Teachout.

“Democrats need to be as good at winning as we are at worrying,” he told me in response to those concerns, insisting that he is “100 percent committed” to keeping his congressional seat in Democratic hands in a year when the House majority is up for grabs.

In an interview, Maloney accused James of compromising her independence by accepting fundraising help from Cuomo and suggested they were running as a ticket rather than for two separately elected posts. “When a governor pays for your campaign, that’s unprecedented,” he said, referring to a fundraiser Cuomo held for James. “We have never seen a governor of New York pick up an attorney-general campaign and put it on his shoulders before. How in the hell are you going to be independent of the governor and tell him you’re investigating the Buffalo Billion when he’s paying your bills, when he is raising money, really all of the money you’re raising for attorney general?” Maloney added, in a reference to an upstate economic-development project that has become a corruption scandal implicating Cuomo appointees.

As for Teachout, Maloney said he was concerned about “loose rhetoric” being thrown around that he implied was unprofessional and unethical. “I am going to approach this job like a professional attorney,” he told me, “and I am going to have a mature and responsible approach to wielding the power of this office, because if it’s just about headlines or advancing your career, I think that’s an unethical approach.” In a statement, Teachout responded: “I will not apologize for calling out clear examples of lawlessness by the Trump administration or the Trump Organization,” she said. “If the congressman has a particular legal strategy he disagrees with he should name it.”

Maloney cited his experience at major law firms, as a senior White House staffer, and as a top aide to New York Governors Spitzer and David Paterson, along with his record as “the only guy in this race who’s actually beat Republicans in tough races.”

Maloney is also the only guy in the Democratic race. While the election of James, Teachout, or the lesser-known Eve would mark a step forward for women in New York, Maloney is bidding to become the first openly gay person elected to statewide office. But surrogates for both James and Teachout have treated his delayed entry into the race against three qualified women as an affront, and the James spokeswoman Delaney Kempner characterized his criticism of her boss’s independence as sexist. “For him to assign credit to Governor Cuomo instead of to Letitia James is the height of misogyny and a clear example of why more women than ever are running for public office this year,” Kempner said.

If there’s a meaningful distinction in approach between Teachout, James, and Maloney, it’s not in whether they’d go after Trump, but how. James and Maloney place more emphasis on protecting New York from administration policies. They promise to file or continue lawsuits against federal action—or inaction—in areas like immigration, the environment, gay rights, and consumer fraud. “There’s a set of issues that relate to Donald Trump, but there are a much broader and equally important set of issues that relate to the Trump administration,” Maloney told me. “And I’m concerned about both.” James said she would also pursue Trump’s businesses, but she noted that in criminal prosecution, the powers of the state attorney general are limited. “You can go after him personally, but we should also go after his policies,” she told me.

Implicit in their priorities is a critique of Teachout’s, a suggestion that her laser-like focus on the president’s business empire could detract from the legal fight against policies that have a more direct impact on the lives of New Yorkers. To Teachout, they are all of a piece. She is running as the anti-corruption crusader who sees Trump’s tenure as “a historic crisis”—one that the New York attorney general’s office, despite its relatively small size and limited legal reach, is uniquely positioned to address. “It has never been more important,” she said.

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