Where do you want to fly?

One pale evening in January, Karl Racine was addressing a community auditorium and rapidly losing his grip on the room. Racine was roosted behind a lectern, the 20 attendees mostly slouched in metal chairs and half-zipped winter coats. Only two weeks earlier, he had begun his second term as DC’s attorney general—an elected position that, five years ago, was new on the ballot. Now he found himself mired in a familiar dilemma: trying to explain exactly who the hell he was.

Twenty minutes into his remarks, Racine was still parsing the complex jurisdictions of his office: The AG is the District’s chief legal officer but also shares a criminal caseload with the US Attorney’s Office—part lawyer for the mayor, part public prosecutor. The gazes of the attendees fell to their smartphones.

Then, abruptly, Racine let rip. Did anyone happen to know that the AG’s office has sued or supported legal efforts against the Trump administration, all told, 16 times? The phones plunged. “We’ve brought a case together against Donald Trump regarding the emoluments clause.” Every face was now fixed on the six-foot former point guard. “We allege that the President is profiting from his office,” Racine explained, “in a manner that is completely and totally unprecedented.”

The move has become something of a favorite parlor trick. “You saw that?” Racine asks me later. “Everybody’s like, What?!”

It also captures his grander ambitions in miniature. Not very long ago, Racine was a public official with little name recognition managing a black sheep of an office. Then Donald Trump won the White House, at approximately the same moment his hotel opened just down the street. Now Racine may soon become known to Americans as the guy who sued Trump, became one of the first people to thumb through his tax returns, and, it stands to reason, altered the course of the 45th presidency.

The emoluments suit, in which a pivotal appeals-court ruling is expected this spring, alleges that Trump’s DC hotel and other holdings violate the Constitution’s little-known—and previously untested—anti-corruption provision. “It’s historic,” says Brian Frosh, the attorney general of Maryland and Racine’s co-counsel in the suit. “Nobody’s ever sued anyone, let alone the President, over the emoluments clause.”

The case is notable not merely for its legal novelty, though. Several scholars believe that, while the special counsel’s Russia probe looms like a thundering warship, Racine’s lawsuit may be the silent iceberg that delivers a fateful rupture to the Trump presidency.

Amid all this, Racine has worked up a flurry of other high-profile causes, too. In December, he became the first prosecutor in the country to sue Facebook over the tech behemoth’s handling of private data. And within the past year, his office has led a nationwide coalition challenging the administration’s immigration policies—including the denial of asylum seekers and the legality of sanctuary cities. In one ongoing case, Racine—an immigrant who came to America in 1965—has sued ICE himself.

In less than five years, Racine has transformed a demure agency that defended the city from nuisance suits into one of the most prolific attorney-general offices in the country. “DC has always had a problem of not being treated with the same kind of seriousness nationally that it deserves,” says James Forman Jr., a professor at Yale Law School who teaches criminal law. “Racine, I think, is changing that. He’s taken what’s a new office, in essence, and become a player on the national stage.”

For a city that voted overwhelmingly against the President and must endure living in his shadow, it would be the sweetest kind of cosmic justice to see him taken down a notch by Karl Racine—America’s only immigrant attorney general, at that.

Yet whatever the outcome, these cases have already helped Racine assemble an argument for a larger cause. Several DC politicians and outside lawyers say the District AG’s office now rivals that of any state, and that Racine has elevated the case for DC statehood, under the precept of a simple theory: If you want to become a state, sue like one.

“There really are no more arguments left for why we shouldn’t have autonomy,” says Elizabeth Wilkins, a former Supreme Court clerk who’s now senior counsel for policy in Racine’s office. “We look like a grownup now.”

When Donald Trump, a year into his presidency, smeared refugees fleeing “shithole countries”—“Why do we need more Haitians?” he reportedly asked aides—Racine took special offense.

Racine was born in Haiti in 1962, shortly before his parents fled the country’s blood-soaked Duvalier regime. His father, the mayor of a small town, was in obvious danger—months earlier, a cousin had been rounded up and shot to death. His mother, a linguist, came to study at Howard and Georgetown. Racine and his elder sister were left behind, reuniting with their parents in America three years later. His mother, Racine says, “was not going to raise her kids in a country where we would have to choose either to remain silent or put our lives at risk.”

He pauses, then smiles: “That’s ‘chain migration,’ as Trump would say.”

Racine recounts the family history one afternoon in his Judiciary Square office, the clock tower of the Trump hotel visible from his corner-suite windows. As a child, he spent weekends with his mother and sister in Georgetown University’s library, whispering in Haitian Creole or French, while his father worked in retail, starting as a security guard at Sears. The family lived in Chevy Chase DC. “I knew I was an immigrant,” Racine says. “I didn’t speak English. I remember going to school and feeling like I was literally placed on another planet.”

At 56, Racine is the severe kind of good-looking: His impeccably kept, white-fringed hair encases two raptor eyes that turn up cheerfully at the corners. He has the linguistic tendencies of an appellate lawyer; in casual company, he drops words like “wherein” and “monies.” But silence is his most pronounced mannerism—the stealthy bearing of a litigator lying in wait just to tell you, when you’re all finished, how you forgot to consider Rule 11. With his permanently smiling eyes, the effect can be unsettling, like a Bond villain delighted to realize you’re seated directly over a trap door. He never, ever interrupts.

By the time he became a citizen in 1992, his parents had instilled what his sister, Mika, calls a bicultural and global perspective: There were the years of Sunday gatherings that the Racines hosted for dozens of Haitians, their living room sweet with the scent of onion bouillon and roasting pintade. And year after year, the family went back to Port-au-Prince, a pilgrimage Racine has continued all his life.

Racine was born in Haiti; his parents emigrated so his mother could study at Georgetown. The family had a bicultural life, speaking French and Creole at home in Northwest DC. Racine (far right in both pictures on the left) became a US citizen in 1992, taking his oath at the DC courthouse at the start of his law career.

Sports became his American equalizer. He played basketball in several leagues around the District, then for St. John’s College High School in Northwest DC, and later for the University of Pennsylvania, where he once hit the game-winning free throw against Princeton after being fouled by Craig Robinson, brother of future First Lady Michelle Obama. (This is one episode Racine holds forth on in garrulous detail: “Coach Weinhauer is like, ‘Get in the game!’ Oh, shit . . .” he says. “I was f—ing exhausted.”)

Politics yielded little interest—until law school at the University of Virginia, where he took immigration law. On the weekends, he began driving into the countryside to work at a pro bono legal clinic for migrant farmworkers. “The only people who did that were people who were ‘fighting the power,’ if you will,” he says. “That was my introduction to legal activism.”

For the next 20 years, Racine dashed through the ranks of Washington’s legal elite. “Karl stood out,” says one early mentor, DC District Court judge Amy Berman Jackson, who has been presiding over a number of the cases in the Russia probe. Jackson encouraged Racine, then in his late twenties, to become a US Attorney. Instead, he chose the far less glamorous DC public defender’s office, where he developed a reputation for representing juveniles. He worked in the Office of White House Counsel in the ’90s, representing President Clinton during the Lewinsky era. In 2006, he was named managing partner of Venable, the first black person in the country to helm a law firm of that size.

Back then, DC had not yet elected an attorney general. Instead, the District employed what it called “corporation counsel,” a municipal legal team whose primary duties were to defend the mayor and advise the city’s agencies. In 2010, DC voters approved a ballot measure to establish the first elected AG’s office by 2014, and when the time came, Racine left private practice to run for it. “I just was shocked,” his sister says, describing him as a “quiet, reserved guy.”

Racine had to build a modern AG office in many ways from square one. One of the first priorities was a consumer-protection division, which he used to investigate companies like Johnson & Johnson for allegedly misleading District consumers. The office’s public-advocacy division, among other things, pursues cases of economic justice, such as wage theft—only one of a handful of AG offices in the country to do so.

For many, it would be cosmic justice to see Trump taken down a peg by America’s only immigrant attorney general.

Meanwhile, on the criminal side, Racine quietly established the District as a leader in criminal-justice reform. The AG is responsible for prosecuting nearly all of the city’s juvenile offenders. Since 2015, Racine’s office has quintupled the number of juveniles it has diverted from prosecution into an alternative rehabilitation program. Racine also oversees the only in-house restorative-justice division in the country, mediating disputes between parties instead of prosecuting them—an idea that’s gaining currency as a way to break the cycle of the so-called school-to-prison pipeline.

“Karl was sort of like the first line to hit the beach, and not the tidal wave that came after him,” says Miriam Krinsky, a prominent advocate for criminal-justice reform, referring to the reformers who have subsequently become top prosecutors in Philadelphia and Chicago. “He really is the gold standard.”

The office might have remained a little-noticed landmark on the mental map of locals. Then the Democrats lost the White House and Racine responded in kind.

On Election Night, he left a watch party feeling physically sick. Several months later, during a gathering of AGs at a DC hotel, Racine was pulled into a meeting with Laurence Tribe, a constitutional-law professor at Harvard, and Norm Eisen, the prominent Washington ethics lawyer who was recently named special oversight counsel to the House judiciary committee. The unexpected topic: the myriad ways Trump was violating the Constitution’s emoluments clause—a flashy legal argument that sounded exotic even to the assembled crowd. “I must have slept through emoluments day at law school,” says Frosh, the Maryland AG. “None of us knew what that was.”

Ever since Louis XVI presented Ambassador Benjamin Franklin with a snuff box full of diamonds, the country’s founders were obsessed with how to insulate public servants from such enticements. The passages on emoluments—an archaic term for tributes or favors—were partly the answer. Now Racine, Frosh, and a dozen or so other AGs listened as Eisen and Tribe described Trump’s financial entanglements with foreign banks and properties around the world—a reported $2 billion of assets in all and a potentially irresistible magnet for governments that might wish to curry favor with his administration.

Eisen may have had another reason to be there: His watchdog group, Citizens for Responsibility and Ethics in Washington (CREW), had already brought an emoluments suit against Trump in New York. It was later thrown out (though is now on appeal). The problem, as lawyers knew from the beginning, was who had standing to sue. “We realized,” says Deepak Gupta, supporting counsel in Racine’s case, “that it would really make a huge difference if we could get a state—an attorney general.”

Talk to people in and around Racine’s office and you get the sense there’s an endgame to his high-profile lawsuits: statehood for DC.

With Trump’s vast holdings, a suit could be brought almost anywhere in the country. But a single property stood out among the rest: 1100 Pennsylvania Avenue, the new Trump International Hotel, an easy mark for any diplomat, business, or lobbyist aiming to please the President. Plus, the next-door neighbor of Maryland could prove the emoluments clause’s inverse—that other states were suffering from DC’s gain. As Eisen puts it, “They’re the perfect jurisdictions for this case.” (Neither Trump’s lawyers nor the Justice Department would comment. Eisen spoke to Washingtonian shortly before the House committee hired him.)

In March 2017, Eisen walked Racine and Frosh through the ways in which the lawsuit might be won. Frosh felt readier to commit. But Racine was apprehensive: He wanted to be convinced they had “not just a good-faith argument but a winning argument,” he says. “We couldn’t afford to go forward with a case for simple reasons of publicity.” AGs contend with limited resources; every failed lawsuit here is a malfeasant corporation that goes unsanctioned there, and the work of an AG is funded at taxpayer expense. There was also a chance of reputational damage to a new office like Racine’s, along with another potential risk: “I think the possibility was not lost on anyone that taking this step might mean earning the enmity of Trump and his allies,” says Gupta—meaning “possible retaliation in some form.”

At their final go-ahead meeting, “Racine cross-examined me like Perry Mason,” Eisen says, and “for close to two hours.” DC and Maryland proceeded to file the suit together in June 2017. By then, their material fact-finding was aided by news reports of possible influence-seeking: the Kuwaiti ambassador moving his independence celebration to the Trump hotel, for instance, or lobbyists for the Saudi government booking $270,000 worth of stays at the hotel starting in December 2016.

“The possibility was not lost on anyone that this might mean earning the enmity of Trump and retaliation in some form.”

Twenty months later, the emoluments case has hit a major crossroads. District Court judge Peter Messitte handed down rulings on the lawsuit’s central theory: The emoluments clause could be applied to a sitting President’s business interests. The suit would go forward. Racine and Frosh, in turn, subpoenaed nearly 40 entities, including Trump businesses and federal agencies, for thousands of pages of tax documents that would likely show every diplomat, lobbyist, and politician who has given money to the President’s companies. The Trump administration, in response, requested an emergency appeal. Should Racine and Frosh succeed at quashing the appeal, Eisen says, boxes of the President’s financial records—presumably sitting in a basement somewhere—would be turned over.

If the case proceeds to trial, that could mean some or much of the documents and testimony would become public—a new political albatross for Trump in the year leading up to 2020. Constitutional scholar Noah Feldman, at Harvard Law School, has written that proof of the President’s profiteering from his office would provide “the most clear-cut” legal basis for “constitutionally grounded articles of impeachment against Donald Trump.”

Several people involved in the case, meanwhile, describe Judge Messitte’s decision to approve their core legal argument as a coup in itself—and they cite recruiting Racine as the turning point. “In a lot of ways,” says Gupta, “we already have succeeded.”

Had they known Racine and Frosh would get this far, Eisen says, more AGs would have signed on to the case—Racine, he says, “called it right.” The AG’s newest head-line-making suit, though, hasn’t earned him quite the same plaudits.

The action against Facebook goes to whether it misled DC residents when it allowed Cambridge Analytica—the political-microtargeting firm cofounded by Trump’s erstwhile campaign chief, Steve Bannon—to harvest users’ data for the 2016 presidential race. Though the firm was reportedly in violation of Facebook’s terms, the tech giant initially failed to notify its users of the mishandling of data.

Racine is suing on consumer-protection grounds and seeking three things: civil penalties, to make Facebook suffer for misleading DC residents; restitution, so locals can get a check for their hardship; and a court order preventing Facebook from ever pulling the same stunt again.

While the case is still in a nascent stage, the wider response so far has been more muted than it was to the emoluments fight. Racine is charging alone: No other AGs have signed on or filed a similar suit of their own.

“This is a naked attempt to raise his profile. It’s not going to help the people of DC.”

“This is a harder case than it seems,” says Berin Szoka, who leads TechFreedom, a cyberpolicy think tank. “I’m skeptical this complaint . . . [is] really going to go anywhere.” One problem is that Facebook users give away their data for free—an impediment to Racine’s argument for restitution. If Racine can show that users would have made a different choice had they known about the breach—switched accounts, for example, to MySpace—he might win. But that’s hard to prove.

Some tech lawyers think the bigger play is for history. Certainly, Silicon Valley feels this way. “This is a naked attempt by the attorney general to generate headlines and raise his profile,” says one tech insider in Washington who has followed the suit closely. “And it’s not going to help the people of DC.”

Racine went viral after the President name-checked him at a March meeting of AGs. “I feel like I know you,” Trump said. “I feel like I know you as well, Mr. President,” Racine quipped.

If there’s a prevailing criticism of Racine around the city, it’s that: an AG busy assembling a national platform while District residents squint to see the tangible benefit of cases like Facebook. “There was some anxiety and concern,” says DC Council member Charles Allen, a Racine fan, describing the doubts he’s heard in the past: “ ‘It’s an appropriate thing for an AG to do. But just because it’s appropriate, should you?’ ” Racine rejects this hypothetical and insists Facebook is a quintessential case of harm to local residents. “My strong hunch,” he adds, “is that we won’t be the only one who sues Facebook.”

Allen suggests another benefit of Racine’s marquee lawsuits, though—attention to DC. “When we talk about our ultimate goal of statehood,” says Allen, “Karl will be a big part of it.”

What does Karl Racine want? Follow him around to the community gatherings of half-interested audiences that pack his public schedule and it’s hard to miss the air of a local pol, putting in the patient, painstaking work of introducing himself to voters. Voters who might cast their ballot for the only higher city office available to the District’s AG: a Mayor Karl Racine.

But it’s not hard to picture him pivoting to higher office, either. Racine co-chairs the Democratic Attorneys General Association and has helped ramp up the group’s fundraising and profile, the better to compete against its Republican counterpart in races around the country. He’s also in line to become bipartisan president of the National Association of Attorneys General—a ceremonial position, but one with genuine cachet.

“I could see Racine possibly being the attorney general of the United States,” says DC Council member Elissa Silverman, something others around town have suggested as well. If this seems fanciful, Silverman offers a counterpoint. In the late ’90s, a former DC Superior Court judge was also talked about as a potential mayor: Eric Holder, who instead landed an appointment as US Attorney for DC, then climbed to the topmost rank at Justice. “I see Mr. Holder and Mr. Racine as not that different,” Silverman says.

Remarkably, Racine doesn’t laugh this off. “That’s a big job,” he sighs a bit theatrically as he leans back to gaze out the window, the Old Post Office glimmering at high noon. “I’m intrigued by the class of candidates running for President,” he eventually says, then adds, “I have a very close personal relationship with Senator Harris.” Racine met Kamala Harris through her husband, with whom he worked at Venable. The AG has been the beneficiary of two fundraisers hosted by the presidential hopeful from California—whom he has officially endorsed and who, by the way, is that state’s former attorney general.

For now, though, the District’s AG is preoccupied with his looming battles against the current President. According to reports this year, Racine has subpoenaed documents relating to Trump’s inaugural committee—the stirrings of a potential new inquest. Trump has given observers good reason to speculate whether the moves have wormed their way into his brain: At a meeting of attorneys general in the White House’s State Dining Room last month, the two rivals shared a notable exchange. “Hi, Karl,” the President said, grinning as he singled out Racine from the crowd. “I feel like I know you.”

“I feel like I know you as well, Mr. President,” Racine quipped.

Hardly anyone who knows Racine well can resist the irony. “The champion for the people that Donald Trump is persecuting is himself an immigrant!” says Frosh, describing the Shakespearean fortune of a presidency that could be imperiled by a refugee from a “shithole” country. “It’s appropriate—even complete, in an odd way.”

Racine never says as much outright. But as he gestures me out of his office, he stops at a piece of artwork hanging from the wall: a folk pastiche of the US flag, rendered in craggy, brilliant hues. Scrawled across the stripes, like the covert notes of a private journal, reads a faint message signed in ghostly gray: bring me your huddled masses / yearning to breathe free.

“This is what the United States is about, in my opinion,” Racine says, his eyes fixed on the painting. “I asked the artist to do me a favor.” He directs an uncurled finger toward the corner of the canvas. A dash of exuberant white—a bit brighter than the others—had been laid long after the paint was dry: an added star.

This article appears in the April 2019 issue of Washingtonian.