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In early March, a procession of lawyers in boxy suits and overcoats crowded into a chandeliered dining room at Tony Cheng’s in Washington, DC’s Chinatown. Justice Department attorneys passed heaping plates of beef with broccoli and spring rolls to corporate law firm partners and think tank fellows in bow ties. A sign taped to the restaurant’s entrance announced the event was sold out, and regulars of the Federalist Society’s monthly luncheon marveled at the turnout. The featured guest was Donald F. McGahn II, who had recently ascended to one of Washington’s most influential legal perches, White House counsel.

After the fortune cookies were distributed, C. Boyden Gray, a former White House counsel to George H.W. Bush and a Federalist Society board member, approached the microphone. McGahn was stuck at the White House dealing with a “pressing matter,” he informed the disappointed audience. Gray didn’t elaborate. He didn’t need to: The night before, the Washington Post had revealed that Attorney General Jeff Sessions, who had told the Senate that he had no contact with Russian officials during the presidential campaign, had in fact met twice with Russia’s ambassador.

Hours after the Federalist Society luncheon let out, Sessions recused himself from ongoing investigations into ties between the Trump campaign and Russia. President Donald Trump spent the next day fuming at his staff—particularly McGahn, who had to explain to the incensed commander in chief that Sessions’ recusal was the AG’s decision alone. Early the next morning, Trump rattled off a series of tweets accusing Barack Obama of wiretapping Trump Tower during the presidential campaign. McGahn was soon on a plane to Mar-a-Lago; his surreal task was to figure out how the administration might retroactively prove an explosive allegation that Trump had tossed out without evidence.

As the top legal adviser to the president, the White House counsel is one of the most vital positions in any administration. The counsel vets executive orders and nominees, reviews the legal aspects of national security matters, and monitors compliance with federal ethics laws. Rarely does an order or a memo leave the White House without the counsel’s sign-off. Gray says that during his time as counsel, his office received four times more paperwork than any other White House department. (This was before email.) A former Obama White House counsel told me, “People used to say to me, ‘You and the chief of staff are the only two people who really touch everything.'”

“He seemed mostly interested in grinding its work to a halt,” says a former FEC colleague. “Don had a blow-it-up mentality.”

Above all, the White House counsel’s role is to keep the president out of trouble, legal or otherwise. With Trump, that’s a Herculean task. McGahn has represented scandal-plagued Republicans—Tom DeLay was a client—but the controversy and chaos engulfing the Trump White House are another order of magnitude. McGahn represents the most conflict-ridden commander in chief in the nation’s history. He has spent his short time in the White House constantly rushing to put out fires.

On paper, McGahn, who is 48, wasn’t an obvious choice for White House counsel. He has never previously worked in a presidential administration, and he has all the attributes of the Washington elites whom Trump has denounced. (One attendee of McGahn’s 2010 wedding says it was like “a convention for election lawyers.”) Trump vowed to get big money out of politics, while McGahn has spent much of his legal career helping candidates and donors stretch the limits of campaign finance laws. “The irony is that Trump campaigned on ‘draining the swamp,'” says Dan Weiner, a lawyer at the Brennan Center for Justice, “but it’s my impression that Don thinks the ‘swamp’—at least as many good-government types would define it—is necessary and constitutionally protected.” (McGahn did not respond to multiple requests for comment.)

Yet on another level, McGahn is ideally suited for a job in the Trump White House. The administration’s deregulatory agenda—the “deconstruction of the administrative state,” as chief strategist Stephen Bannon put it—is perfectly in sync with McGahn’s libertarian views. To carry out that mission, he has put together a team of nearly 30 lawyers, many of whom are experts in federal law and how to unravel it. McGahn has plenty of experience dismantling the bureaucracy from within: That was precisely the program he pursued for five years while serving on the Federal Election Commission. “He didn’t care about the institution, and he seemed mostly interested in grinding its work to a halt,” says David Kolker, a former associate general counsel at the FEC who worked alongside McGahn. “Don had a blow-it-up mentality.”

Before recent renovations, visitors to the ninth floor of the FEC’s headquarters, where the commissioners have their offices, were greeted by a wall of black-and-white photographs—headshots of all 23 commissioners who had served the agency since its founding in 1975. All except one.

McGahn, who was on the FEC from 2008 to 2013, had refused to sit for his official photo. It was his way of dispelling the notion that he had any affinity for his employer. The way he saw it, he was reining in an overzealous bureaucracy that trampled the rights of ordinary Americans. No commissioner has done more to change the agency.

In the late 1990s and early 2000s, McGahn carved out a niche as the go-to lawyer for House Republicans and spent nearly a decade representing the National Republican Congressional Committee, the political arm for House Republicans. When House Majority Leader Tom DeLay was accused of ethics violations, partly in connection with the Jack Abramoff lobbying scandal, McGahn led his legal defense. (DeLay resigned from Congress but was exonerated in 2013.) In 2005, McGahn hung his own shingle and built a modest practice focusing on election-related cases. (He’d convinced the NRCC to keep him on retainer as its general counsel—an unorthodox and lucrative arrangement.) He developed a reputation as a fierce ideologue with a deep understanding of the law, but within the clubby network of election lawyers, he cut an odd figure. He lacked an Ivy League pedigree, wore his hair long, and spent weekends playing guitar in local rock bands. (His latest, Scott’s New Band, which advertised itself as “one of the Mid-Atlantic region’s most exciting and flat-out FUN cover bands,” split up in December as McGahn prepared to enter the White House.) “He is kind of an iconoclast,” says James Bopp, a prominent conservative election lawyer.

Republicans had floated McGahn in the 2000s to fill an open seat on the FEC. He never hid his disdain for the independent agency—a perspective that undoubtedly appealed to lawmakers who thought of the agency as a nuisance. “The original intent was for it to be a glorified congressional committee,” he said in 2001. Nodding to the fact that the commission is appointed by the same people—members of Congress—whom it regulates, McGahn acknowledged that “you have the charge of the fox guarding the hen-house.”

Congress designed the FEC to ensure bipartisanship, mandating that the six-member commission have no more than three members from either party. The commission can’t act without a four-vote majority. But in 2008, in what some commissioners call the “dark ages,” it was down to two members. Without a quorum, the agency could do little more than run its website and keep the lights on.

Senate leaders Harry Reid and Mitch McConnell cut a deal in the summer of 2008 to end the FEC’s impasse when they confirmed a slate of new commissioners, McGahn among them. From the beginning, McGahn made clear he felt no kinship with his new employer. “A lot of the staff said, ‘Welcome to the agency. It’s so nice to have you join us,'” recalls Eric Wang, an election lawyer who got to know McGahn while working for another Republican commissioner. “He made a point of saying, ‘I’m not joining you,'” making it clear that he was not there to collaborate with the career agency staff, but rather to serve as a check on them.

The FEC has always suffered from partisan infighting. Still, former Democratic and Republican commissioners say they largely viewed their job as enforcing the law and finding four-vote majorities on the cases before them. That seemed to change with the arrival of McGahn and his two Republican colleagues, Caroline Hunter and Matthew Petersen, according to Ellen Weintraub, the FEC’s most senior Democratic commissioner, who recalls that they kept their deliberations to themselves and voted as a bloc. The first time Weintraub witnessed this, she thought, “What? You have one brain for the three of you?”

McGahn was seen as a domineering force on the commission. “There is no nice way to say it: At some point, McGahn will be an asshole,” conservative lawyer Steve Hoersting warned newly confirmed Commissioner Petersen in a 2008 email. “He’ll insist he knows the better course on an issue and will insist you go along. Don likes to employ the ‘trust me’ method of persuasion.”

Weintraub says it was nearly impossible to pry any information out of McGahn, who refused to return her messages or reply to her emails. He rarely seemed to be in his office. Once, Weintraub bumped into his executive assistant in the women’s restroom. “She looked at me, and without even a hello she blurted out, ‘He’s not in, I don’t know when he’s going to be in, I don’t know when I’m going to be talking to him.'”

To his critics, McGahn was on a one-man crusade to destroy the FEC from within. An analysis by the good-government organization Public Citizen found that the number of deadlocked enforcement votes spiked after his arrival, from an average of 1 or 2 percent in the early and mid-2000s to 15 percent in 2011. McGahn had no qualms about undermining the FEC’s nonpartisan lawyers—in one case, he posted a memo to the agency’s website contradicting the commission’s attorneys in an ongoing lawsuit. He bragged about disregarding parts of the law he disputed or saw as out of sync with court rulings. “I’m not enforcing the law as Congress passed it,” he told a group of law students in 2011, referring to the McCain-Feingold Act of 2002, which was partially invalidated by the 2010 Citizens United ruling. “I plead guilty as charged.”

Former FEC employees say McGahn’s hostility to the agency sometimes extended to its staff. Lawyers from the Office of the General Counsel—which issues recommendations to the commission and defends the FEC in lawsuits filed by outside parties—got the worst of it. When junior lawyers appeared before the commissioners in closed sessions, McGahn could be brutal, former FEC employees say. “I remember passing my boss notes saying, ‘Make him stop,'” one former executive assistant told me. “He would pick on not the supervising attorney, but the line attorney—like a cat would play with a mouse, swatting him.” McGahn, former colleagues recall, saw the career employees as liberal do-gooders, and he made it his mission to rein them in. “He would berate the staff,” says a former FEC lawyer. “He said they came to certain conclusions because they favored the Democrats.”

The FEC’s lawyers enjoyed an open line of communication with the Justice Department. The two agencies often worked different sides of the same cases—the DOJ handled the criminal side while the FEC handled the civil. Near the end of his tenure, McGahn pushed for changes to the agency’s enforcement manual so the Office of General Counsel couldn’t share information with other federal agencies without the commission’s approval. McGahn also sought to require FEC lawyers to get four votes on the commission before accessing publicly available information—such as news clips and old lawsuits—in enforcement matters. Allies of McGahn say these moves were intended to bring order to an out-of-control bureaucracy. (Both efforts were unsuccessful, though his proposals have since become de facto policy at the commission.) FEC lawyers saw McGahn’s efforts as an attempt to handcuff them. The FEC’s general counsel at the time, Anthony Herman, quit in frustration.

“He is not a lawyer who says, ‘You simply are unable to do X.’ He’ll look for every single type of way to be able to do X.”

McGahn left the commission in September 2013 and returned to private practice. If his goal was to paralyze the nation’s election watchdog, he largely succeeded. Deadlocked votes continue. Enforcement actions and assessed fines have dropped. (The Republican commissioners tout these statistics as evidence that more candidates and committees are following the law, while Democrats say they’re proof of the agency’s failure to act.) The commission has gone more than three years without naming a new general counsel, and Congress hasn’t confirmed any new members since 2013, with one current member’s term having expired as many as 10 years ago. A 2016 survey of federal employees found that morale at the FEC was at its lowest ever. Ann Ravel, a Democratic commissioner, recently resigned two months early, weary of the FEC’s dysfunction.

McGahn is not solely at fault for the FEC’s sorry state—but those who worked alongside him or observed his time there say he deserves much of the blame. “He ushered in a strategic approach to gridlocking that agency,” says David Donnelly, president of the election reform group Every Voice, “because if an agency can’t do its job, it can’t enforce the law.”

In late 2014, McGahn met Donald Trump for the first time. He was now a partner at Jones Day and had taken on high-profile conservative clients, including the political action committee of the billionaire Koch brothers and Citizens United, the nonprofit group behind the monumental Supreme Court ruling of the same name. David Bossie, the head of Citizens United, had hired McGahn to spearhead a lawsuit against New York Attorney General Eric Schneiderman to block disclosure of its donors. (The suit ultimately lost.) As Trump mulled a presidential run, Bossie recommended McGahn as a campaign lawyer.

According to a person familiar with the meeting, McGahn reminded Trump that they had a personal connection. In the early 1980s, when the real estate mogul wanted to muscle his way into the fledgling casino industry in Atlantic City, New Jersey, he hired McGahn’s uncle Patrick, a local lawyer and political power broker. A three-time Purple Heart recipient nicknamed Piano Wire Paddy for his weapon of choice in the Korean War, Paddy McGahn and his brother Joe, a Democratic state senator, had been instrumental in bringing casino gambling to Atlantic City. Paddy, who died in 2000, paved the way for Trump’s Atlantic City expansion. When a Trump executive complained at the time about his high legal fees, Trump reportedly said, “Jack, I’m 13 and 0 with this guy.”

By the time Trump opened his first casino in 1984, however, the McGahns had undergone a conversion. Tired of operating under Paddy’s thumb, the state assemblyman for Atlantic City, Steven Perskie, had challenged Joe McGahn for his state Senate seat in 1977. The Democratic machine threw its weight behind Perskie (McGahn ran as an independent), and Perskie won the election—a betrayal in the eyes of the McGahn family. Thereafter, the McGahns were Republicans.

Don McGahn, who grew up in Atlantic City, was one of Trump’s earliest campaign hires. The lawyer, though, didn’t bet entirely on Trump. In March 2015, he also took on another client: former Texas Gov. Rick Perry’s leadership PAC, seen as a vehicle for a Perry presidential run. It is not uncommon for rival candidates to be represented by lawyers at the same law firm, but rarely does the same attorney work for more than one contender, according to election lawyers I spoke to.

McGahn was in attendance for Trump’s official campaign announcement in the rose-marble lobby of Trump Tower in June 2015. It was a landmark moment in a lucrative partnership. According to an election lawyer I talked to, a presidential campaign typically pays a flat fee in the range of $25,000 to $35,000 a month for legal representation. Jones Day, according to a former Trump staffer, instead billed the campaign on an hourly basis, racking up monthly bills of as much as several hundred thousand dollars. “For the guy who wrote The Art of the Deal, Trump got totally screwed on the deal with Jones Day,” the election lawyer told me.

McGahn came to play an integral role as the race wore on. In November 2015, he beat back an attempt by the former chair of New Hampshire’s Republican Party to keep Trump off the ballot in the state. As Trump delivered his victory speech in Manchester, a beaming McGahn stood onstage with the Trump family. And it was McGahn who introduced Trump to Leonard Leo, the Federalist Society executive who oversaw the Trump campaign’s assembly of two lists of potential Supreme Court nominees as a way to win over skeptical Republicans. Polls show that Trump’s picks played a key role in convincing social conservatives to hold their noses and vote for him.

For a campaign with no shortage of drama, McGahn proved remarkably adept at ducking attention. In a rare on-camera interview with a right-wing TV network called the One America News Network on the floor of the Republican National Convention in Cleveland, he predicted that Trump would defeat Hillary Clinton and claim the presidency in November. Asked what Trump would say in his RNC acceptance speech, McGahn grinned. “I wouldn’t dare begin to guess.”

One day this winter, C. Boyden Gray passed the scrum of photographers camped out in the lobby of Trump Tower and rode the elevator up. McGahn, now the White House counsel-to-be, had sought his advice on how to represent the most unorthodox president in perhaps all of American history. Their conversation focused on the massive ethics conundrums facing President-elect Trump, Gray told me. He’d tackled ethics questions himself while working as White House counsel for George H.W. Bush, who made a fortune in the oil industry, but “I didn’t have anywhere near the complexities that Don McGahn had,” he says.

Those who know McGahn see his influence at play in the White House’s laissez-faire approach to ethics and its insistence that conflict-of-interest rules don’t apply to Trump. Trump has refused to divest from his business holdings, raising the possibility of self-enrichment by virtue of the office and violations of the Constitution’s Emoluments Clause, which prohibits a president from accepting payments from foreign governments. Trump told the New York Times in November that a sitting president “can’t have a conflict of interest” and that the law was “totally on my side.” The idea that conflict-of-interest laws don’t apply to the president “is vintage McGahn,” a former colleague told me.

McGahn’s hiring choices to oversee Trump’s sprawling ethics portfolio may be telling. As his top deputy in charge of compliance and ethics, he brought on Stefan Passantino, a lawyer perhaps best known for representing former House Speakers Newt Gingrich and Dennis Hastert in their respective ethics scandals—Gingrich for using tax-deductible money for political purposes and submitting false information to House investigators, and Hastert for failing to properly disclose that he’d paid legal bills with campaign funds in connection with the congressional page scandal. (Years later, Hastert admitted in court to abusing young boys and was sentenced to 15 months in prison for illegally paying hush money to one alleged victim.) Under McGahn, as Politico reported, the White House eschewed the traditional ethics briefing for senior staffers. After the nonpartisan Office of Government Ethics recommended that Trump adviser Kellyanne Conway be reprimanded for promoting Ivanka Trump’s clothing business, Passantino refused, arguing that many federal ethics laws don’t apply to White House employees. OGE Director Walter Shaub Jr. countered that Passantino’s assertion “cites no legal basis” and “is incorrect.”

Ethics haven’t been the only issue dogging McGahn and the counsel’s office. The chaos surrounding Trump’s January 27 travel ban raised the question of whether McGahn was in over his head. His attempt to clarify the order via a legal memo in federal court was panned by outside legal experts, and his case was not helped when Trump went on a Twitter tirade against the “so-called judge” who had made a “ridiculous” ruling. (If McGahn did urge Trump to curb his attacks on the judiciary, Trump didn’t listen: After the administration’s revised immigration order was blocked in court in March, Trump called the ruling “terrible” and “done by a judge for political reasons.”)

A more experienced counsel, say ex-White House lawyers and other legal experts, would have consulted federal agencies before releasing such an explosive order and stopped the president from launching verbal assaults against members of the judiciary. “One person who must bear responsibility for the awful rollout of the EO is White House Counsel Donald McGahn,” Jack Goldsmith, a former assistant attorney general at the Justice Department under President George W. Bush, wrote on the website Lawfare. If McGahn had tried to restrain Trump and failed, Goldsmith argued, then he was ineffectual; if he had not attempted to corral Trump and correct the flaws in the immigration order, he was incompetent.

Still more questions were raised about McGahn’s judgment and the White House’s vetting process when the Washington Post reported that national security adviser Michael Flynn had discussed sanctions with the Russian ambassador to the United States, and that the Justice Department had briefed McGahn about it during the transition. The next day, White House press secretary Sean Spicer told reporters that McGahn had conducted his own review and “determined that there is not a legal issue.”

Former White House lawyers were stunned. “I wouldn’t have done that,” a former Obama White House counsel told me. “I don’t know what the FBI knows. I don’t know who they’re interviewing.” Goldsmith, the former senior Justice Department lawyer, questioned how rigorous McGahn’s review could have been. The White House counsels he knew, Goldsmith wrote, “were all tough-minded but extremely prudent in dealing with legal jeopardy related to the White House, especially if that jeopardy touched someone as close to the President as his National Security Advisor.” He added, “It is far from clear that the current White House counsel has acted in this fashion.” And McGahn’s judgment was once again called into question when news reports revealed that Flynn had worked as a foreign agent on behalf of Turkish interests at the same time he served as Trump’s national security adviser—a troubling conflict that the incoming White House counsel was briefed on but declined to address.

In late March, two of McGahn’s underlings in the counsel’s office were reported to have helped supply classified intelligence reports to Rep. Devin Nunes (R-Calif.), chair of the House intelligence committee, in an attempt to support President Trump’s unfounded allegation that his predecessor had wiretapped him. The revelation raised questions about whether McGahn had played any part in this effort.

The mark of a great White House counsel, experts say, is providing sound legal advice to the commander in chief whether he wants to hear it or not. But with McGahn, the evidence so far—the lax approach to Trump’s ethics problems, the execution of the immigration order, the Flynn imbroglio—suggests a loyal lieutenant eager to please the president. “Don is an expert. He is not a lawyer who says, ‘You simply are unable to do X,'” a former Trump campaign aide told me. “He’ll look for every single type of way to be able to do X.” Which, in the end, may be the last thing this president needs.