People who work for President Donald Trump typically meet one of two fates. They fail to show the unthinking loyalty he demands and get fired. Or, maybe worse, they don’t get fired—they endure the tantrums and turmoil and survive another day, binding themselves even closer to perhaps history’s most divisive president.
Anyone who went to work for Trump inside or outside the government surely knew the terms of the bargain. They’d be answering to an untested and impulsive president. They weren’t getting Dwight Eisenhower as a boss—they were getting Dwight Schrute.
Was it worth it? I asked nine seasoned officials, credentialed lawyers, flameouts, worker bees, operatives—some who voted for Trump twice, some who absorbed his harshest attacks. They all insisted that it was.
Plenty of Republicans refused to work for Trump. Those who signed up found various ways to justify their choices. A powerful mythology surrounds the presidency. Many see the Oval Office as the place where wars are won and economies rescued, making a job offer from the duly elected president an irresistible tug.
“The vast majority of people who worked in the White House were decent people who were doing the best they could to serve the nation,” John Kelly, the second and longest-serving of Trump’s four White House chiefs of staff, told me. “They’ve unfortunately paid quite a price for that in reputation and future employment. They don’t deserve that. They deserve better than that, because they kept the train from careening off the tracks.
“The climate—the work environment—is always set by the boss,” added Kelly, the retired Marine Corps general who left as his rapport with Trump deteriorated. “And people, generally speaking, endured it as long as they could. Until they couldn’t.”
Many of the people I spoke with drew a distinction when describing their work: It wasn’t the man they were serving, but the nation. (Trump often conflates the two, equating his interests with America’s). “I believed then and now I worked for the country,” Ty Cobb, who served as the chief White House lawyer handling the response to Robert Mueller’s Russia investigation, told me. “I didn’t really have any difficulty with that. People’s reactions were frequently hostile when they found out what I was doing. How hypocritical is it to think that the Democrats deserve the best people and Republicans don’t? I have served both. It’s the same country.”
Others argued that boycotting the Trump administration would have exposed the country to more harm. Even John Bolton isn’t sorry he took the job. Bolton—who was ousted last year as national security adviser, quickly became a target of Trump’s, and is now among the president’s most outspoken critics—saw himself as a bulwark against an untutored president. “He wasn’t prepared when he went in, and on January 20, he’ll be barely more prepared than when he started,” Bolton told me. Working on important national-security issues under Trump “really has added significance” because of the dangers the president posed. “That’s not to say that there’s a record of achievement—more a record of damage control. But that just highlights the reason to do it.”
From the start, motivations for joining Team Trump were complex. Public service may have been part of it, along with getting a platform to advance pet issues, such as the installation of conservative judges. But the job also has undeniable cachet. “There’s an allure to being part of the White House and working close to the president—even when that president is someone as despicable as Donald Trump,” Andrew McCabe, a former senior FBI official who took part in the bureau’s Russia investigation and was repeatedly disparaged by Trump, told me.
No one apart from Trump’s blood relatives could depend on his loyalty. Brad Parscale, the digital director for Trump’s 2016 campaign who was elevated to campaign manager for 2020, was part of Trump’s inner circle and became something of a celebrity in his own right. (At a rally in Minneapolis last year, I watched him wade through the crowd chatting with appreciative supporters, a campaign-staff entourage in tow.) But in July, Trump abruptly demoted him as Joe Biden built a strong lead in the polls. Two months later, Parscale, citing “overwhelming stress,” announced that he was leaving the campaign following a confrontation with police outside his Fort Lauderdale, Florida, home.
A person familiar with Parscale’s views told me that the campaign “took a toll on every aspect” of his life, and some of his own family members refused to talk to him because of his work on Trump’s behalf. He had thought that Trump was loyal to him too, but came away believing that the president had “hurt him,” said this person, who spoke on the condition of anonymity in order to be candid. Still, “half of America” feels it was “a great thing” that Trump became president in the first place, and Parscale helped make that happen. That’s justification enough for Parscale, who’s convinced the job was worth it, the person told me.
Like Parscale, Alan Dershowitz weathered a biting social backlash. The Harvard law professor emeritus, who spoke on the president’s behalf during his impeachment trial, has represented unpopular figures in the past—O. J. Simpson among them. Nothing compares to the fallout from defending Trump.
After Trump was acquitted, the 82-year-old got a letter from someone he knew telling him that the person could “no longer share society with you,” Dershowitz told me. An agent told his daughter, an actor, that she should change her last name if she hoped to get more roles. Dinner invitations have dried up—though that might actually be a blessing. “It’s so easy for me to socially isolate [during the pandemic] because no one wants to talk to me because I defended Trump in front of the Senate,” he said. “I lost 10 pounds on what I call the ‘Trump diet’ because no one invites me to dinner.”
So was it worth it? I asked. It was, he said. And in any case, “isn’t it better that he was thrown out of office by a vote for the people than by 100 senators?” Dershowitz said. “Isn’t that better for the country?”
An irony of the Trump era is that the same chaotic atmosphere and haphazard management that drove some aides out is what made the job attractive to others in the first place. Because Trump cycled through so many members of his staff, the survivors had ample opportunities to advance, and because Trump refused to heed gatekeepers, any number of aides wandering into view had a chance to talk to him directly. “I found the wide-open space exhilarating, and it got my adrenaline pumping every day,” Joe Grogan, who led the White House’s domestic-policy shop before leaving this spring, told me. (Grogan relayed a story in which the president randomly asked a deputy press secretary to help free the rapper A$AP Rocky from jail in Sweden. “You can do it,” Trump told the press aide. It’s not clear whether he was joking.)
Anthony Scaramucci was among those who initially rose in Trumpworld because of the president’s willingness to follow his own idiosyncratic hiring instincts. But just 11 days after “The Mooch” arrived in summer 2017—with a swagger and a mandate to stanch press leaks—he was gone, dumped after a profane call with a New Yorker reporter. Scaramucci describes his relationship to Trump as following a distinct parabolic arc. “Okay, this is an unsavory guy and a distasteful guy, and I probably shouldn’t be associated with him,” he told me. Then comes an acceptance that Trump is a fellow Republican who’s heading the party. “Now you’re looking for reasons to like him—and he does provide those reasons.
“He’s a charming person when he wants to be,” Scaramucci added. Yet there’s a “duality to his personality”—a “malevolent and dangerous” side.
Though he became part of the movement to jettison Trump, Scaramucci has no regrets. He reconciled with the person who fired him, Kelly, and said he learned something about himself—that he’s not cut out for a career in Washington. “I would never have learned any of those things if I wasn’t in the White House,” Scaramucci told me.
As a reporter, I’ve sometimes asked myself a version of the same threshold question: Is it worth spending so much time writing, reading, thinking, and talking about Donald Trump?
In 2018, my Wall Street Journal colleagues and I interviewed the president in the Oval Office. What could go wrong? We sat a few feet from him, our recorders spread out on the Resolute desk. We left and wrote our story, which included this quote: “I probably have a very good relationship with Kim Jong Un.”
The next day, we heard from the White House: Trump had not said that. We had missed the contraction I’d, a White House spokesperson insisted—the president was talking about a relationship that might blossom in the future. We listened to the audio over and over. We made it public and stood by our story. The White House released its own recording. Other reporters listened for definitive evidence of that hard, guttural d sound from the back of the throat, on which hung the state of U.S.–North Korean relations.
It was all pretty exhausting—and not the only run-in I’d have with Trump’s press operation. Were there better things to cover? Not when I considered the stakes. For the first time as a political reporter, I’d wondered if by the end of a president’s term our democracy would be standing. To me, the work was worth it. But I didn’t work for the man.