The permanent outsider

President Trump has no idea how to run for reelection as an incumbent
Gabriel Alcala for The Washington Post

At a White House signing ceremony this month, President Trump lamented the “deep-swamp things happening” in the nation’s “deep state.” Speaking to workers at a Whirlpool plant in Ohio a few days later, he promised to “drain the Washington swamp once and for all.” There’s just one niggling complication: More than 3 1 / 2 years into his presidency, Trump is the straw-haired avatar of the swamp.

Ashley Parker @AshleyRParker is a White House reporter for The Washington Post. She joined The Post in 2017, after 11 years at the New York Times, where she covered the 2012 and 2016 presidential campaigns and Congress, among other things.

Typically, presidents run for reelection on the achievements of their first term: the policies deployed, the gains notched, the victories achieved, the goals to fully realize in the next four years.

But Trump has, from that first golden-escalator ride, campaigned, governed and wallowed in grievance, never once wavering from his outsider ethos. He is relentlessly on brand about the forces arrayed against him. He warns his supporters not to trust the "FAKE NEWS" and demands that states and districts "OPEN THE SCHOOLS!!!" He suggested this spring that Michigan, Minnesota and Virginia "LIBERATE" themselves from the restrictive coronavirus protection measures his own public health officials had suggested.

It is not unusual to run for office on those terms, from the outside. But Trump appears unwilling — or unable — to abandon his burn-it-all-down cri de coeur, even when the establishment he lambastes is run by himself and his appointees. He insists firmly, and implausibly, that while he may be in Washington, he is not of it. Refusing to take ownership of his own administration's record allows Trump to jettison responsibility.

Yet the decision to position himself as a permanent outsider is less strategic than pathological, say people close to the president, reflecting a man who since childhood has lusted after an elite that never truly welcomed him. Trump is "a significantly more evil version of Gatsby," said Tony Schwartz, the co-author of Trump's 1987 bestseller, "The Art of the Deal," alluding to F. Scott Fitzgerald's antihero, who hungers for the American Dream and briefly achieves it through dishonest means.

As a young developer with his father in Queens, Trump longed for the glitz of Manhattan. Yet when he finally arrived there, he was dismissed as crude and gauche. He became a boldfaced name at public events, yet rarely received more coveted invites to small dinners at the homes of the city's one percent. He bought Mar-a-Lago, his gilded club in Palm Beach, Fla., in part because he wasn't welcome at the other members-only clubs.

Schwartz, who has since become an outspoken critic of the president, recalled Trump's book party for "The Art of the Deal" in late 1987, at Trump Tower. He estimated that 300 or 400 people showed up, but the guests were largely C-list celebrities, "the people who would have maybe been on 'Celebrity Apprentice,' " Schwartz said.

And before Trump mounted his quixotic presidential bid, Beltway wise men largely viewed him as a politically incorrect fool, a showman who often flirted with running for president but who would never actually launch a campaign — let alone win. President Barack Obama roasted him brutally as a buffoon who didn't understand politics at the White House Correspondents' Association dinner in 2011.

Trump's sense of himself — as an outsider with something to prove — doesn't just propel him. It also binds him to his core supporters, who also feel spurned by the establishment. "His appeal to his base — and it's such a visceral one — is largely through the shared experience of feeling aggrieved, feeling like they're not being treated fairly," Schwartz said. He is especially popular among white evangelical Protestants (71 percent approve of his performance), white men without college degrees (59 percent) and rural Americans (59 percent), according to a Washington Post-ABC News national poll released last weekend.

President Trump addresses a crowd at a campaign event at North Star Aviation in Mankato, Minn., on Aug. 17. Trump’s anti-establishment appeal remains popular in rural areas and small towns like Mankato. (Joshua Lott/For The Washington Post)

Truthfully, Trump did not take naturally to Washington, nor to the levers of the presidency. He remained wary of the vast bureaucracy. He questioned his own intelligence community, skeptical of CIA and FBI findings, especially those he viewed as undermining his legitimacy or his pronouncements. He mistrusted many of his own officials, both career civil servants and those who hailed from the Republican National Committee and the party establishment. Now, amid the coronavirus pandemic — which has left more than 170,000 Americans dead — Trump even finds himself at odds with apolitical public health officials.

Trump’s 2016 campaign was a clear assault on the political elite, an us-vs.-them anvil of a message. He painted former secretary of state Hillary Clinton, his rival, as a corrupt Washington insider — an attack his team now hopes to reprise on former vice president Joe Biden, his Democratic opponent, who was elected to the Senate at 29 and whose political career spans more than four decades.

But deploying the same argument against Biden that he used against Clinton is harder, even Trump's allies concede, now that he's been in office for nearly a full term. "I do find it kind of funny that he makes that argument that this is Joe Biden's America and the country is on fire," said one outside adviser, speaking on the condition of anonymity to share a candid assessment. "Well you're the president, so I guess it's kind of your America right now."

Recently, even in interviews with friendly media outlets, the president has struggled to articulate his top priorities should he win a second term. When Fox News's Sean Hannity asked him about this in June, Trump betrayed the difficulty of running against the establishment. He boasted about his "experience," explaining that while he had never even spent the night in the nation's capital before his election, "now I know everybody." He had come full circle, becoming the self-described politeratti he disdains.

Trump seems to know that his outsider ethos is a kind of performance. As president-elect, he regaled a crowd in Des Moines with the genesis of his "Drain the swamp" rally chant: When aides first suggested the slogan, he hated it, but when he used it in front of an audience, the "place went crazy." So he said it again, and again. "Then I started saying it like I meant it, right?" Trump said.

This anti-establishment tone is nothing new, of course. Former president Jimmy Carter, a peanut farmer from Georgia, made an asset of the fact that he'd never held office in Washington when he ran for president in 1976. Former president Ronald Reagan, too, who defeated Carter just four years later, played up his Western roots, turning his comfort — and rugged good looks — in a cowboy hat into an advantage.

But neither man was president at the time he made this pitch, and running for reelection often requires an adjustment, most typically by touting achievements from the previous four years.

There is no clear historical example of a sitting president running as a total outsider, said Kathryn Brownell, an associate history professor at Purdue University and the author of “Showbiz Politics: Hollywood in American Political Life.” Even Richard Nixon — who, like Trump, campaigned in 1968 on the idea of law and order, offered a dark vision of American carnage and was “very anti-media, very suspicious of the bureaucracy” — ran for reelection presenting “a very cheery version of all of his accomplishments,” Brownell said.

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