Trump's Campaign Succeeded by Breaking All the Rules—and It’s Catching Up to Him Now

Recalling his victory over Hillary Clinton has been the president’s only solace for months, but his personnel and management decisions now threaten to topple his presidency.

Carlo Allegri / Reuters

Donald Trump’s campaign for president seemed to vacillate between, to borrow Hunter S. Thompson’s dichotomy, being too weird to live and too rare to die. All the smartest analysts were convinced that it was definitely too weird to live. Stocked with amateurs, retreads, and minor-league washouts suddenly promoted for a cup of coffee, and overseen by a candidate with a penchant for enormous gaffes. The Trump team was widely viewed as on the verge of collapse. The joke was on the wise analysts: The candidacy turned out to be too rare to die, and now Trump is president.

But with a few months’ extra perspective, and after several days of damaging revelations, it’s becoming clear that although Trump’s chaotic approach to the campaign did not prevent him from winning the White House, and may actually have provided him with a crucial edge, it is hobbling his presidency. The undisciplined, untutored atmosphere is on display in the meeting that Donald Trump Jr., Jared Kushner, and Paul Manafort had with a woman they believed to be a Russian government lawyer offering opposition research on behalf of the Kremlin, and there may be more damaging revelations to come.

Politico reported on a bleak atmosphere inside the administration Tuesday night: “One Trump adviser said the White House was ‘essentially helpless’ because the conduct happened during an ‘anything goes’ campaign that had few rules.”

The June 9, 2016, meeting with attorney Natalia Veselnitskaya exemplifies many of the traits of the Trump campaign that are causing trouble now. There were three people in the meeting. Two of them were close relatives of the candidates (Kushner by marriage to Ivanka Trump), neither of whom had ever worked on a political campaign before. The presence of these rookies might explain some of the clear errors they made. Campaign veterans on both sides of the aisles have reacted with horror to the disclosure of the meeting, saying that if they were offered opposition research by someone presented as a foreign agent, they would contact the FBI. Instead, Trump Jr. replied, “if it’s what you say I love it especially later in the summer.” Which points to the second rookie error: creating a paper trail of emails that could be incriminating later on. (The June 9 meeting only became known when Jared Kushner belatedly disclosed it, having earlier left it off a form when applying for security clearance, another no-no.)

The third Trump official in the room was Paul Manafort. As a veteran political operator both in the United States and abroad, Manafort certainly should have known better. (A source close to him told Politico he hadn’t read the email chain where Veselnitskaya was identified as a “Russian government lawyer.”) But Manafort exemplified the other sort of tendency: Trump’s readiness to grab onto oddballs and retreads. Manafort joined the campaign first to help with delegate counting at the convention—drawing on expertise from a floor fight way back in 1976—but quickly muscled his way into a more powerful role. This made some sense, since he was one of the few experienced figures in a flailing campaign (most experienced GOP operatives refused to work for Trump), but Manafort brought a great deal of baggage with him. Much of his career was spent working for unsavory foreign leaders, most recently the Vladimir Putin client and Ukrainian President Viktor Yanukovych, deposed in a popular 2014 revolt. Manafort had also done business with various Kremlin-linked oligarchs, and documents show he had once a contract to boost Putin’s standing in the U.S.

Mysteriously—in what should have been another red flag for Trump in the hiring process—Manafort was willing to work for free. It’s difficult to believe that someone who has made a good living working for deeply disliked politicians would suddenly decide to work pro bono for a presidential candidate, especially one with no particularly strong ideological convictions for Manafort to latch onto. So what was Manafort’s game? It’s not clear, though there are multiple investigations into him, which might eventually answer the question. Some questions have focused on his use of shell corporations to purchase millions of dollars in New York City real estate, as well as dealings in Cyprus, both of which share characteristics with money-laundering schemes. After leaving the campaign in August, Manafort also received huge loans from Trump friends.

Manafort’s ascendance coincided with the fall of campaign manager Corey Lewandowski, another hire who also exemplified Trump’s tendency to choose employees on the basis of availability and loyalty more than skill or experience. Lewandowski was a wash-out from New England politics, but he was fiercely devoted to Trump. Eventually, though, he got shoved out. There were various factors: He had created an embarrassing distraction when he grabbed a reporter at an event in Florida, then lied about it, and the campaign was struggling. More importantly, however, he had reportedly fallen afoul of Trump family members, who exerted an unusually strong influence on the candidate and pressed for Lewandowski’s ouster.

Campaign staffers, then, tended to be either untutored, of questionable scruples, unvetted, or unfireable by virtue of family ties—or to possess several of those traits in combination. Trump approached the campaign much like he has approached his business career, with a willingness to hire people who would move fast and break things. The problem is that the things that get broken are often laws. In business, you can sometimes beg off, pay a fine, or settle a claim, but that doesn’t work as well in the high-pressure political spotlight.

If the June 9 meeting epitomized these problems, it may not be the last such episode. Take the Trump team’s digital operation. The team was viewed not so much as a joke as entirely nonexistent until a BusinessWeek story by Joshua Green and Sasha Issenberg in late October. The article revealed that Brad Parscale—you guessed it, a little known digital marketing figure without campaign experience—had overseen the construction of a team in San Antonio. When Trump won, this team won sudden praise for its stealth success.

Did it deserve that praise? McClatchy reported Wednesday that House and Senate investigations as well as Special Counsel Robert Mueller’s team are looking into whether Jared Kushner, who oversaw Parscale’s operation, coordinated with Russian agents to point them to where to target propaganda operations so as to best influence the election to aid Trump. They also want to know whether the Trump campaign had any role in releasing hacked emails from the Democratic National Committee and Clinton campaign chair John Podesta’s account.

“There appears to have been significant cooperation between Russia’s online propaganda machine and individuals in the United States who were knowledgeable about where to target the disinformation,” Mike Carpenter, a former Pentagon Russia hand, told McClatchy. The article did not allege that any investigation has uncovered clear evidence of such coordination.

The campaign scandals are not Trump’s only problems. He has hundreds of unfilled executive-branch jobs, most of them without nominees. His foreign policy has been chaotic at best, even setting aside problems that have bedeviled several of his predecessors, especially North Korea’s nuclear problem. On the home front, he has not notched a single major legislative win yet, and his executive orders have a miserable record in court. But it is the campaign scandals—and his firing of FBI Director James Comey, which he says was in response to the FBI’s Russia investigation, and which has raised questions of obstruction of justice—are the gravest threat to his presidency. The irony, of course, is that if the Trump campaign really did conspire with Russia to interfere in the election, and that swayed the result, then he also wouldn’t be president without that same motley assortment of staffers.

How truly different is the Trump administration from the Trump campaign on staffing? Certainly, there are more veteran hands at the White House than there were at Trump Tower. But the president has also seen multiple hires withdraw nominations or leave jobs without security clearances due to improper vetting. It’s an open question to what extent the same lack of discipline that dogged the campaign affects the White House.

As Trump’s presidency has gotten bogged down in scandal and legislative morass, it has become apparent that he’s deeply unhappy in his new job. He complains that it’s harder than he thought, and that he loved running his business. Talking about the campaign has been his one solace, a chance to think back to a time when he disproved the haters and losers, upset a heavy favorite, and triumphed. Given the troubles that the campaign is giving him now, it will be interesting to see how long that lasts.