Politics & Policy

Donald Trump: The Art of Self-Sabotage

(Scott Olson/Getty)

Reporters aren’t supposed to engage in psychological speculation. But Donald Trump’s series of extraordinary statements this week — on abortion and the Geneva Conventions, criticizing Wisconsin governor Scott Walker for not raising taxes, and attacking the character of a reporter his campaign manager has been arrested for manhandling — make such speculation inevitable. 

“The number of people who have emailed me asking me if I think Trump is trying to do himself damage intentionally isn’t small,” tweeted Maggie Haberman of the New York Times. “Trump is playing into his opponents’ memes — phony, unprepared, hostile to women, unelectable, not a Republican, sloppy, vindictive, chaotic,” added Mark Halperin of Bloomberg News.

In a taped interview he gave to business journalist Michael D’Antonio for his book Never Enough: Donald Trump and the Pursuit of Success, Trump himself admitted, “I don’t like to analyze myself because I might not like what I see.” D’Antonio’s conclusion in the book was that “Trump was willing to say and do almost anything to satisfy his craving for attention. But he also possessed a sixth sense that kept him from going too far.”

But what if Trump’s “sixth sense” is now failing him, because part of him doesn’t really want to win?

Trump admits that for months he vacillated on running. The Washington Post quoted him this week as saying of his decision to run: “It was a 50–50 chance. We were thinking about it. A 25 percent chance even. Because I give up a lot when I run. I gave up a life.”

Last year, Stephanie Cegielski agreed to become communications director of a pro-Trump super PAC that was later shut down over allegations that it was illegally coordinating its activities with the campaign. Cegielski has since turned on Trump and this week wrote an impassioned article describing how Trump’s own staff intended for him only to place second in the primaries and have a major impact on the GOP race: “I don’t think even Trump thought he would get this far. And I don’t even know that he wanted to, which is perhaps the scariest prospect of all. He certainly was never prepared or equipped to go all the way to the White House, but his ego has now taken over the driver’s seat, and nothing else matters.”

Cegielski’s views are confirmed by Cheri Jacobus, a GOP strategist who had meetings with Trump’s campaign about becoming its communications director. “I believe Trump senses he is in over his head and doesn’t really want the nomination,” she told me. “He wanted to help his brand and have fun, but not to be savaged by the Clintons if he’s the candidate. He wouldn’t mind falling short of a delegate majority, losing the nomination, and then playing angry celebrity victim in the coming years.”

To all outward appearances, Trump seems to be engaged in a form of self-sabotaging behavior.

To all outward appearances, Trump seems to be engaged in a form of self-sabotaging behavior in which people both move toward a goal and then from deep within do things to defeat themselves.

Even Trump’s friends are wondering what’s going on. “I can tell you, having worked for Trump for almost forty years, on and off, no one puts words in his mouth,” longtime Trump strategist Roger Stone told GQ magazine this week. “Trump is better than his campaign. . . . So only Trump can tell you why Trump does the things Trump does.”

Last fall, as Trump rose to giddying heights in the polls, a group of his staffers sat around the office imagining what the reaction of their boss would be if he actually won the presidency. One told me: “We concluded that he really would say, ‘Guys, what did you do to me? I had a great life. Now I have to move to the White House?’”

The anecdote is reminiscent of the last line of the famous 1972 movie The Candidate. Robert Redford plays Bill McKay, a novice who has just won a surprise victory for a Senate seat. In a daze, he pulls aside his campaign manager and asks, “What do we do now?”

No one knows how the Trump drama will play out, but if indeed he contributes to his own loss of the nomination the consequences for politics will be, to borrow a Trump word, sad. The legitimate anger and cynicism toward Washington that is felt by many of his supporters may be channeled into unproductive behavior and their alienation only enhanced. Far from Making America Great Again, Donald Trump might wind up leaving his supporters even more powerless and feeling like Trump’s Chumps.

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