An honest question: If Donald Trump were trying to lose the presidency, what would he have done differently? Not much, if you ask me.
No, I’m not suggesting Trump wants to lose so he can be a martyr and quit having to do any real work. This theory, which I see as the triumph of hope over optimism, continues to persist (at some points, the hope has gone so far as to suggest that Trump might even resign). Trump wants to win. It’s just that he’s pursuing a strategy that will probably guarantee he doesn’t.
Consider a checklist of recent decisions: He’s trailing in the polls, but he decided to withdraw from a debate because the organizers wanted to make it virtual. With just weeks to go before Election Day, he publicly walked away from a COVID-19 relief bill (until “after the election”) that would have sent government checks to desperate Americans. During a recent debate, he told the Proud Boys to “stand back and stand by,” and during Thursday night’s televised town hall, he refused to criticize the QAnon conspiracy theory (CHECK, CHECK, CHECK!).
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But this is nothing new. From day one, Trump has never cared about growing his coalition, and instead has pursued policies and rhetoric guaranteed to alienate potential supporters. Trump started his administration with a “Muslim ban” (instead of an infrastructure bill) and is ending his re-election campaign by walking away from a COVID-19 relief deal. In between a million chaotic things happened.
That’s not to mention that he continues to say and tweet crazy things—things like attacking Maine Senator Susan Collins, earnestly sharing a story from a satirical website, and (my favorite) retweeting “a conspiracy theory that Joe Biden orchestrated to have SEAL Team...killed to cover up the fake death of bin Laden,” which can only serve to alienate college-educated suburban women, for example.
Could it be that his experience in business taught him the amoral lesson that you never turn away a customer—that a bird in the hand is worth two in the bush (which explains why he won’t criticize white nationalists, even if refusing to do so means he won’t be able to attract college-educated suburbanites)? If so, he might be applying a flawed template. In business, a highly motivated sliver of the population can make you wildly rich. In politics, you generally need 50 percent plus 1, and, so long as they vote for you, their level of commitment is irrelevant. Until Trump, it was generally believed that America’s two-party system had the effect of moderating candidates, almost to the point of making them boring, because the incentives were for mass appeal.
But Trump’s bizarre campaign decisions go far beyond his offensive rhetoric. On any given day, Trump chooses to zig when any smart strategist would say to zag. Seriously, if you were to approach some of the top political advisers in the political business with a theoretical decision—say, ask a Karl Rove or a James Carville about a given political choice—nine times out of 10, Trump’s gut instinct would lead him to do the exact opposite of what they advised.
And because Trump miraculously won the election in 2016, and we all suffer from a recency bias (not to mention a bias against being made to look like fools again by underestimating him), there’s a temptation to think Trump has some masterful, if counterintuitive, insight. And maybe he will prove to be miraculous once again. But the notion that the so-called experts are playing checkers while Trump plays three-dimensional chess just doesn’t comport with the fact that Rove and Carville both got their principals re-elected, while Donald Trump appears to be headed toward bunking down with Jimmy Carter on One-Term Island.
If that happens, we will look back and conclude that 2016 was a fluke. Trump lucked into threading the Electoral College needle. Hillary was a historically bad candidate. We may be just 17 days away from conventional wisdom turning to: “Of course he lost! It was always so obvious. He never had a chance!”
Again, though, we’re left with the question: Why does Trump go against what should be in his own best interest?
I have theories. For one thing, Trump’s “gut” has been proven right in the past. Look at it from his standpoint. If all the so-called experts told you you couldn’t do something, and you did it, why would you listen to them? You might even convince yourself that you have the Midas Touch—that you’re on a mission from God.
Here’s the thing, though: The sample size is really small. I know Trump has skated by a lot in his life and in his business career (daddy’s money helps), but, in terms of politics, he’s just 1-and-0.
He has won just one election. All his other political “successes” these last four years have been subjective; he wins because he says he wins or because he acts like he wins. Politics is one of the realms where perception is reality. That’s why it’s so different from sports. In sports, sometimes the worst team in the league actually does beat the best team, because of some fluky play. But the aura doesn’t last long if, one week later, the bad team loses and the good team wins. Outside of politics, I can’t think of another domain where a fluke could make you a winner, and where your status as a winner couldn’t be empirically challenged for four whole years.
Former NFL coach Bill Parcells says, “You are who your record says you are,” and (for now) Trump has a winning record. Instead of breathing a sigh of relief and practicing hard to win the next big game, though, Trump took his victory as a sign that he deserved it. One problem with believing your own spin is that you fly too close to the sun and (ironically) arrange for a future failure.
A necessary part of this recurring story involves the principal being surrounded by “yes” men. Trump has always had sycophants, but in recent years, he has exiled anyone who dared tell him the emperor has no clothes on. Rex Tillerson, James Mattis, H.R. McMaster, they’re all long gone. If you want to rise in the ranks, the message is clear: tell Trump what he wants to hear—which is mainly that he’s awesome. What a dangerous environment for any leader to foster and cultivate.
One man’s confidence is another man’s arrogance. Often, the things that make someone successful (like chutzpah) guarantees their inevitable defeat (like hubris). If Trump loses, he will serve as yet another cautionary tale. The story keeps repeating. Someone audacious surprises everyone, but his reach exceeds his grasp, and he is humbled.
History is littered with the corpses of such men. It takes a lot of moxie to roll over your enemies. But then you end up in Russia, stranded in the snow, in the dead of winter. And winter, indeed, is coming.
