GOP Operatives Aren't So Sure That Trump Even Wants To Win

The Republican nominee's recent antics suggest that he's looking for an exit.
Donald Trump has confounded members of his own party to this day.
Donald Trump has confounded members of his own party to this day.

What used to be a playful question tossed around by Republican operatives about Donald Trump’s presidential campaign is now being taken far more seriously: Is it possible that he is trying to lose?

The notion, on the surface, seems preposterous. What politician would put himself through the crucible of a presidential campaign with the hope of falling short? But as Trump has stumbled badly on the trail and in the polls, and as his reaction to both has proven increasingly erratic, the theory of self-sabotage has gained traction among Trump critics.

“I think he has psychologically collapsed and is both consciously and unconsciously looking for an exit,” said Rick Wilson, a longtime GOP operative who rarely holds back in his disdain for Trump.

“It’s either that [he’s trying to lose] or it’s complete and utter incompetence in every facet of his campaign,” said Brian Walsh, another veteran Republican hand and Trump critic. “When you look at how he’s conducting every aspect of the campaign it seems entirely fair to ask if he’s purposefully trying to lose because the only alternative answer is complete arrogance and incompetence. And I’m not ruling out complete arrogance and incompetence.”

The sense that Trump desperately wants to avoid the responsibilities of being president hasn’t been plucked from thin air. Rather, it’s been fueled by a series of decisions made by both Trump and his campaign that have left even favorably disposed operatives baffled.

Trump reportedly raised $80 million in July. But he brags about not having run television ads and a Democratic ad tracker said his frugality extends to the radio airwaves too. He’s campaigned in places where he stands little chance of winning and been slow to open offices in critical battlegrounds. He’s insisted he can “act presidential” but has refused to do so. He’s forsworn campaign-like tours in favor of big rallies followed by flights back to New York and nights in his own bed. And recently, on the trail, he told supporters he didn’t want them to donate to his campaign.

His closest advisers are his children. But they have been traveling during these critical weeks. (His daughter, Ivanka, is currently vacationing with Vladimir Putin’s rumored girlfriend Wendi Deng ― a jaunt to Croatia that suggests a complete disregard for the optics of being too cozy with the Russian strongman.) 

And then there’s the state of the rest of his staff.

“That’s the thing that bothers me. So let’s suppose he is a smart businessman, just for this argument’s sake. He has marketing and communications and advertising and finance people in his resort, golf courses, real estate ventures and other things. He moves almost none of them over, save a lawyer and a digital/policy guy, both of whom are unhinged?” said Rory Cooper, who was a top operative to former Majority Leader Eric Cantor.

He noted that Katrina Pierson, a Trump spokeswoman, has what could most charitably be described as a difficult relationship with history and a strong penchant for hyperbole. “I just don’t believe he doesn’t appreciate the need for help. Yet he hires nobody, and when he does bring on anyone who knows their field, they’re gone in weeks,” Cooper said.

There is mass confusion within GOP circles about why Trump continues to employ Katrina Pierson, a spokeswoman with a penchant
There is mass confusion within GOP circles about why Trump continues to employ Katrina Pierson, a spokeswoman with a penchant for telling falsehoods.

Trump’s campaign didn’t return a request for comment. Sources close to him say the enormity of winning has indeed weighed on him ― as it would on anyone else. But they also note that his candidacy has been unconventional from the beginning, often by design.  

One oft-repeated story, several people have told The Huffington Post, is that upon entering the race, Trump told his campaign team that he didn’t expect to win the primary, anticipating instead that he would finished second or third and the publicity of a run would boost his business ventures.

Associates say that isn’t true. They expected to trail the top tier of Republicans during the early stages of the primary and make a big push as voting neared, relying, if need be, on Trump’s personal resources. What caught them off guard was both how quickly he moved to the front of the pack and how reluctant his fellow Republicans were to go after him once he was there.

When explaining the current state of the campaign, these associates point to that relatively bruise-free primary ― not some nascent desire to extricate himself from the path to the presidency ― as a contributing factor.

“No one really went out and attacked Trump during the primary season, for the most part,” said a source close to the Trump campaign. “And if you look at this reaction when his poll numbers did slip, when Ben Carson showed strength in Iowa, Donald Trump did the belt buckle speech and Carson didn’t really push back. The difference now is it is much harder to take down Hillary Clinton with one speech.”

While Trump may be unaccustomed to ― and rattled by ― sustained attacks from a political opponent, it remains unclear why he hasn’t adjusted his tactics amid evidence that those attacks are taking a toll. The aforementioned source argued that Trump has been let down by his aides. “Nobody is naive enough to think this campaign is going well,” the source said. “The fundamental problem is that the people now running this campaign don’t give a shit if he wins or loses.”

Nobody is naive enough to think this campaign is going well. The fundamental problem is that the people now running this campaign don’t give a shit if he wins or loses. A source close to the Trump campaign

But Trump’s Republican critics say blame lies with the candidate himself. One Wall Street-based GOP fundraiser referred to Trump as “an immature, juvenile, self-indulgent narcissist” who “wants to win but as an adolescent has no impulse control.”

“It’s not self-sabotage,” the longtime fundraiser said, “it’s self-delusion.”

Others, with less biting adjectives, echoed the idea that, far from trying to lose the election, Trump has proven psychologically incapable of winning it.

“When it turned out that he in fact won, and had to have a different strategy for a general election, he was not ready for it and his entire candidacy is not really premised on it,” said Avik Roy, a top policy adviser to Mitt Romney’s 2012 campaign and a senior adviser to Rick Perry’s 2016 campaign. “It was an intentional strategy on his part to exploit free media, and by being unpredictable and unscripted that they would cover him. He understood that. That was a strategy. And it worked in the primary but it won’t in a general, where people are saying, ‘Wait, this guy can be president.’”

In recent weeks, as his polling numbers have dipped, Trump has begun hinting that he knows he will lose ― whether he wants to or not. Complaining that the election will be rigged implies that he anticipates a Hillary Clinton win. Lashing out at the media for its coverage, and attacking his Republican detractors, show he's clearly searching for a scapegoat. He’s even openly discussed what he will do as a private citizen after the election ― the type of hypothetical no typical candidate would ever discuss.

It all portends an inglorious end to an improbable campaign, whose underlying purpose and goal will probably confound people long after it’s over.

“Just when I’m convinced that all signs of control of Trump’s actions point to Moscow, I’m jerked back to reality that only Bill Clinton could really devise this madness from a GOP nominee,” said John Weaver, who spearheaded John Kasich's presidential campaign. “Seriously, even someone trying to throw the race wouldn’t go to these lengths, even out of self-respect.”

Editor’s note: Donald Trump regularly incites political violence and is a serial liarrampant xenophoberacistmisogynist and birther who has repeatedly pledged to ban all Muslims ― 1.6 billion members of an entire religion ― from entering the U.S.