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Trump’s “winners and losers” mentality made him a hit on reality TV but a flop in the debates

Donald Trump wanted the debates to function like an Apprentice boardroom. Clinton wouldn’t bite.

Final Presidential Debate Between Hillary Clinton And Donald Trump Held In Las Vegas
Members of the media watch the third US presidential debate.
Photo by Justin Sullivan/Getty Images
Emily St. James was a senior correspondent for Vox, covering American identities. Before she joined Vox in 2014, she was the first TV editor of the A.V. Club.

Something about Donald Trump’s debate performances against Hillary Clinton has been bothering me.

At various points throughout the three debates, he’s turned to her and said, in effect, “Why didn’t you solve every problem in the US while you were first lady/senator/secretary of state?” In particular, he seems baffled by the thought that she would let someone like him get away with taking such massive tax write-offs.

On its face, this idea is pretty stupid. Even the earliest student of American government knows that the power of even the president is limited — to say nothing of the power of one senator out of 100. But Trump keeps returning to it, again and again.

Vox’s Ezra Klein has theorized that it might stem from Trump essentially believing politicians should have near dictatorial powers — something that would fit with his seeming appreciation for strongmen and tyrants. And that’s likely at least part of it.

But there’s something else going on here, something that speaks to a strategy Trump carried into the debates and spectacularly failed to execute: He wanted to turn them into a boardroom meeting from The Apprentice.

On The Apprentice, individuals were blamed for team failures

In and of itself, this idea sounds kind of nutty, I’m aware. It’s clear that Trump didn’t prepare too much for the debates — if at all — and it’s also clear that he was somewhat rattled by not having a loud, cheering crowd to play off.

And yet the way Trump phrases this question to Clinton at each debate, as if he’s baffled that she didn’t unilaterally end the free ride he received, as if he doesn’t understand how the legislative branch works, is essentially couched in the same language that he would use on The Apprentice when querying a member of the team that had lost that week’s challenge.

It’s been easy to forget, with the recent focus on Trump’s worst moments in that famed reality show, but The Apprentice was really entertaining TV, particularly in its early going. And it was entertaining TV for a good reason: Creator Mark Burnett and his team understood that the show would work best if Trump was a spice and the normal contestants were the meal.

Thus, every episode proceeded with two teams of potential Trump employees facing off in some sort of business-related challenge. Usually these challenges had something to do with marketing or branding, consistent with how Trump has made most of his money in the past couple of decades. One team would win. One team would lose. Somebody from the losing team would go home. Trump would make those calls in the boardroom.

Now, leave aside for a moment that a lot of this was decided in editing. What’s important is the way those boardroom sequences played out, especially once it was down to the losing team sitting with Trump. He would question them, pulling apart various flaws in their arguments (or, in later seasons, following his own capricious whims).

He would reward team players some weeks, then punish them the next. He would punish project leaders one week, then decide they weren’t at fault in another episode. But the important thing was that to Trump, the failure of an individual was the failure of the team, and vice versa. Once you were a loser on The Apprentice, that was what you were, until the next week.

Naturally, these boardroom meetings were heavily edited, but they also became by far the most popular thing about the show. And as their popularity grew, so did Trump’s.

How Trump tried to turn the debates into a boardroom meeting — and failed

You can see Trump pulling out this strategy in every single debate he’s been in, no matter how little sense it might make in the moment.

Clinton was part of President Obama’s Cabinet. And since Trump disagrees with much of what Obama has done, Clinton can not only be painted with the same brush — which is a totally fair political discussion point — but can be directly responsible for things that happened on Obama’s watch, even after she stepped down as secretary of state. Team becomes individual, and vice versa.

Similarly, Trump seems to view most political debates or geopolitical conflicts in terms of simple winners and losers. That’s been consistent across his political history, but it’s also not hard to contemplate a Trump who imagines himself in some sort of global boardroom, deciding which player on Team Obama is going to be fired for losing to Team Putin.

You can even hear this in the way Trump discusses how Iran or China or Russia “outplayed” the US. Everything becomes a game of this versus that, of nation versus nation, of us versus them. It, on some level, always boils down to two Apprentice teams against each other, with Trump himself getting to decide who won and who lost.

But the problem is that when you’re going to be the star of a reality show, you become incredibly dependent on your editors. Trump could get away with reality show–style attacks in the Republican debates because there were so many candidates. With so much going on, the sheer wildness of some of what he said could skate by unnoticed. In that sense, as I’ve noted before, he was playing a classic “not here to make friends” reality show villain.

But when you want to pivot in a two-person debate to being the ultimate arbiter, the final judge of who won and who lost — well, you’re not going to have great editors, because everything is happening live.

What you need, then, is somebody who is immediately cowed by your authority and decides to play the game on the terms you’ve set — one where there are winners and losers and somebody’s getting fired at the end of the episode. Clinton’s greatest strategic maneuver across 270 minutes of debates was to very, very rarely get drawn into this sort of discussion with her opponent, instead needling him with tiny stings and jabs, derailing him until even his Apprentice editors couldn’t have saved him.

I don’t want to make too much out of this. Trump’s “winners and losers” style of understanding business dealings, the world, and life in general stretches back to long before The Apprentice. (Trump’s ghostwriter Tony Schwartz talked about Trump thinking of everyone as “losers” or “the greatest” in Jane Mayer’s New Yorker profile.) But it was on that show where he learned to turn his understanding of the universe into good television, and it makes sense that he’d try to carry forward the same ideal into the debates.

That he didn’t succeed now seems inevitable — it’s a pretty risky strategy, all things considered. But there’s probably some alternate universe where his tactics worked, where Clinton got caught in the endless sorts of blame games that defined so many Apprentice boardroom meetings, and Trump smiled smugly as she dug her own grave.

But we don’t live in that universe. We live in the one where the world’s first reality show candidate finally spun out because he fatally misunderstood his own strategy.

Watch: Clinton's debates left the Trump campaign in ruins

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