Donald Trump Is Trying To Lose

"If I don’t get there one way, I’m going to get to Pennsylvania Avenue another."
09/30/2016 04:16 pm ET Updated Sep 30, 2016
This is where it ends...
This is where it ends...

Several months ago, my dad and I were walking along Pennsylvania Avenue where we took a selfie in front of the White House. As it always does these days, our conversation turned to Donald Trump.

As we strolled a bit farther down the street, we came across the scaffolding surrounding what will become Trump’s latest project — a new fantastic, wonderful, hotel that is beautiful and that people will really love, believe me.

It was then that I could picture it. This is where it all would end. Trump would stand in front of a microphone (a fully operational one, not one of those defective ones the deceptive mainstream media gave him during the first debate), and say that, while he didn’t win the presidency, he would still have a great room on Pennsylvania Avenue. (Full disclosure: I thought/hoped this would happen a lot sooner than November.)

In front of that hotel, my dad (who is in real estate, and has been a Trump-observer for decades) repeated a theory he has clung to since the day Donald announced his candidacy.

“I don’t think he really wants to win. He just wants the attention and the fame. Not the job.”

While this is certainly possible, I’ve always assumed that at some point, Trump turned a corner and really wanted his next office to be Oval.

But my dad insisted, over and over, “He doesn’t want to win.”

So let’s posit a theory. The man who talks about nothing but winning actually wants to lose.

It explains everything. He refused to practice for the debates. He makes gaffe after gaffe. He doubles down on the worst parts of his performances. That’s crazy if you want the White House. But it’s genius if you want the headlines. All press is good press. It’s the perfect plan if your personal dopamine hit is seeing your own name in the headlines, day after day.

Remember all that sniffing during the debate? He was snorting Donald Trump.

You can say a lot of negative things about Trump. But one thing you have to admit is that he is the master self-promoter in the age of self-promotion. Kanye West thinks he needs too much attention. He has figured out a way to put his name on buildings he doesn’t fully own. He is the most famous rich guy who isn’t even that rich. And in the last year, he has become the most talked-about human in the world.

And that’s just what he set out to become.

You can say that Daddy gave him the money to start the real estate business. But he built his personal brand with smoke and mirrors of his own making.

It’s obvious that he never thought he could get this far. And everything makes sense if you accept that he doesn’t want to get any farther. You really think the master media manipulator of our era couldn’t do better in a debate than that schlub who showed up on Monday night? Every bit of evidence we’ve seen over the past few decades suggests otherwise. Donald kills on reality TV. He kills on Howard Stern. He kills every time he is trying to sell the one product he really cares about: Donald Trump.

Not buying it yet?

Well, consider the most important and unexpected line of the first debate — one that the pundits glossed over or completely ignored. It was his comment about that same hotel in DC:

We’re just opening up on Pennsylvania Avenue right next to the White House, so if I don’t get there one way, I’m going to get to Pennsylvania Avenue another.

If I don’t get there one way… In other words, if I lose. Remember, this is a guy who’s main selling point from the earliest primary battles was that he is winning. Why, at the biggest moment and on the biggest stage, would he mention his plans in the event he loses?

Think it was just a slip? Sure, maybe the most media-savvy self-promoter of our era accidentally said he might lose…

Or maybe my dad is right. Maybe that’s been the plan all along.

He gets the fame. He’ll continue to get the media attention. And he’ll crush one of the most famous adages we have: Everyone will remember who came in second place.

He hasn’t pivoted towards the center in the general election. He hasn’t spent much of his own money on ads. He hasn’t built a big ground operation. He won’t listen to advisors who tell him to brush up on the issues or prepare for debates.

And he’s spent the entire general election saying things that would have completely destroyed any traditional campaign.

And there’s the rub; the one thing that’s surprised so many observers and probably Trump himself. And the thing that is by far the most depressing and troubling element of this whole sick moment in American history.

He’s trying to lose. But the voters won’t let him.

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