The Thing About Trump

Despite his reputation as a deal-maker, Trump has not in fact closed on very many big deals. His money, to the extent that we know anything about where his money actually comes from, has largely been made in branding deals, in selling Trump. The Apprentice, the success that he rode to the White House, is the culmination of this trend. It’s difficult, of course, to discuss his real estate transactions with much specificity, given how little is publicly available about them. But we know, actually, a far amount about the biggest deal that he was a part, one that I think tells us a lot about who he is and how he will govern and one that was a failure that almost destroyed him.

The deal was the creation of “Television City,” Trump’s plan for the land in western Manhattan that is now being turned into Hudson Yards. He had acquired it from the city in the 1970s, and it was clear even then that the plot was destined for development. When he was convincing banks to lend to him so he could throw money at Atlantic City and Trump Shuttle and all the rest of his 1980s extravagance, a big part of his pitch was the future payout he would make from Television City. Heck, even the land itself, undeveloped, was worth a fortune.

Building something on it, though, was not as straight-forward as building a skyscraper or a casino, and building either of those is incredibly difficult. The West Side property would require buy-in not just from the city but from local community leaders. This is why property development takes so long, even on property that is clearly ripe for development: as projects increase in size, the number of stakeholders that could frustrate progress grow exponentially, and developers need to be willing to play a long game of careful politicking and coalition-building to get anything done. It requires a steady, deft hand.

Trump, you will not be surprised, could not do this.

He fought with the local community, he fought with the city. He threatened and cajoled and went to court, and ultimately had to sell off the land in a desperation move, for cents on the dollar, in order to save the remains of his empire from the banks that had started to call in their loans. Trump was not able to take the long view, to suffer small losses in the pursuit of a larger goal; in the gom jabbar of big business, Trump jerked his hand back.

Whenever someone suggested that they wouldn’t do what Trump wanted, he responded not by seeking compromise or accommodation, but by attempting to browbeat them into compliance. This is a strategy that sometimes works (especially on people who view themselves as weaker than Trump), but when it fails leads his counter-parties to become increasingly entrenched in obstinate refusal to go along. And so the fights in the tabloids with the Mayor and with activists lead to a complete impasse, where the only way that the land could be developed was for Trump to sell and someone else to come in and develop relationships that he could not. This was essentially what happened, and Hudson Yards is one of the biggest Manhattan property developments of all time. Had Trump been able to pull it off, he would actually be a multi-billionaire, not just someone who plays one on TV.

The parallels between Television City and Trump’s presidency are too obvious to lay out in detail, but suffice it to say that “generating buy-in for complex projects from multiple diverse stakeholders” is a pretty good pocket summary of what successful Presidents actually do. An interesting contrast to Trump with regard to this skill is his predecessor, Obama: in this, as in so much else, they are mirror images, identical but completely reversed.

Trump wants, above all, to Win. He cannot stand to lose, not at anything. Ironically, it is this drive to victory at all costs that lead to his failure with Television City: although he may have “won” each interaction with his counter-parties, the cost of the victories was a step-wise movement towards gridlock. Obama, on the other hand, takes the long view to a fault. He focuses in on a long-term goal and then disregards small, short-term set-backs as irrelevant. Although long-term certainly is admirable, this strategy made it difficult for Obama to maintain the coalitions that he needed for his projects; as the short-term losses mounted, Obama looked increasingly aloof and out of touch as he pointed to some future pay-off. Obamacare on particular suffered from this method of governance, where every problem — premiums rising, insurers pulling out of the Exchanges — was dismissed as merely transient and sure to disappear once the program “really” started working.

It doesn’t require us to embrace the nihilist view that perception is reality in order to agree that perception plays a role in shaping reality. Many of Obama’s failures can be traced to his obstinate refusal to manage perceptions, which left him playing the long game all by himself. Trump’s failures are a result of his inability to see that anything other than perception shapes reality, and his concomitant inability to accept short-term losses in the service of a long-term goal. We can see this already, in his efforts to gain “victories” over Mexico and China, that play well to his base but also have the potential to be the first steps towards a disastrous trade war and a cataclysmic shooting war, respectively. We can only hope against hope that despite all appearances, Trump learned a lesson somewhere and has a long-term plan.