In 1985, Donald Trump bought West Side Yards*, a huge real-estate parcel on the West Side of Manhattan. (Actually, it was his second try at the property, which he’d failed to develop in the 1970s.) Trump paid $115 million to buy the parcel, with huge plans to create a sparkling center on one of the few remaining undeveloped parts of the island.
It didn’t work. Trump quarreled with Mayor Ed Koch, failed to start the work, and steadily lost tens of millions of dollars. In 1989, he declined an offer to sell the land for a more than $400 million profit. Five years later, he finally threw in the towel, selling it for just $82 million—and on condition that the buyer take on a quarter of a billion in debt. But Trump was right about the commercial potential of West Side Yards. The developers who bought the land from him sold it for $1.8 billion in 2005, the largest residential real-estate deal in New York history. A sparkling new neighborhood is finally rising on the site.
The point of this story is not that Trump blew the deal of a lifetime, though he did. The point is that from Trump’s perspective, who cares? Yes, he could have been richer; but he’s still extremely rich, his reputation as a business mogul remained unscathed outside of actual business circles; and, as he put it to Time this week, “I’m president, and you’re not.” Trump’s bounce back from the West Side Yards fiasco seems to be a useful key for understanding Trump’s approach to negotiations over repealing and replacing Obamacare.