Trump Wins By Wearing You Down

And a whole party has adopted the strategy.

Will Leitch

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Maggie Haberman’s essential, definitive Donald Trump biography Confidence Man is full of never-heard-before anecdotes and subtle, smart insights about the man, all delivered in a relentlessly readable package: I suspect of all the Trump books, it’s the one that will stand the test of time. (Unless he becomes President again, in which case he’ll probably just end up banning it.) But there’s one moment in the book that I speaks most powerfully to our current moment, specifically the midterm elections, which, increasingly, look like they’re going to go Trump’s and the Republican’s way.

It’s early on, when Trump was still just a cocky real estate bro trying to starting out and buying up high-profile real estate in Manhattan. He had long wanted to build on the Upper West Side side, specifically a section of rail yards that had been made available in a bankruptcy of a company called Penn Central. He’d lost the option to buy the yards back in 1979, but the option was still available, and everyone else had forgotten about it. But Trump hadn’t. And thus he used one of his superpowers:

While long-term planning was not in him, Trump was well-versed in the habit of obsessive thought, a continued private focus on something from which others had long ago moved on.

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Will Leitch
Will Leitch

Written by Will Leitch

Author seven books, including “How Lucky” "The Time Has Come" and "Lloyd McNeil's Last Ride." NYMag/MLB. Founder Deadspin. https://williamfleitch.substack.com

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