The Man Who Made $500,000 Off Trump’s Win

A mini-episode of Unorthodox with Bob Barnes, a Trump supporter who bet big on the Republican nominee

November 21, 2016

Hi, Unorthodox listeners, it’s Mark here. During this past election season, I had exactly one Facebook friend who was posting pro-Trump material. His name was Bob Barnes, and he was a guy I had gone to college with for two years. At Yale, in the mid-’90s, Bob was widely known on campus as the anti-elitist southern populist—tribune of poor, rural white folk, as it were. Although he had attended a private school (on scholarship), and was well-liked at Yale, he was always ambivalent about … well, about people like me: a preppy, a legacy, a liberal. Bob thought there were too many of me at Yale, and not enough of him, a point he made articulately, and forcefully, in campus publications. His politics were, in true populist fashion, both to the left of mine and to the right of mine. He hated elitists, including most conservatives. But he also hated liberals.

Anyway, he left in the fall of junior year, transferring to the University of Tennessee. I found the Yale Daily News article about his departure—here it is, from November 1994:

I always wondered what happened to him. We reconnected about six months ago—on Facebook, of course—and I discovered that he had remained a colorful character. He is a lawyer in Los Angeles, best known for getting Wesley Snipes an acquittal in his tax avoidance case a few years back.

Barnes is also something of a professional gambler. He guessed right on Trump, and when I reached him—for this special episode of Unorthodox—he was in London collecting $500,000 in winnings—Trump was getting 4-1 odds across the pond.

Related: Unorthodox

Unorthodox is a smart, fresh, fun weekly take on Jewish news and culture hosted by Mark Oppenheimer, Stephanie Butnick, and Liel Leibovitz. You can listen to individual episodes here or subscribe on iTunes.

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