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More than any public figure in recent memory, and certainly more than any major party politician of the modern era, Donald Trump loves to win.

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Winning—not just winning an election, but winning, in the Charlie Sheen/DJ Khaled sense of general excellence—has been the ideal at the core of Trump's public life. Calling someone a "winner" is the highest possible compliment in Trumpworld, and he's applied it liberally—not least to himself.

"My life has been about winning," he told Breitbart last month.

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"We will have so much winning if I get elected that you may get bored with winning," he told a group of supporters last year.

"Unless I win," Trump said last weekend, "I will consider this a big, fat, beautiful—and, by the way, very expensive—waste of time."

In my favorite paragraph ever written about Trump, GQ's Drew Magary outlined how central the concept of winning is to Trump's populist appeal:

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The whole thrust of The Donald’s campaign is that he is special. He is extraordinary. In Osky, he compared his business acumen to Jack Nicklaus’ golfing ability and Babe Ruth’s hitting ability. (“It’s called talent. Talent.”) He is a WINNER, and he is here to help this nation of sad losers learn how to win again.

“We don’t win anymore in this country,” he told the crowd. “When was the last time we won? When did we beat China in a deal? We don’t win.”

From an statistical perspective, Monday night's Iowa caucuses, in which Trump placed second to Ted Cruz, probably don't mean much. The Iowa caucuses have never been reliable precursors to victory in the GOP primary contest (just ask 2012 winner Rick Santorum, or 2008 winner Mike Huckabee). And Trump still has plenty of chances to win early primaries in New Hampshire, Nevada, and South Carolina, all states in which he has a commanding lead in the polls.

But on a purely emotional level, the loss has to feel particularly brutal for Trump's supporters. In the first voting event of the 2016 election, their candidate, a man who has been preaching the Gospel of Winning his entire career, who has been loudly Winning every poll and every debate and Twitter beef for the past year, and proclaiming himself the Winner who can Make America Win Again, did not, in fact, win.

Donald Trump may resume winning. But for a night, he's a loser. And for the Trump fans who have put their faith in him as their invincible winner-in-chief, the shock of seeing Trump try very hard to win something, and come up short, must be a major setback. Trump losing is like the Harlem Globetrotters losing—it's not supposed to happen. But Monday night, it did, and Trump's base will need to be convinced that it's OK for even a winner to place second sometimes.