I’ve got history with this guy. I’ve been losing money on Floyd Mayweather, Jr. for years. I am a phenomenal sucker who bets against Floyd every chance I get. I’ve never once believed that he will lose a fight, and on that score this upcoming bout with Victor Ortiz is no different. But I always hope he will lose. My reasons why are embarrassing and have nothing to do with boxing, this sport that I consider myself a fan of.

Floyd is a villain, a contemptible person. He changed his nickname from “Pretty Boy Floyd” to “Money Mayweather” and he takes great pride in flaunting his wealth. He burns hundred dollar bills. He belittles his opponents as homosexuals even long after he has beaten them. In the run-up to all of his fights he goes to great lengths to play the bad guy, and that’s truly what it is—playing. He is a promoter and an entertainer and admits as much. But I fall for it anyway. Despite the fact that Money Mayweather is as skilled a tactician in the ring as anyone fighting today I still root for his defeat. A sucker play, sure, but in betting with my heart and not my head, I am at least in good company.

“$50 Under 11.5 Rounds Floyd Mayweather, Jr. VS. Victor Ortiz.” — David Hill, McSweeneys. Each of Hill’s columns tells a story of a single bet that he made.

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