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Like fishermen and romantics, gamblers never forget the one that got away. For Rob Minnick, now 25, that was in 2018, during the annual “March Madness” college basketball tournament. Early in the competition, the underdog Retrievers of UMBC (that’s University of Maryland, Baltimore County) beat the favored Virginia Cavaliers in a massive upset. It was the first time in college basketball history that a 16th-seed team (for non–sports fans, that’s the worst, lowest-­ranked team in its geographical region) had defeated a first-seed favorite. And Minnick felt like an idiot for not having laid money on it. “Worse than losing a bet,” he says, “is not making a bet that you would have won, and feeling regret about it. I was like, ‘That was obvious,’ even though it had never happened before.”