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Bonus Watch '14: Investment Analyst Turned Fantasy Sports Team General Manager

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Fairy tales can come true, it can happen to you, if you quit your Wall Street gig and make some shrewd calls re: Eli Manning and Marquess Wilson.

Drew Dinkmeyer was a 31-year-old investment analyst when, two years ago, he decided to do something that most people would consider clinically insane: He quit his job in finance to play fantasy sports for a living...It turns out that Dinkmeyer wasn’t crazy at all. At the time, he said, he was already making as much money playing fantasy sports as he was in finance. That hasn’t changed since his side job became his full-time job, he says. He also just hit his version of the jackpot. Last week, along with more than 100,000 contestants, Dinkmeyer entered a football tournament hosted by the DraftKings daily-fantasy site—and Dinkmeyer won first place. The prize: $1 million. “I’ve had profitable years in both baseball and basketball so far,” he said Tuesday, “and now football is going to be a hugely profitable year.”

Dinkmeyer entered 49 teams into last weekend’s “Millionaire Maker” tournament. Each entry cost $27 for a total investment of about $1,300. For the 44th of his 49 teams, Dinkmeyer drafted New York Giants quarterback Eli Manning and wide receiver Odell Beckham Jr., a combination that combined for six touchdowns on Sunday, much to Dinkmeyer’s surprise. Manning had never worked out for him in the past. “It has been a disaster,” he said. “For years, I’ve been afraid to use him, because I don’t feel like I have a good read on him.” His team then shot up the standings on Sunday night when Dallas Cowboys wide receiver Dez Bryant caught three more touchdowns. That bumped Dinkmeyer up to second place overall with one player remaining on Monday and inspired DraftKings to send Dinkmeyer, an industry expert, to the W Fort Lauderdale hotel for a live Internet broadcast known in the daily-fantasy world as a “sweat show.” That meant the camera was there for Dinkmeyer’s reaction during Monday’s game between the New Orleans Saints and Chicago Bears. It captured the stunned look on Dinkmeyer’s face in the fourth quarter, with the Bears down 24-0, when Chicago quarterback Jay Cutler threw a one-yard touchdown pass to Marquess Wilson—who happened to be the last guy on Dinkmeyer’s roster. A completely inconsequential play in an otherwise meaningless game had just won him a seven-figure pay day.

How a Full-Time Fantasy Sports Professional Hit the Jackpot [WSJ]