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Illustration: Doug John Miller for Bloomberg Businessweek

DraftKings Is Coming for Your Dumb Money at Wrigley Field

The betting app wants you to root, root, root for a prop bet. If you don’t win, it’s a shame.

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On a sticky morning in June, Crane Kenney, the neatly pressed president of the Chicago Cubs, ushered a dozen reporters across the loose gravel of a construction site just outside Wrigley Field. “Slip-and-fall,” Kenney, a lawyer, teased a burly cameraman. “I can see it.” Standing beside Kenney, in wraparound mirrored sunglasses and a wide-collared blue gingham shirt open to the breastbone, was the corporate partner he’d come to celebrate: Jason Robins, co-founder of betting app DraftKings.

We were there to watch the two of them sign a steel beam that will eventually sit inside a two-story, Las Vegas-style sportsbook and bar. Robins’s company is paying the Cubs $100 million over 10 years for the right to operate it, according to a person familiar with the agreement. The glass-walled venue will be welded in several places to the stadium and stretch almost half its length near the intersection of Addison Street and Sheffield Avenue. Renderings depict signs flashing the DraftKings name and an L-shaped, 2,000-square-foot TV screen.