DraftKings Is Coming for Your Dumb Money at Wrigley Field (1)

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 ...