The 18-year-old quarterback’s arrival represents the culmination of a $12 million NIL deal that involved an unlikely alliance between Oracle’s billionaire co-founder Larry Ellison, seven-time Super Bowl champion Tom Brady, and Barstool Sports founder Dave Portnoy to sway the teenager to move to Ann Arbor instead of Baton Rouge, La., and join the Wolverines.
“They said, ‘Hey, there’s this donor who wants to talk to you.’ I said I’m doing this by myself, and I don’t need to talk to anybody. And they said, ‘Please, this woman is a big fan of Barstool and you; she’d love to talk to you. Her name is Jolin,’” Portnoy recalled.
Brady, Michigan’s legendary former quarterback, played a crucial role by establishing a personal relationship with Underwood through regular FaceTime calls. The recruitment also featured an unexpected cameo from Connor Stalions, the former Michigan staffer who resigned amid the 2023 sign-stealing scandal. Stalions had joined Underwood’s high school coaching staff as a volunteer assistant, adding another layer of Michigan influence to the quarterback’s daily life.
