On June 16, to his surprise, Jay Cutler arrived at the L27 rooftop bar at The Westin Nashville for his own retirement party. Unbeknownst to Cutler, his wife, Kristin Cavallari, had invited several dozen family and friends to a celebration of his football career and a sendoff to his next pursuit, a broadcasting gig with FOX Sports. Overlooking Nashville’s highest infinity pool and a sweeping view of the city below them, guests including Miami Dolphins head coach Adam Gase listened to Cutler as he thanked all those who had a part in his life in the NFL.
“I don’t know if I was convinced he was done,” says Gase, who coached Cutler as a coordinator in Chicago in 2015—arguably Cutler’s best season—before taking the head-coaching job in Miami in ’16.