The beloved TNT broadcaster is also a lifelong Cubs fan who threw out the first pitch and led Wrigley Field in singing "Take Me Out to the Ball Game" in June. This is a man who worked the NBA Finals after undergoing eight days of chemotherapy, so he's definitely not afraid of a curse.
His son, Craig Sager II, posted what appears to be an except from Sager's upcoming book, Living Out Loud. It revealed he placed a $1,000 bet on the Cubs to win the 2016 championship, a tradition he has kept up since 1981.
Through a long rebuilding period in the Windy City, Sager stayed positive and hoped for the best. The Cubs rewarded his loyalty by besting the Cleveland Indians in an instant-classic Game 7 on Wednesday night.
Because of his positivity, he can splurge on a nice new suit.