Aired: 9/3/2020
The story of ophthalmologist Steven Friedlander who won a long-shot bet in one of the most dramatic Kentucky Derby races ever, only to find out the incredible payout wasn’t at all what he anticipated.
Aired: 9/10/2020
The story of a diehard Cincinnati Bengals fan sleeping on his roof until the his team wins a game.
Aired: 9/17/2020
A special education teacher enjoying a spectacular winning streak of March Madness picks, but haunted by his unorthodox betting style.
Aired: 9/24/2020
A last-place fantasy football loser forced to take ballet class as punishment, where he meets a classmate who changes his life forever
