

A unique point of view on sports history — reliving it through the lens of a sports bet. In each episode, ESPN’s Mike Greenberg sits down with a different bettor and hears the upbeat, fun, and comedic tales of bets with high stakes and unbelievable consequences.

Sep 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.

Sep 10, 2020
The story of a diehard Cincinnati Bengals fan sleeping on his roof until the his team wins a game.

Sep 17, 2020
A special education teacher enjoying a spectacular winning streak of March Madness picks, but haunted by his unorthodox betting style.

Sep 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