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.

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

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

A last-place fantasy football loser forced to take ballet class as punishment, where he meets a classmate who changes his life forever

Rob, a die-hard football fan and avid ancient history enthusiast, settles in with his new puppy for a Monday Night Football match-up between the Bears and Rams. An improbable line-up he selected on his daily fantasy app propels him to first place, and a shot at $1,000,000.

Angie, a St. Louis native, lives for her hometown teams. While on a work trip to Vegas she places a few bets on her beloved Cardinals and St. Louis Blues. Her long shot wagers take her on a season long journey through ups, downs, and even hip surgery.

Michael finishes in last place in his fantasy football league after stacking his roster with players from his favorite team, the Atlanta Falcons. Now his friends are making him pay up. Hopefully he has the appetite to endure the challenge.

While on a trip to Vegas with friends, Bryson puts down $2500 on Manchester United. A mysterious man enters the sportsbook and Bryson’s bet takes an unfortunate turn from winning some cash to absolute trash.

Mike, who owns a Gelato shop, and his best friend Chris make an outrageous in-game bet that wins them $56,000 when Denver Broncos kicker Brandon McMannus hits a game-winning field goal, but their sweet victory melts away the very next day..

Figgy had never gambled in his life, but after the Patriots defeat his beloved Raiders in the infamous Tuck Rule game, he places a series of bets on then little-known quarterback Tom Brady, in the hopes of winning $30,000.

Vinnie is a pre-school teacher, comedian and an avid Houston Astros fan. After he makes a mistake while placing a bet on his favorite team, Vinnie realizes that he needs to learn his lesson or become the punchline of a miscalculated wager.

Max organizes a March Madness bracket pool with his friends. The problem? He’s 12 years-old. After getting caught the whole country learns of Max’s story, and even Jimmy Kimmel wants to hear from the “5th Grade Bookie.”