Bettor Days

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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.

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Creators and Cast

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Episodes

Season 1

4 episodes

S1 E1 · Fauxto Finish

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.

S1 E2 · Danger: Caged Bengal

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

S1 E3 · Pocket Change

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

S1 E4 · Texas Two-Step

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

Season 2

8 episodes

There is no shortage of emotional highs and lows once you start digging into the world of sports betting,” said Greenberg. “We had so much fun hearing from fans during season one of the show, and this next collection of episodes offers many crazy, often hilarious, sometimes touching, often hard-to-believe tales of people who took a gamble and ended up with a terrific story.

S2 E1 · Monday Night Odyssey

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.

S2 E2 · Hip-Check Blues

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.

S2 E3 · Falcons and Waffles

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.

S2 E4 · Fear & Footy in Las Vegas

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.

S2 E5 · Gelato with a Kick

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..

S2 E6 · Just Win Brady!

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.

S2 E7 · A is for Astros

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.

S2 E8 · Max Madness

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.”