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The Real-Life Happy Gilmore

Sep 14, 2025

•

15 min read

The Real-Life Happy Gilmore

How a self-taught rebel broke all the rules and became a legend.

Tyler O'Shea
Tyler O'Shea

Football

He Wasn't Invited

Sep 7, 2025

•

16 min read

He Wasn't Invited

But he showed up anyway...

Tyler O'Shea
Tyler O'Shea

Baseball

He Hit Every Dead End

Aug 31, 2025

•

17 min read

He Hit Every Dead End

But each one became a stepping stone to baseball glory...

Tyler O'Shea
Tyler O'Shea

Football

The 68-Year-Old Football Player

Aug 24, 2025

•

18 min read

The 68-Year-Old Football Player

EXCLUSIVE: World record holder reveals how he got back in the "Time Machine"...

Tyler O'Shea
Tyler O'Shea

Football

Thanks, You're Fired

Aug 17, 2025

•

15 min read

Thanks, You're Fired

They did the impossible...then got kicked to the curb.

Tyler O'Shea
Tyler O'Shea

Football

59-Year-Old College Football Player

Aug 10, 2025

•

12 min read

59-Year-Old College Football Player

His crazy story inspired a new Hollywood film...

Tyler O'Shea
Tyler O'Shea
His Toughest Fight

Aug 3, 2025

•

18 min read

His Toughest Fight

...happened outside the ring. Here’s how he learned the hard way.

Tyler O'Shea
Tyler O'Shea

Baseball

He Shouldn't Have Survived

Jul 27, 2025

•

13 min read

He Shouldn't Have Survived

How a near-death scare turned a mediocre D3 pitcher into an MLB flamethrower.

Tyler O'Shea
Tyler O'Shea

Football

He Was Homeless on the Streets of London

Jul 20, 2025

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14 min read

He Was Homeless on the Streets of London

“There were times I’d steal food just to eat.” You won't believe where he ended up...

Tyler O'Shea
Tyler O'Shea

Baseball

The Lazy-Eyed Legend

Jul 13, 2025

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8 min read

The Lazy-Eyed Legend

How a 20-year-old electric factory worker with a lazy eye became an MLB star.

Tyler O'Shea
Tyler O'Shea

Baseball

He Went From the Military to the Major Leagues

Jul 6, 2025

•

14 min read

He Went From the Military to the Major Leagues

Meet the 5'5" shortstop who went from the Air Force to the MLB's smallest player.

Tyler O'Shea
Tyler O'Shea

Football

He Drove a Dump Truck

Jun 29, 2025

•

14 min read

He Drove a Dump Truck

And played semi-pro football under a made-up name...just in case.

Tyler O'Shea
Tyler O'Shea
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The Underdog Newsletter

The Underdog Newsletter

The best sports stories you've never heard & powerful lessons from underdogs beating the odds.

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