The Underdog Newsletter
The best sports stories you've never heard & powerful lessons from underdogs beating the odds.
Written by
Tyler O'Shea
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Basketball
May 31, 2026
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7 min read
"I'm not afraid to be the goat."
Football
May 24, 2026
6 min read
This 7th-round pick left the sport at his peak for something bigger.
May 17, 2026
8 min read
"Oh man, it was definitely the wrong call."
Baseball
May 10, 2026
He was one semester away from pharmacy school...
May 3, 2026
He didn't play a single second in high school...but now?
Apr 26, 2026
Here's how he became an NFL "super agent"...
Apr 19, 2026
He was a 5'6" high schooler who "couldn't make a layup". Here's how he became a Hall of Famer...
Apr 12, 2026
18 min read
Armed with borderline irrational self-confidence, he "bugged" his way into pro baseball.
Apr 5, 2026
14 min read
They doubted that he'd ever play again. Then he did the impossible...
