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 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
7 min read
He didn't play a single second in high school...but now?
Football
Apr 26, 2026
6 min read
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...
Mar 29, 2026
15 min read
Benched in college, cut in the pros, he worked 5 jobs at a time on his way to the bigs.
Mar 22, 2026
How a 5'8" assembly line worker became an MLB legend
