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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Baseball
Apr 12, 2026
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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
Mar 15, 2026
13 min read
“Even though he was one of the best pitchers of his era, he seems remarkably unknown.”
Mar 8, 2026
How he turned a $4,000 contract into a Hall of Fame baseball career.
Mar 1, 2026
The impact sent a jolt through his body as he collapsed to the floor...
Feb 22, 2026
What the average fan doesn't understand. PLUS: how he tore a hamstring on a strike 3 call...
Basketball
Feb 15, 2026
“There’s just no way any other college basketball game had this impact.”
