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He was supposed to be the next major figure at MW. Had big star power in his fight against Romero, great social media game, and then it seemed like he never recovered from the Izzy loss.

Nate Diaz has to be up there. Inexplicably became one of the biggest stars in the sport in his early 30s after twenty-something fights in the UFC, and used his newfound leverage and bargaining power to fight five times in the next six years. Really striking while the iron was hot, so to speak
He left more money on the table than any guy i can think of though. He fought for 40/40 for years and suddenly through sheer chance he was making real money. If someone gets a huge raise and stops going to work you would correctly say they dropped the ballThis thread is about fumbling their career..
Nate made ~$15 million on his two fights against McGregor, then against Pettis, Masvidal, Edwards, and Ferguson, he still had by far the biggest paydays of his career, not even winning, as a 35 yo non-title contender, while not having to cut weight to make 170lbs.
I’d say he made out pretty well.
He left more money on the table than any guy i can think of though. He fought for 40/40 for years and suddenly through sheer chance he was making real money. If someone gets a huge raise and stops going to work you would correctly say they dropped the ball