44. Jorge Masvidal
Masvidal became a global superstar in 2019 after he knocked out Ben Askren. His flying knee caused the quickest KO in UFC history. Meanwhile, Masvidal’s persona and image helped him to capture the love of fans. Even though he never won a title he was one of the company’s biggest draws. This was more important than winning fights because it brought money to the promotion.
But Masvidal wanted to see more zeros at the end of his paycheck. He demanded more from the notoriously tight-fisted UFC. They reacted in stubborn defiance but in the end, he got what he wanted. After begging the UFC to release him, he ended up with the contract he wanted. Somehow, he received the third-biggest deal in the promotion’s history (via Marca).