41. Tom Brady
Technically this wasn’t a contract holdout in the traditional sense, but it was a massive story. Brady was synonymous with the Patriots for two decades. But he maintained a tense working relationship with head coach Bill Belichick. The pair treated each other with cold professionalism but didn’t have a close bond. Then Brady rocked the world when he refused to sign a new deal.
Instead, he opted to become a free agent and pursue a fresh start. It was a shock because nobody expected him to leave the Patriots after so long. Finally, he joined the Buccaneers and won another Super Bowl. It was a massive moment for his career because he broke many records and made a lot of money. Brady proved that he could do it without his former coach too (via AS).