26. Khalil Mack
Mack became the highest-paid defensive player in NFL history when he joined Chicago in 2018. However, the road to Chi-Town was a grueling one after an intense contract holdout. He missed the Raiders’ entire preseason program because he wanted a lucrative extension.
This was also a defining moment in the NFL because it signaled a new age of player power. Oakland didn’t want to trade him but he didn’t leave them much choice. Mack didn’t care about leaving his teammates high and dry because he wanted what was best for his career (via NBC Sports).