8. Brock Lesnar's Contract
In 2004, the then-WWE golden boy, Brock Lesnar (who was never a fan of the WWE travel schedule), informed Vince McMahon that he wanted to leave and try to start a career in the NFL (a dream which he almost realised). Vince, reluctantly, agreed, but one of his stipulations was that Brock couldn't wrestle anywhere on the planet or take part in MMA for any company for the next 6 years. Brock had two responses to this: 1) When he didn't quite make it to the NFL he began appearing for New Japan Pro Wrestling, knowingly breaking his non-compete clause and drawing a lawsuit from the WWE; and 2) He counter sued WWE, stating that it was unfair that they were denying him the opportunity to make a living for that many years (despite the fact that he was wrestling for NJPW). After a little bit of back and forth - including WWE discussing a potential return in 2005 - the court cases were dropped in mid-2006 and he was free to live as he pleased. Brock went on to become UFC Heavyweight Champion and returned to WWE in 2012 to a hero's welcome and a lucrative yearly contract with minimal performance dates. I think it's safe to say that Brock had the last laugh in this instance.