#1 Bret Hart (20-year WWE contract)
To recap, Mark Henry and Randy Orton remained with WWE for their entire 10-year contracts, while The Big Show left the company two years before his long-term deal was originally due to expire.
In Bret Hart’s case, he was given a 20-year contract by WWE in October 1996 but he did not come anywhere close to completing that extraordinary deal.
Due to WWE’s struggles and WCW’s financial power, Vince McMahon was unable to honor Hart’s contract and he allowed his Superstar to negotiate a deal with the rival promotion in 1997.
This led to “The Hitman” leaving WWE to sign a contract with WCW that was reportedly worth around $3 million per year for three years.
Hart’s departure resulted in one of the most controversial moments in WWE history, and he admitted in 2020 on an episode of WWE Backstage that he wishes he never joined WCW.
“If I could do it all over again, I think I’d try to figure out a better way to stay in WWE. Knowing what I know about WCW, I’m sorry that I ever went there.”
Hart had problems with WCW producer Eric Bischoff during his time with the company, while he has repeatedly criticized Goldberg in recent years for hitting him with a botched kick that ended his career.