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#4 Jeff Jarrett
Jeff Jarrett has had a whirlwind relationship with Vince McMahon. Jarrett was signed by the WWE Chairman in 1992 and went on to become a popular mid-card heel, before leaving WWE in 1996 for WCW and then returning once again to the company a few years later.
After McMahon bought WCW, Jarrett was released from his contract, following which he founded TNA - a promotion to rival WWE. Jarrett was with TNA for over a decade before resigning and then returning twice to the promotion, which was later renamed Impact Wrestling.
Jarrett was then entered into a rehab program by WWE and Jarrett's wife Karen in 2017, after being found drunk ahead of an indie show.
Vince McMahon and WWE decided to help Jarrett despite the acrimonious way that the relationship between Jarrett and McMahon ended. This stems back to when he left WWE for WCW the second time, when he apparently asked McMahon for a huge payday to job to Chyna, which McMahon agreed, while he was also helping a former rival.
Jarrett was inducted into the WWE Hall of Fame in 2018 and then became a backstage producer in 2019, while he was also a part of the 2019 men's Royal Rumble match.
