#2 Ric Flair
Following the end of the Monday Night Wars with WCW, where WWE ran victorious, Ric Flair made his return to Vince McMahon's promotion in 2001.
Upon arrival, he was embroiled in a feud with Vince himself as The Nature Boy claimed to be the half owner of WWE. Shane and Stephanie McMahon had apparently sold their shares in order to purchase WCW and ECW and their stake was now owned by none other than Ric Flair himself.
An irate Vince McMahon booked a match between the two at Royal Rumble 2002 which Flair won. Eventually, Vince would control SmackDown while Ric Flair took over Monday Night RAW.
To decide who would have complete control over proceedings, Vince McMahon and Ric Flair took part in a No Holds Barred match on the 10 June 2002 episode of RAW.
The Nature Boy was busted open during the encounter but managed to lock in the Figure Four Leglock on Vince McMahon after a few back-and-forths. It was then that Brock Lesnar would interfere and deliver the F5 on Ric Flair. Vince would then get the pinfall and gain complete control of WWE.