8. John Bradshaw Layfield (WWE Payroll 1996-2009 And 2011 - Present Day)
In terms of personalities being close together, Vince McMahon and John Bradshaw Layfield are the ultimate pairing. Both are brash and intelligent, both have a love of toughness and both are passionate about finance. They even have the same sense of humour and that's partly why Bradshaw got away with so many 'hazing' jokes in the late 90's. Bradshaw quickly earned Vince's trust by demonstrating his loyalty to the WWF as the enforcer of backstage's 'Wrestling Court'. In this role Bradshaw made sure younger talent were respecting the WWF brand and history, he was the embodiment of Vince amongst the boys. McMahon appreciated this and in 2004 hot-shotted Bradshaw into the role of WWE Champion, after Brock Lesnar had left Smackdown high and dry of a number one heel. That's why loyalty matters to Vince, someone like Lesnar he can't count on, but JBL was a reliable act he could turn toward. You need people like that in a company, not necessarily the greatest wrestler, but someone who will always go out and bat for you come rain or shine. Bradshaw did leave the WWE briefly in 2009 to heal up a badly injured back, but he has now returned to the company as a commentator, a position he is proving excellent in. A near two decades of working for Vince looks set to continue far into the future.