To illustrate just how drastically WWE has fallen, in 1998, Mick Foley led the Time Man of the Year poll. He was removed from consideration - it was felt that he hadn't "done enough" to warrant consideration, but clearly, his unseemly profession had much to do with it. Foley wasn't even the Man in 1998; wrestling was just that white-hot.
To be the Man, you don't beat the Man.
A passing of the torch is just another of pro wrestling's endless fictions. Very rarely does it happen; it was attempted, in 1990 - though Hulk Hogan treated the torch like it was a trillion dollar bill - when the WWF attempted to make the Ultimate Warrior the Man by foregoing the traditional transition custom. It was an audacious but unsuccessful gambit; Warrior didn't have the same working magic, he "wrestled" his old Intercontinental Title rival to diminished returns, and he just wasn't Hogan. So what does make the Man?
It's a combination of factors: drawing power, in-ring skill, the underrated ability to perform as a TV star, the ability to get oneself over, the ability through promos to sell big matches on the pape.
It, simply, is a matter of who was the biggest f*cking deal...