#3: The Champion of the board
In 1999, Vince McMahon had a very strange year. Starting off, McMahon was embroiled in his classic feud with Stone Cold Steve Austin, that saw the Chairman shockingly win the Royal Rumble.
Later in the year though, the Boss would become a babyface, after being enraged by Triple H, who had married Vince's daughter Stephanie against her will. So sure he would beat the boss, the Game put his WWF Championship on the line, a costly mistake.
Though the young champion battered the boss for the majority of the match, McMahon would have glimpses of opportunity.
Ultimately, it was Steve Austin who made the difference, attacking Triple H from the crowd, neutralizing his henchwoman Chyna, and helping his former nemesis become the champion of his own company.