We are going old school for this entry on our list. Bruno Sammartino dominated the 1960s and 1970s, selling out Madison Square Garden 187 times. At the turn of the 1980s, however, his career was winding down. Bruno retired after he became aware that Vince McMahon Sr. cheated him out of percentages of his gates at MSG. Vince Jr. eventually settled out of court with Bruno and convinced him to come back and do color commentary for significant sums of money. Vince eventually convinced Bruno to return to the ring in 1984 to promote his son Davids career. Bruno would wrestle for another four years before retiring again for good.
