I didn't see the one where McMahon won but I would imagine the premise was that nobody went out, kicked his butt, tossed him in and then out again because he was the Boss and only a few like Austin would say "Who cares?" and do it anyway. But some of these guys were snatched from eras before Vince, Jr. even was the boss and will go back to those eras after the match so they don't care and will toss him in and out again. Heck, if Bruno is still in the match by then (unlikely, I admit), he would toss him in, beat on him for an hour and then toss him out since he really didn't like Vince, Jr.