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#4 Kurt Angle
On the road to WrestleMania 18, Vince McMahon teamed up with Kurt Angle on an episode of SmackDown. Triple H, who was a babyface at the time, aligned with Flair to take on McMahon and Angle.
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A hard-fought battle didn't end well for the babyfaces. Undertaker came out in the end, just as Flair was about to connect a Figure Four on an unconscious McMahon. Taker hit a devastating Big Boot on Flair, and put Vince's body on top of him. This was enough for a three-count, and Vince managed to get a victory for his team.
Also read: The Fiend wrestles a Handicap Match after SmackDown Live goes off air
#3 Trish Stratus
As WrestleMania 17 was looming closer, Vince McMahon's rivalry with his son Shane McMahon was reaching a boiling point. McMahon met Shane in a Street Fight at The Grandest Stage Of Them All, in a losing effort. A few weeks before their big 'Mania match though, McMahon faced his daughter Stephanie in a Tag Team Match on an episode of Monday Night Raw.
Exactly a month before McMahon announced that he had bought off WCW, he teamed up with Trish Stratus to take on Stephanie and William Regal in a TV match. The match didn't end with a clear winner though, as Vince turned on Stratus and the trio embarrassed her in the middle of the ring to end the segment.
