Vince McMahon and Triple H were one of the best heels to ever appear in WWE. Although both were great at generating heat, one was more of a cold, calculating character and the other was very vindictive. Both had their best moments as heels in WWE and they even crossed the line several times on live television.
But the biggest question is, who was the more evil of the two in WWE? Older wrestling fans will probably lean towards Vince but for newer fans, the answer might be Triple H. The following are a few examples of the most vicious acts these two did as heels and see who was better.
10 Triple H: The Katie Vick Angle
In 2002, Triple H got into a rivalry with Kane. The Game revealed the truth about Katie Vick, Kane's ex-girlfriend, who passed away in a car crash and told the fans what The Big Red Machine did with her after her death.
Triple H recreated the scene by wearing Kane's mask and then proceeded to crawl into the casket with the mannequin. This was one of the disturbing segments in WWE and they've been trying to hide it from the fans for years now.
9 Vince McMahon: Degraded Trish Stratus On Live Television
The controversial relationship between Vince McMahon and Trish Stratus was more bad than it was good. Not only did Vince make out with Stratus in front of his wife Linda, but he also degraded her on several occasions. He even once forced Trish to strip down to her skivvies and bark like a dog.
While this might seem very inappropriate for the younger fans, and it is, the storyline with Vince also changed Trish's career forever for the better.
8 Triple H: Tried To Take Out Steve Austin
During Survivor Series 1999, "Stone Cold" Steve Austin was almost killed after someone ran over him with a car. Austin missed almost a year worth of in-ring action. When he returned, The Texas Rattlesnake found out that Rikishi was the man who drove over him and he did it for The Rock.
But some time later, Triple H attacked Austin and revealed that he was the real mastermind behind this attack that almost killed the superstar. These two then faced each other at Survivor Series 2000 where Austin got his revenge.
7 Vince McMahon: The Kiss My Ass Club
Vince McMahon's Kiss My Ass club began in 2001. He literally made wrestlers kiss his buttocks and if someone denied, they'd either be suspended or lose their job in WWE. William Regal was the first member of this club.
The Rock finally put an end to this segment a few weeks after the angle started, when he made Vince kiss Rikishi's behind. After a few years on the shelf, McMahon brought the angle back for his storyline with Shawn Michaels in 2006 and the segment has happened several times since.
6 Triple H: Drugged & Married Stephanie McMahon
Triple H married Stephanie McMahon on-screen in 1999. But at that time, Stephanie was in an on-screen relationship with another WWE superstar named Test. The Game drugged her one night and then married her in a drive-through ceremony.
Although it was later revealed that this marriage was pre-planned by both superstars, the fact that Triple H even brought up the whole drug-angle on television was an unforgettable heelish move. It also set the stage for the shocking twist that Stephanie helped orchestrate the whole thing to get back at her father.
5 Vince McMahon: Openly Cheated On His Wife
While Triple H did some really terrible things on television, he still maintained a great relationship with Stephanie McMahon until 2002 when they divorced in a storyline.
On television, Vince McMahon was not faithful to his wife Linda McMahon. He was involved in a relationship with wrestlers such as Stacy Keibler, Torrie Wilson, Trish Stratus, and more.
4 Triple H: Made Racist Comments Against Booker T
Triple H and Booker T feuded over the World Heavyweight Championship. Their match happened at WrestleMania XIX but Booker T surprisingly lost. After all the buildup where The Game made racist remarks against Booker several times during the buildup, the only ending that would've justified the tasteless storyline would've been for Booker to ultimately get the win.
At WrestleMania, an evil Triple H won the match after waiting 23 seconds following a Pedigree to cover Booker T for the pinfall victory. Many fans saw this as a huge disrespect to the WCW legend and feel it derailed his main event push.
3 Vince McMahon: Faced His Own Daughter In An I Quit A Match
Some months after Stephanie McMahon became SmackDown's babyface General Manager, she started a rivalry with Vince McMahon. At No Mercy 2003, Stephanie and Vince faced each other in an "I Quit" match.
The match ended when Vince choked out his daughter with a lead pipe and then Linda quit on behalf of her daughter to end Stephanie's reign as the General Manager.
2 Triple H: Turned On His Best Friend
After Shawn Michaels returned to wrestling in 2002, Triple H turned on his best friend. After betraying Shawn on-screen and explaining why he did it, Michaels was found knocked out in WWE's parking lot. His face was covered with his own blood.
Everyone assumed it was Triple H, but Hunter assured Shawn it wasn't him and would find the guy who did it. Of course, it was the truth was later unveiled when Michaels found the security footage that showed it was indeed The Game who attacked his best friend and put his head through a car window.
1 Vince McMahon: Sacrificed His Own Daughter
In 1999, The Undertaker formed The Ministry of Darkness and started taking orders from The Higher Power. After Backlash that year, Undertaker kidnapped Stephanie.
The next night on Raw, The Ministry tried to sacrifice Stephanie in a segment that crossed the line. She was tied to Undertaker's symbol and almost married The Phenom before Steve Austin saved the day. Later, Undertaker revealed that he had been following orders from Vince all along.