WWE Superstar and front office figure Triple H has had a career like few others in the industry. He could end up retiring with the most World championships in history. He's reformed his characters in a way that only Chris Jericho can relate. He's married to the boss's daughter -- Stephanie McMahon.

Triple H cemented his legacy as "The Cerebral Assassin," an extremely dirty, savage and evil character that went to great lengths in terrorizing and beating his opponents. It made him one of the top heels during the Attitude and Ruthless Aggression eras, and wrestling fans and historians continue to discuss The Cerebral Assassin character to this day.

But with that gimmick came plenty of vile actions by Triple H himself. Whether it was going great lengths to humiliate or attack fellow wrestlers, The Game always showed just how much he didn't care. His mission? To reign terror in the WWE. Here are the 15 most vile moment's of Triple H's career.

15 15. Breaking Big Show's Hand

Of course, Triple H's best way of beating the Big Show (a 7-foot monster weighing in at 500 pounds back in the day), would be to perform as one of the dirtiest people in the game. Back in 2005, The Game and Big Show did a contract signing for a title match at the 2006 edition of New Year's Revolution.

In the segment, Big Show began to attack Triple H, who managed to get the upper hand and got the World's Largest Athlete out of the ring. With Big Show's hand set firmly on the steel steps, The Game used a sledgehammer to hit it and break the hand. Triple H's plan? To break the right hand that Big Show used to chokeslam people.

Triple H broke it (in storyline), and would beat Big Show at New Year's Revolution.

14 14. Backstabbing Ric Flair at WWE Homecoming

After losing to Batista in at Vengeance in a Hell In a Cell match, Triple H took a few months off to rehab ongoing neck problems. That was essentially the end of Evolution, as Batista would move on to SmackDown, Ric Flair was left alone and The Game obviously taking time off.

But Triple H would return at WWE Homecoming in a Tag Team match with The Nature Boy. The two defeated Chris Masters and Carlito, but then The Game backstabbed his most trusted ally, attacking Flair with a sledgehammer.

Triple H instantly turned heel again, igniting a rivalry between him and Flair. This was an extremely savage moment for The Game, considering Flair stood by his side for months after Randy Orton and Batista left Evolution. It was definitely a Cerebral Assassin move, to say the least.

13 13. Handcuffing and Attacking Daniel Bryan

One of Daniel Bryan's best feuds came with Triple H and The Authority during the 2014 calendar year. The rivalry between these two (in storyline, of course), reached a point where Stephanie McMahon brought out multiple police officers to arrest Bryan for attacking Triple H the night before a Raw episode.

Bryan was arrested and handcuffed by police, only for The Game to tell them that they were to let him go, and that they "weren't real cops." Triple H then dismissed them before brutally attacking Bryan for minutes. The Game tormented Bryan for minutes, attacking him on the table, throwing him into the wall and giving him the Pedigree in the middle of the ring. To make things even worse, The Game mocked Byran's "YES" chant.

12 12. Placing A "Bounty" on Goldberg

In 2003, Triple H was in the middle of a heated rivalry with Goldberg -- the face of WCW for a couple of years before its demise. Frustrated by Goldberg's unwillingness to give up, The Game placed a $100,000 bounty on anyone who could finally stop the former professional football star.

That recruited The 6-foot-6, 300-pound muscle machine, Batista. The Animal came out and attacked Goldberg during a match against Shawn Michaels, placing his foot in a chair before stomping on it.

Triple H got someone to do his dirty work, and Evolution would be formed shortly thereafter. Getting a big man to take out another guy for money, because you can't do it yourself? Indeed, The Cerebral Assassin really has had a knack for finding creative ways to pull of vile acts.

11 11. Getting Rikishi to Run Over Steve Austin

The main event of the 1999 edition of Survivor Series was a Triple-Threat WWE Championship match, originally scheduled to have The Rock, Triple H and 'Stone Cold' Steve Austin face off. But Austin was "run over by a car", and was thus replaced by Big Show in the match.

Big Show would end up as the champion, and Austin was essentially screwed out of winning the title. It was later revealed that Triple H himself set up a plot to have Rikishi run over Steve Austin with a car.

Austin was out of action for nine months, though in reality he had to take significant time off to recover from a series of injuries he had suffered. But in storyline? It was just yet another vile act by Triple H himself.

10 10. Attacking Batista With A Sledgehammer

Triple H was fuming angry that Batista had backstabbed him before the latter went on to win the World Heavyweight Championship at WrestleMania. With only Ric Flair left by his side, The Game came up with a plan.

Batista and Flair had shown respectable for one another, embracing in the middle of the ring despite their recently-formed rival. But when Triple H game out, Flair delivered a low blow to the animal, who then became defenceless. Together, Triple H and Flair attacked Batista, highlighted by a sledgehammer shot to the face. Triple H then took a bloodied Batista and Pedigreed him onto the world title belt.

Hey, if you don't think you can beat a guy one-on-one, just get the Dirtiest Player in the Game to help. Then attack him with a sledgehammer. Triple H? Attacking with a Sledgehammer? YOU JUST MADE THE LIST!

9 9. Smashing Roman Reigns Into The Table

Triple H and Roman Reigns got into quite the feud near the end of 2015 and in the beginning of 2016. After attacking Triple H and sending him off in a stretcher, The Game returned a few weeks later to win the Royal Rumble (and the WWE World Heavyweight Championship to go with it).

During a Feb. 2016 segment, Triple H came out to brutally attack Reigns a few weeks before their match at WrestleMania. The game proceeded to take Reigns' face and slammed it into the announcer's table for nearly 20 full seconds, then punching him as he started to bleed miserably.

Triple H finished off the attack by giving Reigns a pedigree on the steel steps, leaving the blooded and defenceless Reigns embarrassed. Just another savage moment by none other than The Game himself.

8 8. Assaulting Eugene With Evolution

Remember that miserable storyline where Eugene was Eric Bischoff's nephew? Well, Eugene began to rise as a star by becoming friends with Triple H, who became buddy-buddy with him. Eugene had a World title match on an episode of Raw against Chris Benoit, trying to impress The Game.

Eugene thought he pinned Benoit to win it, not knowing that the latter placed his foot on the ropes at the last second. Evolution came out to supposedly congratulate Eugene on his victory.

Evolution attacked Benoit, William Regal and then brutally attacked Eugene which left him in a bleeding mess. This attack featured multiple Pedigrees by Triple H on Eugene himself, once again showing his ultra-evil inner-self. Eugene would later get his revenge by assisting Benoit in taking down The Game in a World Heavyweight Championship match.

7 7. Kicking Randy Orton Out Of Evolution

The point of Evolution was for Ric Flair (the past), and Triple H (the present), to guide Randy Orton and Batista into becoming "the future." They did just that, as Orton upset Chris Benoit at the 2004 edition of SummerSlam to become the youngest World Heavyweight Champion ever (at the age of 24).

Benoit invoked his rematch clause on the following episode of Raw, but lost to Orton who got some assistance from his allies. Evolution began to celebrate with Orton, who was hosted onto Batista's shoulders.

The Game put his thumbs up, then turned them down and ordered Batista to drop him. The trio then attacked Orton, brutally assaulting him until he was left bleeding. This ignited a memorable feud between the two parties, one that lasted about a half-year. But kicking out your own member just cause he was the world champion? Vile, Mr. Triple H.

6 6. Racist Segment With Booker T

Triple H would face Booker T for the World Heavyweight Championship match at WrestleMania XIX. Unfortunately, what could have been a great storyline and feud was marred by one of the most controversial angles in WWE history.

In the storyline, Triple H tried to play it off that people of Booker T's African American race weren't suit to be champions. Here's what he said in a segment, according to the Rolling Stone:

"Somebody like you…doesn't get to be a world champion. People like you don't deserve it."

In the angle, The Game tried to play it off as not being racist, but simply just bringing up Booker T's past lifestyle as a criminal. Nonetheless, this angle didn't sit well with fans, and it's one of the most vile storylines Triple H ever participated in.

5 5. Smashing HBK Through A Window

After retiring to rehab injuries and his alcohol/drug addictions, Shawn Michaels returned to the WWE in 2002 as a member of the reformed New World Order alliance consisting of Hulk Hogan, Kevin Nash and Scott Hall.

Triple H reformed his old friendship with Michaels, only to see that The Heartbreak Kid had had his faced smashed through a car window. Triple H vowed to find out the perpetrator, but it was later revealed that The Game himself was behind the crime.

Michaels and Triple H cut a promo on Raw, where HBK revealed surveillance footage that showed The Cerebral Assassin did it. The Game showed no regret nor remorse, saying how Michaels' ego was too much. This would set off a new rivalry between the two -- Triple H smashing his friend's face through a window.

4 4. Attacking William Regal (On a Stretcher)

Trying to get revenge for his friend Eugene, William Regal faced Triple H in a match on Raw (shortly after the aforementioned Attack Evolution carried out on Eugene). Triple H began to attack Regal with a sledgehammer, as the defenceless Brit lay in the ring gushing out blood.

Officials and paramedics put Regal on a stretcher to perform medical attention. Triple H began to walk away, only to turn his back and flip the stretcher over. All of this simply because Regal was looking to avenge The Game for attacking his buddy.

A sledgehammer attack? Leaving a guy bleeding? Forcing him to go onto a stretcher? Throwing him off the stretcher and gloating about it? Triple H has been one very vile man all these years.

3 3. Giving His Wife The Pedigree

Triple H and Stephanie have been happily married for a decade-and-a-half now. They have three daughters together, are WWE's ultimate power couple and have helped Vince McMahon sustain the success of the company. So why on earth would the game be so brutal towards his own wife?

There have been a couple of occasions where Triple H performed the Pedigree on his own wife. In one of the segments, he took his frustration out on Stephanie by putting her on the announce table and giving her the Pedigree.

Of course, this is all storyline, and he's way too nice of a guy to commit such an act in real life. But since this article is based on the worst things Triple H has done as a character, giving the pedigree to his wife makes the list.

2 2. Kidnapping, Drugging and Marrying Stephanie

In 1999, Triple H began a feud with Vince McMahon. He took it to a personal level by targeting the boss' daughter. In storyline, Triple H presented a video to the boss where he had married Stephanie McMahon in Vegas. Triple H had kidnapped and drugged Stephanie, marrying her against her own will.

Without having to go into much explanation, this was easily one of the most savage and vile moments any wrestler has done in storyline. To kidnap, drug and force a woman to marry you? That's one thing, but it's even worse when you do it to the boss's daughter.

This storyline took a major twist when Stephanie revealed that she was actually aware of the plot and agreed to marry Triple H. This was to get revenge on her father, as Stephanie then switched allegiance and formed a relationship with The Game.

1 1. Involvement In The Katie Vick Storyline

This is among the grossest storylines in WWE history, one I'd much rather never write about. But I'll reluctantly do so, in case you aren't aware of what happened.

During the Attitude Era, Triple H had a rivalry with Kane. To embarrass the Big Red Machine, The Game revealed a humiliating secret -- that Kane was driving with girlfriend Katie Vick, who proceeded to inadvertently kill her in a car accident. Triple H decided to take things a step further, though.

In this storyline, The Game donned Kane's mask and posed as the 7-foot-tall giant. Triple H went into a casket and started to sexually assault a mannequin (which was supposed to be Katie Vick's body).

This is widely recognized as arguably the worst storyline in WWE history. One that was just gross, unnecessary and missed up in so many ways. Easily the most vile moment for the career of Triple H.