Triple H and Stephanie McMahon's 10 Greatest Heel Moments

Erik BeastonFeatured ColumnistMarch 24, 2014

Triple H and Stephanie McMahon's 10 Greatest Heel Moments

0 of 10

    Credit: WWE.com

    For nearly 14 years, Triple H and Stephanie McMahon have served as WWE's resident power couple, both onscreen and off.

    They have made life a living hell for many a WWE Superstar and have shown a propensity for doing whatever is necessary to ensure a favorable outcome for themselves. The Rock, Kurt Angle, Steve Austin, Shawn Michaels, Daniel Bryan, Big Show and the Rhodes family are just some of the notable names to suffer the wrath of the billion-dollar couple, and with Triple H potentially capturing yet another WWE Championship at WrestleMania XXX, it may get far worse before it gets better.

    Last Monday night on Raw, the couple was united and stronger than ever as they set Bryan up for a brutal and violent beating. With two more weeks to go until the biggest show of the year and a match with the Aberdeen native, what could Triple H and Stephanie have in store for the leader of the Yes Movement?

    In celebration of the couple's return to their wicked, diabolical ways, here is a look back at some of their greatest and most notorious heel moments, ranked in chronological order.

Hit and Run

1 of 10

    It does not get much more villainous than orchestrating a vehicular assault of another human being.

    While it would not be revealed until nearly a year later, Triple H did just that at the 1999 Survivor Series when he recruited Rikishi to run down "Stone Cold" Steve Austin in the parking lot of the Joe Louis Arena in Detroit.

    Austin, along with The Rock, was scheduled to compete in a Triple Threat match against The Game for the WWE Championship in the main event of the annual November event. During a backstage promo, he was approached by Triple H and a brawl ensued. Austin chased his rival outside and fell prey to a charging car, which accelerated and ran him over.

    The incident sidelined Austin for 10 months and allowed Triple H to finally break through the glass ceiling and become one of the top stars in the industry.

    When it was revealed that Triple H was behind the assault, his feud with Austin was revisited and intensified. They met at Survivor Series 2000 and, three months later, did battle in a 3 Stages of Hell match that saw The Game defeat Austin in a bloody Match of the Year candidate.

The Dawn of the McMahon-Helmsley Era

2 of 10

    The main event of December 1999's Armageddon pay-per-view featured Vince McMahon's attempt to avenge his daughter's honor and his own pride as he took on Triple H in a Street Fight.

    The feud between the two had become increasingly personal over the fall months, beginning when McMahon ended Triple H's first WWE Championship reign in September and reaching its climax when it was revealed that The Game had married an unconscious Stephanie McMahon while in Las Vegas, ruining a grand wedding ceremony on a live episode of Monday Night Raw.

    The hatred between the two would boil over in a bloody and violent street fight in Fort Lauderdale, Fla. The action spilled from the ring all the way to the parking area outside the arena before returning. McMahon fought back admirably and, late in the match, appeared to have the upper hand following some well-timed strikes.

    Then Stephanie, who was seated at ringside for the match, hopped over the guardrail and urged her father to let her hit Triple H with a sledgehammer. As much as it appeared as though she wanted to, however, she could not bring herself to do it. Triple H grabbed the weapon, blasted McMahon with it and, moments later, scored the pinfall victory.

    After the match, Stephanie suddenly dropped the concerned daughter act, rose to her feet and embraced Triple H, revealing an alliance that would dominate WWE over the next year.

Pink Slip on a Pole

3 of 10

    Triple H and Stephanie McMahon-Helmsley found great enjoyment in toying with the livelihood of their rivals early during their reign of terror over WWE.

    On the December 27, 1999 episode of Raw, they booked a Pink Slip on a Pole match between The Rock and Mankind in which the loser would be fired from WWE. Rock and Mankind had formed the successful Rock and Sock Connection and, as two of the more decorated and popular stars on the roster, were direct threats to the McMahon-Helmsley regime.

    Rock and Mankind fought admirably for their livelihoods, and in the end, it was the Great One who managed to secure the pink slip from the pole and ensure Mankind's termination from the company.

    Just two days removed from Christmas, and with a family to support back in Long Island, Mick Foley found himself unemployed.

    The Rock, in a rare show of support for the one Superstar he could consider a friend, organized a protest by the men and women in the locker room shortly thereafter. The entire roster threatened to walk out of WWE if Foley was not reinstated.

    He was.

    The match was a bit of booking brilliance. The concept of the manipulative bosses playing with the lives of their employees, seemingly for their own enjoyment, really helped to get Triple H and Stephanie over as the most hated characters in WWE and set the stage for an outstanding rivalry between Foley and The Game, which would culminate in a five-star classic Street Fight at Royal Rumble.

The Slap Heard 'Round WWE

4 of 10

    By the time WWE embarked on the road to WrestleMania 2000, the McMahon-Helmsley Era was in full force, and Triple H and Stephanie McMahon had become the hottest heel act the business had seen since the heyday of the Mr. McMahon character two years earlier.

    With the WrestleMania main event featuring four Superstars and a McMahon family member in every corner, it was only a matter of time before the dysfunctional family drama began to dominate WWE programming.

    Fans had seen Vince and Shane feud on television before, and Stephanie had been phenomenal in her role as the spoiled, bratty daughter of the chairman. Vince's wife, Linda, however, had remained the one innocent and sympathetic figure in the entire deal. She had virtues and tried to do the right thing regardless of the consequences.

    The idea of anyone doing anything to hurt her, especially of a physical nature, was unfathomable. Yet that is exactly what happened when she was confronted by Stephanie on an episode of SmackDown.

    To the shock and awe of the WWE fans, Stephanie struck her mother down with a slap.

    The Attitude Era featured plenty of raunchy, violent and controversial behavior, but Stephanie slapping her mother was among the most shocking moments in WWE history. It was a sign of disrespect and showed just how much the relationship with Triple H had transformed "daddy's little girl" from the sweet young woman fans had gotten to know in 1999 to the vindictive vixen of 2000. 

Stephanie, Vince and William Dump Trish

5 of 10

    Stephanie McMahon's feud with Trish Stratus in early 2001 was not only incredibly entertaining, it also ranks as one of the best female feuds that WWE has ever produced.

    Trish had taken to seducing Mr. McMahon, his billions of dollars undoubtedly on her mind. The two engaged in public displays of affection on a regular basis, and their affair even led to Linda McMahon going into a catatonic state.

    Naturally, the idea that a younger woman was moving in on her father enraged Stephanie, and a rivalry between her and Trish erupted. Stephanie got the first laugh when she booked Trish in a Spanking match against Jacqueline. A month later at the Royal Rumble, the Divas engaged in a catfight that took the attention away from the WWE title match between Triple H and Kurt Angle and saw Vince planted squarely in the middle.

    Prior to the No Way Out pay-per-view in February of 2001, Trish attacked Stephanie at a makeshift farm show held in the bowels of the arena and humiliated her by pouring what appeared to be liquid manure all over the Billion Dollar Princess. Days later, Stephanie capitalized on interference from William Regal to defeat Trish in a very good match at No Way Out.

    All of that set the stage for a mixed tag match on the February 26 episode of Raw in which Vince teamed with Trish to take on Stephanie and Regal. Prior to the match, the chairman of the board had stirred up some nauseating concoction in a yellow janitor's bucket and promised to use it during the match.

    He did.

    On Trish.

    To the surprise of some, McMahon unceremoniously dumped Trish in the most humiliating of fashions, berating her and then covering her in the brown slop from the bucket. Stephanie revealed that she was on the same page as her father, and both daddy and daddy's little girl embraced in the center of the ring.

'I See You for What You Truly Are'

6 of 10

    Triple H's return from a torn quadriceps in 2002 instantly made him one of the most popular stars in the business and created an interesting dynamic between him and Stephanie McMahon, his onscreen wife. She was still the most hated female in all of WWE, but fans clearly wanted to support her husband.

    The easiest way to solve the problem was to split them up, and that is exactly what happened when it was announced that the loving couple would renew their vows on the February 11 episode of Raw.

    To convince the Game to go along with the ceremony, Stephanie revealed that she was pregnant. She even had a doctor come to Raw to discuss ultrasound results and the health of the child.

    Just prior to the ceremony, however, Linda McMahon phoned her son-in-law and revealed that Stephanie had been lying and that the doctor that had visited Raw was simply an actor. She sent video proof, and the happiness that had painted Triple H's face suddenly disappeared, replaced with anger and rage.

    Playing it cool, he went to the ring, stood patiently by during the pomp and circumstance of the ceremony, then dropped the bomb on his wife and her father, Vince. He revealed that he knew everything, used profanity to describe his wife and then planted Vince with a Pedigree.

    The Game shoved Stephanie to the mat and tossed his wedding ring at her as he left the arena to a huge ovation.

    Proving that she had learned a lot from her husband, Stephanie knew what she wanted and stopped at nothing to get it, manipulating her spouse's feelings with the promise of a child. Ultimately, Stephanie got what was coming to her, but for those few months leading up to the ceremony, it was difficult to imagine another performer in WWE as hated as the boss' daughter.

Kane...You're a Murderer

7 of 10

    If vehicular assault is not enough to confirm Triple H as one of the most dastardly villains in WWE history, accusing a fellow Superstar of murder and necrophilia certainly should.

    In September of 2002, Kane returned from injury and instantly became one of the hottest heels in wrestling. He was very popular and was showing sides of his personality that fans had not previously been exposed to. He was a natural choice to challenge Triple H for the World Heavyweight Championship at October's No Mercy pay-per-view.

    Realizing he could not match Kane's physical nature nor the momentum that he had gained since his return, The Game opted to focus on mind games in an attempt to throw the Big Red Monster off mentally.

    After a hard-fought victory in a TLC match for the World Tag Team Championships, Kane stood helplessly in the center of the ring and listened as Triple H accused him of murdering his own girlfriend, Katie Vick. In the weeks that followed, the accusations only increased in absurdity. Triple H accused Kane of engaging in necrophilia with Vick's corpse and even had himself filmed mocking the ordeal.

    It was a completely ludicrous storyline that ranks as one of the worst in professional wrestling history.

    The mind games worked, as Triple H defeated Kane to retain the World Heavyweight title. While the angle was absolutely offensive, it did show the lengths to which The Game would go to retain the title that he held so near and dear.

A Lesson in Humility

8 of 10

    Randy Orton's meteoric rise in 2004 should have been a happy occasion for Triple H. After all, he had claimed that he would help make the third-generation star into one of the top performers in the sport and he did just that. At SummerSlam in August of 2004, Orton defeated Chris Benoit to capture the World Heavyweight Championship, becoming the youngest competitor to ever do so.

    The following night on Raw, he defeated Benoit in a rematch.

    As he celebrated with his Evolution teammates, Orton was lifted high into the air on the shoulders of Dave Batista. It was a magical moment as Triple H stood down on the ground giving him a big thumbs up, seemingly congratulating him for a job well done. 

    Then it happened. The thumbs up turned to a thumbs down, and Triple H ordered Batista to drop Orton, something The Animal seemed all too happy to do. From there, Ric Flair joined his teammates in a beatdown of the young new champion, leaving him a bloody mess to close out the show.

    It was yet another reminder that the World Heavyweight Championship meant the world to The Game and that he had no problem at all with taking out or betraying anyone who stood between him and his title.

The Rise of The Authority

9 of 10

    The SummerSlam 2013 main event between Daniel Bryan and John Cena should have been the crowning achievement in Bryan's critically acclaimed career. He had worked his way up from gymnasiums to Ring of Honor to WWE and was competing in the top match of the second-most important pay-per-view of the year against the man who had carried WWE on his back for nearly a decade.

    The moment he caught Cena with the running knee and pinned him for a three-count, courtesy of guest referee Triple H, the fans inside the Staples Center in Los Angeles became unglued. They greeted the title reign with a huge pop, the handshake from Cena to the new champion with another wave of cheers and the pyro and confetti that fell in celebration of the new titleholder with one more burst of positive reactions.

    Then it happened.

    Rev Theory's "Voices" played over the PA system, and Randy Orton made his way to the ringside area, his Money in the Bank briefcase in hand. He teased cashing it in but seemingly thought better of it. Suddenly, Triple H spun Bryan around, planted him with the Pedigree and Orton sprinted to the ring. He covered Bryan, and the COO of the company counted the pinfall before rewarding the new champion with his prize.

    It was a shocking twist to end the best pay-per-view of the year and the start of an angle that would stretch eight months and see Triple H and wife Stephanie cut Bryan off at every turn.

Deceit Leads to Brutality

10 of 10

    The March 17 episode of Raw featured a classic heel beatdown from Triple H, aided by wife Stephanie, that was reminiscent of those fans bore witness to during the Attitude Era.

    After feigning respect for Bryan, Triple H watched as Stephanie ordered security to detain Bryan and arrest him on charges of public endangerment. The COO protested, or so we thought, before entering the squared circle and calling off the officers.

    He then revealed his true intentions as he beat Bryan senseless while the Aberdeen native was helpless, handcuffed and unable to protect himself.

    The beating spilled from the ring to the arena floor, where Triple H repeatedly dunked his head in water, slammed him on the announce table and delivered a vicious steel chair shot to the top of the head. Stephanie joined in the fun, slapping the face of Bryan and verbally assaulting him at the same time.

    Back inside the squared circle, Triple H finished the violent beating off with a Pedigree.

    The sight of WWE's power couple engaging in a kiss while standing over the body of the most popular star in the sport served as a reminder that, until they are informed otherwise, they are in control of the WWE Universe and no one can stop them.