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Triple H is one of the most undeniable legends in WWE history—a fourteen-time world champion who has main evented WrestleMania seven times won two Royal Rumbles and otherwise been part of the fabric of the company for over twenty years. He’s widely regarded as one of the greatest heels in WWE history, besides which he also distinctively one of the most popular and recognizable acts the company has ever had—particularly for his remarkable longevity, spanning different eras of WWE programming. All of that’s without going into his behind the scenes role, not only marrying into the McMahon family but running the show for NXT and 205 Live while managing Talent Relations.
But what are Triple H’s very best moments? The Cerebral Assassin has a wide array of them when he has single-handedly elicited a huge response from fans and altered the WWE landscape in big ways. This article takes a look at five of The Game’s biggest and best moments of all time.
5. Returning From Injury, 2002
In 2001, Triple H got involved in one of the hottest angles of his career when he and Steve Austin teamed up as the Two Man Power Trip, a small heel supergroup that dominated the championship scene for the brief period they were active. Then Triple H tore his quad and brought the storyline to an abrupt end.
A lot happened in The Game’s absence, including the poorly received InVasion angle, Chris Jericho’s rise to the world title, and most of Stone Cold’s heel run. The fans were all too eager to welcome Triple H back, further fueled by some excellent video packages about his recovery and comeback leading up to his first appearance in months. The live audience gave him a hero’s welcome at Madison Square Garden, returning just before the 2002 Royal Rumble. He promptly planted Kurt Angle with a Pedigree to shore up his new face character, and demonstrate that he’d remain a top-level star.
4. Exiling Randy Orton From Evolution, 2004
The Cerebral Assassin aspect of Triple H’s character has seen him portray the mastermind behind a number of schemes. That included drugging and marrying Stephanie McMahon (in kayfabe), plotting Steve Austin getting run over in a parking lot, attacking Shawn Michaels upon his comeback to the ring, and facilitating Seth Rollins’s heel turn as he split from The Shield.
For all of these big moments, few are memorable or downright evil as his betrayal of young Randy Orton as Helmsley kicked him out of Evolution. The moment was particularly sharp because, while fans may have expected this to ultimately be how their partnership wound up, hardly anyone predicted as abruptly as it happened. Giving Orton the thumbs down was a brilliant, electric moment before Triple H had Batista drop The Legend Killer, en route to Helmsley leading a brutal beat down. While Orton’s face run may not have panned out as WWE hoped, this was nonetheless one of the most iconic moments of the era, and for Orton and Triple H’s respective careers.
3. Putting Over John Cena at WrestleMania 22, 2006
Triple H has enjoyed quite a few big wins in his career, getting the better of no lesser stars than Steve Austin, The Rock, Mick Foley, Randy Orton, and John Cena. Despite a reputation for politicking and winning matches he shouldn’t have necessarily taken, though, Triple H actually has a noteworthy record of putting over other stars in convincing fashion. That includes absorbing a beating from Ronda Rousey at WrestleMania 34, and tapping cleanly to Chris Benoit at WrestleMania 20 and Daniel Bryan at WrestleMania 30.
One of Triple H’s most noteworthy jobs came to Cena in the main event of WrestleMania 22. At a time when many fans were down on Cena and it looked as though WWE might cave to pressure and demote the young main eventer, Triple H tapped out to his STF in one of the biggest matches of the career. The outcome was shocking if for no other reason than defying expectations at the time, not to mention that it came at the end of a rock solid match. In this moment, The Game used his considerable clout in a concerted effort to get Cena over as the next top star in a terrific dramatic moment.
2. Rebooting DX After WrestleMania 14, 1998
WrestleMania 14 saw a changing of the guard as Stone Cold Steve Austin not only pinned Shawn Michaels to win his first WWE Championship but sent HBK packing into what would ultimately be a four-year retirement. With Michaels out, there was a greater weight on not only Austin, but other emerging top talents to carry the company.
Triple H had been Michaels’s second in command in DX, and it wouldn’t have been altogether unreasonable for the stable to have called it a day at that moment. Instead, Triple H doubled down on the group, announcing he was taking the reins in an impassioned promo, and introducing X-Pac as a new recruit.
This moment asserted that DX was there to stay and that as its new leader, Triple H was only moving up the card. While losing Michaels was certainly a blow to WWE programming, this was a defining moment for the Attitude Era as Triple H stepped up to fill his real-life friend’s void.
1. Gifting Kevin Owens The Universal Championship, 2016
Fall 2016, Triple H uncovered a new role for himself in what was already a wildly diverse career in WWE. He had been a part-time wrestler, and he had been a heel authority figure. When showed up on Raw, in the late stages of a match to crown a new Universal Champion after Finn Balor had to vacate it due to real life injury, we got Triple H as Deus ex-machine and figure of intrigue as he dropped in unannounced, dropped longtime ally Seth Rollins with a Pedigree, and handed Kevin Owens the Universal Championship.
This moment was a big surprise and arguably made even better because Helmsley mostly remained in the shadows for the months to follow, while Owens came into his own as a world champion and Rollins turned face. The table was set, though, for The Game’s eventual WrestleMania showdown with The Architect with one outstanding piece of business.
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