Beloved in the Attitude Era for his role in the stable D-Generation X, Triple H became an even bigger star in the Ruthless Aggression Era. During this run, he became not only a multi-time world champion, but a top heel at the same time, dominating WWE’s main event scene on Raw in what fans have since described as his “Reign of Terror.”
The Ruthless Aggression Era ran from roughly June 2002 to July 2008, which means that Trips engaged in a ton of feuds against some of the biggest names in WWE at the time. Let’s take a look at the biggest rivalries of this period, starting with the worst.
10 Booker T
For many wrestling fans, Triple H’s rivalry with Booker T was the nadir of Trips’ Reign of Terror. A five-time WCW World Champion, Booker T got the opportunity to challenge Triple H for the World Heavyweight Title at 2003’s WrestleMania 19. In the build to the bout, their feud took on a racial quality as the champion cut promos stating that people like Booker T don’t get to have Trips’ success. This may have proven to be an incredible angle if Booker T won the match, but it was Triple H who stood victorious.
9 Kane
In the fall of 2002, Triple H got into a feud with Kane that resulted in what might be the most infamous storyline of both wrestler’s careers. As their rivalry intensified, Triple H revealed Kane’s traumatic past with a woman named Katie Vick, which ventured far outside the realm of good taste with its incorporation of necrophilia. That sounds like it would have led to a big stipulation like Hell in a Cell, but it was all in service of a regular singles match to unify the World Heavyweight Championship with the Intercontinental strap.
8 Scott Steiner
When Scott Steiner returned to WWE in 2002, he was already a multi-time tag team champion who, by the end of WCW, had found his footing as a singles star. Unfortunately, his WWE run in the 2000s left a lot to be desired, especially as he entered a feud with Triple H. Steiner’s challenge for Triple H’s World Heavyweight title at Royal Rumble 2003 has the dubious distinction of being one of the worst matches in the pay-per-view’s history — and their rematch at No Way Out didn’t fare much better.
7 Goldberg
Another WCW main eventer who had a lackluster WWE run in the early 2000s was Goldberg, who overall failed to recapture the mystique he had during his time with the competition. However, he still entered the main event scene, where he feuded with Triple H for the World Heavyweight Title.
At Unforgiven 2003, Goldberg put his career on the line to beat Triple H for the Big Gold Belt, kicking off a 84-day reign with weak rematches at Survivor Series and on Raw. Eventually Triple H won the belt back from Goldberg in a Triple Threat Match, pinning the champ after a Chokeslam from Kane.
6 Kevin Nash
Given that they were close buddies in their backstage social group called The Kliq in the mid-1990s, fans might be surprised to find out that Kevin Nash and Triple H had a surprisingly lackluster feud in 2003. The feud kicked off strong with Triple H making Nash choose to remain friends with himself or Shawn Michaels, only to attack him when the former Diesel struggled with the decision. Unfortunately — save for their climactic Hell in A Cell Match at Bad Blood 2003 — most of the feud failed to satisfy.
5 John Cena
In 2006, Triple H won a three-week tournament on Raw, earning a title match against WWE Champion John Cena at WrestleMania 22. Trips and Cena were never one another’s biggest rivals, but their feud proved to be solid stuff, with Cena getting a strong submission victory over the veteran. More matches ensued between the two, with Cena retaining against Triple H and Edge weeks later at Backlash, followed by both men failing to capture the WWE Title from Randy Orton at WrestleMania 24 in 2008.
4 Batista
One of John Cena’s contemporaries, however, proved to be a top rival for Triple H. The two men were already stablemates in Evolution, but a 2005 Royal Rumble win ended up putting Triple H’s World Heavyweight Championship in Batista’s sights. Despite Trips’ efforts to get him to challenge for SmackDown’s WWE Championship, Batista chose to go after the World Heavyweight Belt instead.
Batista proved to be the one who essentially ended Triple H’s Reign of Terror not only by dethroning the champ at WrestleMania 21, but by also being the first wrestler to pin Triple H in a Hell in a Cell match a couple months later at Vengeance.
3 Randy Orton
Before feuding with Batista, however, Triple H turned on Randy Orton first, betraying his Evolution protege due to Orton’s capturing of the World Heavyweight Title from Chris Benoit. A big rivalry between the two ensued, resulting in Triple H regaining the belt and retaining it in following encounters with Orton. Even before their feud really ramped up in 2009 — although their big showdown at WrestleMania 25 didn’t live up to the build — Orton and Triple H put on some seriously intense, exciting bangers at multiple pay-per-views.
2 Ric Flair
Triple H really did feud with every single one of his Evolution compatriots, including Ric Flair. While Triple H experienced a four-month layoff from in-ring competition, Flair experienced a bit of a face turn, perfectly setting the stage for Trips to turn on his mentor upon returning in fall 2006. Two standout matches ensued from this angle — a Steel Cage Match at Taboo Tuesday followed by a Last Man Standing match at Survivor Series. Even outside of the Evolution relationship, this classic feud had added weight because Triple H was personally a huge fan of Ric Flair.
1 Shawn Michaels
The year 2002 marked the triumphant return of Shawn Michaels to professional wrestling after taking four years off due to what was thought to be a career-ending injury. While it seemed like Triple H and Michaels were getting the band back together and reforming D-Generation X, Triple H turned on him, kicking off a blood feud between the former friends. This led to a number of great, intense matches including an Unsanctioned Street Fight at SummerSlam and a Three Stages of Hell Match at Armageddon.