One would be hard pressed to find a man whose influence has touched as many parts of the professional wrestling business as Paul Levesque. When Levesque started working for the World Wrestling Federation in the mid-1990s it was under the name Hunter Hearst Helmsley. Helmsley was a prim and proper “Connecticut Blueblood,” and needless to say few could predict that a newcomer with such a whimsical character would someday be helping run the entire company.
That character eventually evolved into one of the leaders of D-Generation X, a foul and childish group of antiheroes who became one of the most popular wrestling stables in history when they led the charge into the Attitude era. After D-X had run its course by bringing the World Wrestling Federation to its knees, Helmsley, now referred to as Triple H, finally broke out into one of the most dominant and decorated solo runs of any wrestler to step in the ring.
Triple H’s reign as a top tier player has lasted for the better part of two decades, winning the WWE World Championship on fourteen occasions and remaining relevant to this day. He has faced his share of criticism for his spot in company after marrying Vince McMahon’s daughter Stephanie, but he has proven his worth with the rise of the ultra popular NXT on the WWE Network, which has produced nearly all of WWE’s current young Superstars. Triple H is a true living legend who has feuded and befriended the biggest names in the wrestling business. Here are 8 of his most famous allies and seven of his most notorious enemies.
15 Ally: Billy Gunn
As “Mr. Ass” he had his fair share of solo success, including runs with the WWE Intercontinental and Hardcore Championships as well as winning the 1999 iteration of the annual King of the Ring Tournament, but “Bad Ass” Billy Gunn is known most widely as a legendary tag team wrestler. His biggest claim to fame is that he was one half of the New Age Outlaws with Road Dogg Jesse James, a tandem that won the WWE World Tag Team Championship six times, although he is also remembered for a storyline with his tag team partner Chuck Palumbo where the two pretended to be in a romantic relationship for the purposes of fame and success.
As a unit, the New Age Outlaws were often part of the legendary D-Generation X and therefore allies with the team’s most consistent member, Triple H. This work relationship bled into real life and Gunn and Helmsley are close friends behind the scenes as well.
14 Enemy: CM Punk
If you were to ask a group of wrestling fans to compile individual lists of the most outspoken and controversial WWE Superstars of all time, CM Punk would likely top the list every single time. He’s certainly revered among the wrestling fan base with audiences all over the world chanting his name at WWE shows even years after the departure of the former WWE World Champion from the company, but he wasn’t immune to extreme misuse at the hands of his employer.
WWE notoriously “buried” CM Punk in his rivalry with Triple H and what resulted was Punk becoming one of Hunter’s most famous opponents. The disdain between the two isn’t limited to just the spectacle of wrestling, either; CM Punk has publicly commented on how the two have never seemed to be able to get along in interviews he has given since his widely covered falling out with WWE.
13 Ally: Road Dogg Jesse James
Originally playing the part of The Roadie and accompanying Jeff Jarrett to the ring, eventually the Road Dogg Jesse James set out on a much more lucrative career as one half of the New Age Outlaws beside “Bad Ass” Billy Gunn. Together, the Outlaws won many WWE World Tag Team Championships and the Road Dogg himself had a few memorable storylines as a singles wrestler, including a program with the freshly minted WWE Superstar Chris Jericho and a reign as the Intercontinental Champion.
The New Age Outlaws were also an important part of D-Generation X, and the Road Dogg seemed the perfect fit for the stable. James worked closely with Triple H for many years while part of that group and the two are legitimate friends, with James even holding a respected position still working with WWE in a behind the scenes role. The Road Dogg will always be closely associated with the Cerebral Assassin.
12 Enemy: John Cena
John Cena is the modern day version of a Hulk Hogan or a “Stone Cold” Steve Austin. He’s been competing at the main event level for nearly fifteen years as the top dog in World Wrestling Entertainment, feuding with just about everyone to ever have stepped foot in the company during this time. Cena has had legendary wars with The Rock, CM Punk, Randy Orton, Batista and of course, there’s no way Cena and Triple H weren’t going to cross paths. They did indeed, and they crossed paths very often.
Triple H and John Cena have battled so many times fans grew tired of seeing it happen, but that doesn’t mean these two didn’t deliver up to the expectations they’ve both come to command. When one of the greatest of all time meets the face of the company on the grand stage of WrestleMania, you can bet it’s one of the most talked about rivalries of either man’s career.
11 Ally: Ric Flair
As the crass and rebellious leader of D-Generation X, it didn’t seem obvious that Triple H would go on to be so closely aligned with one of the classiest acts in the history of pro wrestling. “The Nature Boy” Ric Flair is perhaps the most legendary grappler of all time with an officially recognized streak of sixteen World Championship reigns on his resume from just about every major wrestling promotion to ever have existed. He had already more than earned a Hall of Fame worthy career by the time he joined Triple H in WWE to help form Evolution.
Evolution is one of the most dominant wrestling factions of the last two decades and consisted of Triple H, Ric Flair, and a fresh-faced Batista and Randy Orton. It was this group that launched Batista and Orton into main event status as WWE Superstars and during this time Flair and Helmsley became good friends inside and outside of the ring.
10 Enemy: The Rock
Every man who becomes a legend in wrestling gets his start somewhere. One of the men who brought Triple H out of a group formation and into the spotlight as a solo wrestler was Dwayne “The Rock” Johnson. The Rock is one of the top five most famous pro wrestlers to ever compete, with lasting appeal which keeps bringing him back for special appearances after so many years beyond his retirement for an acting career in Hollywood. The Rock is a former WWE World Champion, Intercontinental Champion, and WWE World Tag Team Champion, and one of his greatest opponents was “The Game” Triple H.
Triple H’s battles with The Rock are the type of classic wars many fans remember so fondly from childhood and love to relive via the WWE Network. In particular, the two wrestled an instant classic Iron Man match at Judgment Day in 2000, one of the greatest matches of each man’s career.
9 Ally: Vince McMahon
Vince McMahon is sort of like a grandfather to wrestling fans all over the world. Though he wasn’t the original owner of the sensation that would become World Wrestling Entertainment, he inherited the business from his father and is the mastermind responsible for professional wrestling being known as it is today. In fact, it could be argued, and has been on many occasions, that if Vince McMahon didn’t turn the World Wrestling Federation into a global phenomenon in the 1980s we may not have a wrestling industry at all in 2016.
Many wrestling fans are well aware of all the times Vince McMahon stepped into the ring as a competitor himself. It all started with the sensational rivalry with “Stone Cold” Steve Austin which launched the business into new territory during the Attitude era, but McMahon has also competed with a slew of other Superstars including Triple H. However, Vince McMahon is actually quite close with “The Game,” as he is, of course, Triple H’s father in law and has given him quite a bit of power within the company.
8 Enemy: Daniel Bryan
To have been wrestling for WWE for so few years, Daniel Bryan achieved an unthinkable level of success. He became one of the most adored wrestlers in recent memory and racked up four reigns as the WWE World Champion, not to mention his other achievements such as winning the United States and Intercontinental Championships. He’s also fondly remembered for his time alongside Kane in Team Hell No as the WWE Tag Team Champions. What makes this all so much more special is the fact that most of it came as a result of organic fan reception, as WWE itself originally seemed to have no intentions of making Daniel Bryan a star.
It worked out pretty well for both parties, though. Being married into the McMahon family, Triple H naturally took a large portion of the heat from fans when Bryan wasn’t featured on the level they thought he deserved, so a feud between the two practically wrote itself. Because of all the attention Daniel Bryan’s surge to the top received, he’s easily one of Triple H’s top rivals.
7 Ally: Sean Waltman
Despite never becoming a World Champion, Sean Waltman had a long and illustrious career with WWE and even its competition during the Monday Night War, World Championship Wrestling. He got started in the World Wrestling Federation as the 1-2-3 Kid before moving on to WCW, where he was a part of the legendary New World Order faction. In WWE Waltman was a popular member of D-Generation X as X-Pac. X-Pac saw success in the tag team division as well as racking up reigns with the Intercontinental and European Championships during his singles runs.
Having worked so closely with Triple H during their D-X days, the two became close friends and remain such today. In fact, when Waltman was suffering from a serious substance abuse problem, Triple H personally went to his home to pick him up and get him into rehabilitation. There isn’t a much better example one can give of what makes a true friend.
6 Enemy: Mick Foley
Today Mick Foley’s known more for his most recent role as the General Manager of Raw, but once he was a savage, brutal brawler famous for some of the most sadistic spots in wrestling history. Foley had three alter egos known as Mankind, Dude Love, and Cactus Jack, all of which led him to a career which saw him inducted into the WWE Hall of Fame in 2013.
Over the years Mick Foley had countless run-ins with Triple H in a recurring rivalry that helped cement both men as two of the greatest performers in the history of the wrestling business. The incredible chemistry between the two saw them create magic in more than one classic encounter, one being at the Royal Rumble event in 2000 when Triple H defeated Cactus Jack in a deliciously vicious street fight. Mick Foley will undoubtedly go down as one of Triple H’s greatest enemies.
5 Ally: Kevin Nash
Kevin Nash is one of the more successful big men in wrestling. Nash first became known to fans as Diesel in the World Wrestling Federation, a bodyguard of sorts for a rising star known as “The Heartbreak Kid” Shawn Michaels. Diesel soon captured the WWE World Championship and became one of the longest reigning champions in the history of that title, before defecting to World Championship Wrestling at the onset of the Monday Night War and helping form the New World Order with Scott Hall and Hulk Hogan. In 2015, Nash was recognized for his contributions to pro wrestling with an induction into the WWE Hall of Fame.
Kevin Nash and Triple H were fast friends from their early days of working together in the WWF, forming what is known behind the scenes as “The Kliq” with several other wrestlers. They have remained close over the years and speak fondly of one another.
4 Enemy: “Stone Cold” Steve Austin
“Stone Cold” Steve Austin was inarguably the face of the Attitude era, the most lucrative time period in the history of WWE. Austin’s plethora of title reigns includes runs with the WWE World Tag Team, Intercontinental and WWE World Championships and he’s known worldwide for his feud with the boss, Vince McMahon, which set the wrestling world on fire in the late 1990s. Austin’s been a part of some of the most legendary WrestleMania wars to ever take place including battles with the “Heartbreak Kid” Shawn Michaels, Bret “Hitman” Hart, and most famously, Dwayne “The Rock” Johnson.
Steve Austin was already an established star when Triple H reached main event status and started winning championships. The two were heated rivals for years and were particularly at odds with Triple H was revealed as the man who had Steve Austin “ran over” on live television and nearly ended his career prematurely, leading to some of the most vicious matches of the Attitude era.
3 Ally: Shawn Michaels
Many fans and those inside the wrestling business itself consider the “Heartbreak Kid” Shawn Michaels to be the greatest big match performer in the history of the industry. It’s hard to argue that fact knowing that Michaels is one of the few men who can make any wrestler look amazing opposite him, not to mention the insane list of accomplishments HBK has at his disposal as bragging rights. He’s been a part of nearly all of WrestleMania’s greatest matches and held the Intercontinental and WWE World Championships on many occasions.
One of the defining eras in the long and storied career of Shawn Michaels came when he was at the helm of D-Generation X. He didn’t run that stable alone, however, as Triple H was right there with him for the entire ride. Along with the late WWE legend Chyna, Triple H and Shawn Michaels were the original members of D-X and became the best of friends over the years, something that still holds true today.
2 Enemy: Undertaker
You can talk about Ric Flair, Steve Austin, Hulk Hogan, Shawn Michaels or any other bona fide icon in the wrestling industry until you’re blue in the face, but only one of them can lay claim to being the most respected man in the business. That honor belongs to the Phenom, the Undertaker.
The “dead man” has been making history for nearly thirty years in WWE. He’s been WWE World Champion multiple times and been involved in some of wrestling's biggest feuds of all time, but that all pales in comparison to what the Undertaker managed to do with his lengthy undefeated streak at WrestleMania. That streak included three absolutely magnificent wars with Triple H in 2001, 2011 and 2012. It’s difficult to find more revered matches than these at any WrestleMania and they may just be the highlight of Triple H’s wrestling career, making the Undertaker perhaps his greatest rival.
1 Ally: Stephanie McMahon
Could there be any greater ally to Triple H than his own wife? Stephanie McMahon first became known to the WWE Universe in the late 1990s as a sweet and innocent girl next door type who was, inexplicably, the daughter of the vile WWE Chairman Vince McMahon. She quickly shed that image, though, and revealed herself to be just as dastardly as her father. Stephanie has abused her authority for years on WWE television and can even claim a Women’s Championship reign for herself.
Triple H and Stephanie McMahon were involved in a romance storyline during the Attitude era, one which eventually saw life imitate art when the two began dating in real life and tied the knot. They now have three children together and help Vince McMahon run the monster that is World Wrestling Entertainment. The power couple is set to inherit the kingdom of WWE one day and obviously have amazing chemistry together. Stephanie McMahon is undoubtedly Triple H’s greatest and strongest ally.
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