Triple H

In early 1990, Levesque began to train as a professional wrestler at Killer Kowalski's school in Malden.[4][16] His classmates included fellow future WWF wrestlers Chyna and Perry Saturn. He made his professional debut on March 24, 1992, in Kowalski's promotion, the International Wrestling Federation (IWF), under the name "Terra Ryzing", defeating Tony Roy.[19] In July 1992, he defeated Mad Dog Richard to win the IWF Heavyweight Championship.[1] Managed by John Rodeo, he wrestled for various promotions on the East Coast independent circuit until 1993.[20]

In early 1994, Levesque signed a one-year contract with World Championship Wrestling (WCW).[15][21] In his first televised match, Levesque debuted as a villain named Terror Risin', defeating Keith Cole. His ring name was soon modified to Terra Ryzing, which he used until mid-1994, when he was renamed Jean-Paul Lévesque.[5][22] This gimmick referred to his surname's French origins and he was asked to speak with a French accent, as he could not speak French.[23] During this time, he began using his finishing maneuver, the Pedigree.

Levesque had a brief feud with Alex Wright that ended on December 27 at Starrcade[5] with Wright pinning him.[24] Between late 1994 and early 1995, Lévesque briefly teamed with Lord Steven Regal, whose upper class British persona was similar to Lévesque's character.[22] The team was short-lived, however, as Levesque left for the World Wrestling Federation (WWF) in January 1995 after WCW turned down his request to be promoted as a singles competitor.

Helmsley wore a tailcoat suit and carried a traditional atomizer perfume bottle to highlight his extreme snobbishness.

In a modified version of his gimmick in WCW, Levesque started his WWF career as a "Connecticut Blueblood".[23] According to Levesque, J. J. Dillon originally gave him the name of Reginald DuPont Helmsley, but Levesque asked for a name to play with the first letters and management ultimately agreed to his suggestion of Hunter Hearst Helmsley.[25] He appeared in taped vignettes, in which he talked about how to use proper etiquette, up until his wrestling debut on the April 30, 1995 episode of Wrestling Challenge defeating Buck Zumhofe.[26] Helmsley made his WWF pay-per-view debut on August 27 at SummerSlam, defeating Bob Holly.[27] Helmsley remained undefeated during the early months of his career, suffering his first pinfall at the hands of The Undertaker in a Survivor Series match at the namesake event. In the fall of 1995, Helmsley began a feud with the hog farmer Henry O. Godwinn, culminating in an infamous Hog Pen match on December 17 at In Your House 5: Seasons Beatings, where Helmsley was victorious.[28]

Helmsley in 1996

After being highly promoted in the first few months after his debut, his career stalled during 1996, starting off with a feud with Duke "The Dumpster" Droese following a loss during the Free for All at 1996 Royal Rumble.[29][30] Up until that event, his angle included appearing on television each week with a different female valet (which included Playboy Playmates Shae Marks and Tylyn John).[5] It was during this time that Helmsley suffered his first loss in singles competition in WWF, against Bret Hart on the March 4 episode of Raw. Sable would become Helmsley's valet at WrestleMania XII on March 31 and after his loss to The Ultimate Warrior,[31] as part of the storyline, he took his aggressions out on her. The debuting Marc Mero – her real-life husband – came to her rescue, starting a feud between the two wrestlers.[32]

On June 1, 1996, Hunter appeared on an episode of Superstars in a match against Marty Garner.[33] When he attempted to perform the Pedigree, Garner mistook the maneuver for a double underhook suplex and tried to jump up with the move, causing him to land squarely on top of his head and suffer neck damage.[33] Garner reportedly sued the WWF, eventually settling out of court. However in 2020, Garner affirmed there was no lawsuit.[34]

He was known backstage as one of the members of The Kliq, a stable of wrestlers including Shawn Michaels, Kevin Nash, Sean Waltman and Scott Hall, who were known for influencing Vince McMahon and the WWF creative team.[29] It has been claimed that he was scheduled to win the 1996 King of the Ring tournament, but the victory was instead awarded to Stone Cold Steve Austin after the Madison Square Garden Incident, in which the Kliq broke character after a match to say goodbye to the departing Nash and Hall.[35] Despite the punishment, Helmsley did have success following the MSG Incident. Mr. Perfect became his manager and he won the Intercontinental Championship for the first time on October 21, by defeating Marc Mero.[32][35] When Mr. Perfect left the WWF, his departure was explained to be a result of Helmsley turning his back on his manager as soon as he won the Intercontinental Championship. Helmsley held the title for nearly four months before dropping it to Rocky Maivia on the February 13, 1997 special episode of Raw, called Thursday Raw Thursday.[36] For a very brief time, Helmsley was accompanied by Mr. Hughes, who was his storyline bodyguard reminiscent of Ted DiBiase and Virgil.[37] After losing the title, he feuded with Goldust, defeating him on March 23 at WrestleMania 13.[38] During their feud, Chyna debuted as his new bodyguard.[39]

Helmsley was being highlighted again in 1997, winning the 1997 King of the Ring tournament by defeating Mankind in the finals.[35][40] Later that year, Shawn Michaels, Helmsley, Chyna and Rick Rude formed D-Generation X (DX). This stable became known for pushing the envelope, as Michaels and Helmsley made risqué promos—using the catchphrase "Suck It" and a "crotch chop" hand motion[41]—and sarcastically derided Bret Hart and Canada. By that point, Helmsley had all but dropped the "blueblood snob" gimmick, appearing in T-shirts and leather jackets. During this period, his ring name was shortened to simply Triple H, though he was still called Helmsley from time to time and Hunter for the rest of his career.[35] Even after the DX versus Hart Foundation storyline ended, he continued to feud with the sole remaining Hart family member Owen over the European Championship, which Helmsley won by "defeating" Michaels after Michaels laid down for him on December 11, which aired on the December 22 episode of Raw is War. Triple H lost the title to Hart after The Artist Formerly Known as Goldust competed against Hart in a drag as Triple H on the January 22 episode of Raw is War. Triple H defeated Hart to win his second European Championship on the March 16 episode of Raw is War. At WrestleMania XIV on March 29, Triple H defended the title against Hart in a rematch, with the stipulation that Chyna had to be handcuffed to then-Commissioner Sgt. Slaughter. Triple H won after Chyna threw powder into Slaughter's eyes, momentarily "blinding" him and allowing her to interfere in the match.

Triple H and then-girlfriend Chyna in April 1999

After WrestleMania, Shawn Michaels was forced into temporary retirement due to a legitimate back injury sustained in January at the Royal Rumble,[42] with Triple H taking over the leadership position in DX,[35] claiming that his now-former associate had "dropped the ball". He introduced the returning X-Pac the night after WrestleMania and joined forces with The New Age Outlaws.[35][43] As 1998 went along, DX became more popular, turning the group from villains to fan favorites. During this time, he adopted an entrance gimmick of asking the crowd "Are you ready? I said, are you ready?", followed by a parody of rival promotion WCW's ring announcer Michael Buffer's famous catch-phrase, "Let's get ready to rumble", substituting the word "rumble" with the DX slogan, "suck it". Also during this time, Triple H began a feud with the leader of the Nation of Domination and rising WWF villain, The Rock.[17] This storyline rivalry eventually led to a feud over the Intercontinental Championship. As part of the feud, Triple H lost the European Championship to Rock's Nation teammate D-Lo Brown on the July 20 episode of Raw is War. Triple H eventually defeated Rock in a ladder match to win his second Intercontinental Championship on August 30 at SummerSlam.[44][17] He did not hold the title long, as he was sidelined with a legitimate knee injury.[17] When The Rock won the WWF Championship on November 15 at Survivor Series,[45] the rivalry between the two continued, as DX fought The Corporation stable of which The Rock was the main star and Triple H received a shot at the WWF Championship on the January 25, 1999 Raw is War in an "I Quit" match, but the match ended when Triple H was forced to quit or see his aide Chyna chokeslammed by Kane.[17] This began a new angle for Triple H, as Chyna betrayed him by attacking him after the match and joining The Corporation.[17]

On March 28 at WrestleMania XV, Triple H lost to Kane after Chyna interfered on his behalf and she was thought to have rejoined DX.[17] Later on in the night, he betrayed his long-time friend and fellow DX member X-Pac by helping Shane McMahon retain the European Championship and joined The Corporation,[17] turning heel in the process. In April, he started to move away from his DX look, taping his fists for matches, sporting new and shorter wrestling trunks and adopting a shorter hairstyle.[17] His gimmick changed as he fought to earn a WWF Championship opportunity.[17] After failed attempts at winning the championship, Triple H and Mankind challenged then WWF Champion Stone Cold Steve Austin to a triple threat match on August 22 at SummerSlam, which featured Jesse "The Body" Ventura as the special guest referee. Mankind won the match by pinning Austin.[46]

The following night on Raw Is War, Triple H defeated Mankind to win his first WWF Championship.[17] He dropped the WWF Championship to Mr. McMahon on the September 16, 1999 episode of SmackDown! before regaining it on September 26 at Unforgiven in a Six-Pack Challenge that included Davey Boy Smith, Big Show, Kane, The Rock and Mankind. He defeated Stone Cold Steve Austin on October 17 at No Mercy before dropping the title to Big Show on November 14 at Survivor Series. Triple H then continued his feud with Mr. McMahon by marrying his daughter Stephanie McMahon and defeating McMahon on December 12 at Armageddon. As a result of the feud, an angle with Triple H and Stephanie began which carried the WWF throughout the next seventeen months; together they were known as The McMahon-Helmsley Faction.[47]

By January 2000, Triple H had dubbed himself "the Game", after stating he was above the top of the wrestling world (as in not merely the "best in the game", but in fact "the game") and was nicknamed "The Cerebral Assassin" by Jim Ross. On the January 3 episode of Raw Is War, Triple H defeated Big Show to win his third WWF Championship.[48]

Triple H feuded with Mick Foley in early 2000. On January 23 at the Royal Rumble, he retained the WWF Championship in a Street Fight after performing two Pedigrees on Foley. The feud ended on February 17 at No Way Out inside Hell in a Cell, where Triple H retained the title and forced Foley to retire.[49] Triple H pinned The Rock at WrestleMania 2000 on April 2 to retain the title,[50] but lost it on April 30 at Backlash to The Rock, ending his reign at 118 days.[51] He regained it three weeks later, in an Iron Man match on May 21 at Judgment Day,[52] only to lose it back to The Rock on June 25 at King of the Ring.[53] Triple H then entered a storyline with Chris Jericho, who upset Triple H by defeating him for the WWF Championship on the April 17 episode of Raw Is War before the title was returned to Triple H because of a fast count made by referee Earl Hebner, and Jericho's reign is not recognized.[54] Their feud culminated in a Last Man Standing match at Fully Loaded on July 23 which Triple H won.[55] He feuded with Kurt Angle, initially over the WWF Championship, but then as a love triangle between himself, Angle, and Stephanie.[56] Both Triple H and Angle wrestled for the WWF Championship against The Rock on August 27 at SummerSlam, but The Rock retained the title after Angle received a legit concussion during a botched Pedigree on a commentary table by Triple H.[57][58] The feud culminated at Unforgiven on September 24, where Triple H defeated Angle with a Pedigree after a low blow from McMahon.[53]

After a brief run as a face that saw him defeat Chris Benoit on October 22 at No Mercy,[59] Triple H reverted to his heel persona and restarted his feud with Stone Cold Steve Austin when it emerged that Triple H had paid off Rikishi to run down Austin at Survivor Series, causing him to take a year off.[60] While Triple H said he had done it in order to shield Austin from the WWF Championship and end his career in storyline, Austin's previous neck injuries started bothering him again in reality, forcing him to have surgery. At Survivor Series on November 19, Triple H and Austin had a match that ended when Triple H tried to trick Austin into coming into the parking lot to run him over again, only to have Austin lift his car up with a forklift and flip the car onto its roof 10 feet high.[61][62] A brutal Three Stages of Hell match between the two at No Way Out on February 25, 2001 saw Triple H defeat Austin 2–1, thus ending their feud.[63] The Three Stages of Hell match received universal acclaim and is widely regarded as one of the most brutal and one of the best professional wrestling match of all times.[64][65] Triple H also feuded with The Undertaker, who defeated him on April 1 at WrestleMania X-Seven.[66] The night after WrestleMania, Triple H interfered in a steel cage match between Austin (who had just won the WWF Championship) and The Rock where he joined forces with Austin and double teamed on The Rock,[67] forming a tag team called The Two-Man Power Trip. Triple H then defeated Chris Jericho for his third Intercontinental Championship on the April 5 SmackDown!,[68] and won it for a fourth time two weeks later by defeating Jeff Hardy.[69] Triple H then became a world tag team champion by winning the WWF Tag Team Championship for the first time at Backlash on April 29 when he and Austin defeated Kane and The Undertaker in a "Winner Take All" tag team match. As Triple H was still Intercontinental Champion, the win made him a double champion. In doing so, Triple H became the seventh Triple Crown winner and second Grand Slam winner in WWE history.[70]

During the main event of the May 21, 2001 episode of Raw Is War, he suffered a legitimate and career-threatening injury.[5][71] He and Austin were defending the WWF Tag Team Championship against Chris Jericho and Chris Benoit. At one point, Jericho had Austin trapped in the Walls of Jericho and Triple H ran in to break it up, but just as he did, he suffered a tear in his left quadriceps muscle,[5][71] causing it to come completely off the bone.[15] Despite his inability to place any weight on his leg, Triple H was able to complete the match.[15] He even allowed Jericho to put him in the Walls of Jericho, a move that places considerable stress on the quadriceps. The tear required an operation, which was performed by orthopedic surgeon Dr. James Andrews. This injury brought an abrupt end to the McMahon-Helmsley Era, as the rigorous rehabilitation process kept Triple H out of action for over eight months,[5][15] completely missing The Invasion storyline.

Triple H after he won the Undisputed WWF Championship at WrestleMania X8

Triple H returned to Raw as a face on January 7, 2002, at Madison Square Garden.[15] He won the Royal Rumble on January 20, receiving an Undisputed WWF Championship match on March 17 at WrestleMania X8,[72] where Triple H defeated Chris Jericho for the Undisputed WWF Championship.[5][72] After holding the title for a month, Triple H lost it to Hollywood Hulk Hogan on April 21 at Backlash.[72] Triple H then became exclusive to the SmackDown! roster due to the WWF draft lottery and continued to feud with Jericho, culminating in a Hell in a Cell match on May 19 at Judgment Day, which Triple H won. On the June 6 episode of SmackDown!, Triple H defeated Hogan in a #1 contender match for the WWE Undisputed Championship at King of the Ring against The Undertaker, but was unsuccessful at the event on June 23.

In the interim, between the Royal Rumble and WrestleMania, the McMahon-Helmsley Faction was brought to an official on-screen conclusion. By the time he returned, Triple H's on-screen marriage to Stephanie McMahon was faltering, so Stephanie faked a pregnancy in order to get him back on her side.[73] When he learned that it was fake, he dumped her publicly on Raw when they were supposed to renew their wedding vows.[73] Stephanie aligned with Jericho afterward,[73] but she was forced to leave after losing a triple threat match on the March 25 episode of Raw when she was pinned by Triple H.[74] The divorce, and thus the storyline, was finalized on July 21 at Vengeance.[75]

Meanwhile, Shawn Michaels had made his return to WWE and joined the New World Order (nWo). Michaels and Kevin Nash planned to bring Triple H over to Raw in order to put him into the group. Mr. McMahon disbanded the nWo following several backstage complications and brought in Eric Bischoff as the Raw general manager. One of Bischoff's first intentions was to follow up on the nWo's plan and bring Triple H over to the Raw roster. Triple H moved to the Raw brand at Vengeance, reuniting with Michaels, but he turned on Michaels by performing a Pedigree on him during what was supposed to be a DX reunion, turning heel once again. The following week, Triple H smashed Michaels' face into a car window to prove that Michaels was weak. These events led to the beginning of a long storyline rivalry between the former partners and an eventual "Unsanctioned Street Fight" on August 25 at SummerSlam, in which Michaels came out of retirement to win. Triple H then attacked him with a sledgehammer and he was carried from the ring on a stretcher.[76]

Before September 2, 2002, WWE recognized only one world champion, the WWE Undisputed Champion, for both the Raw and SmackDown! brands. After SummerSlam, then WWE Undisputed Champion Brock Lesnar became exclusive to the SmackDown! brand, leaving the Raw brand without a world champion. Raw General Manager Eric Bischoff then awarded Triple H the World Heavyweight Championship, represented by the Big Gold Belt (which previously had been used to represent the NWA World Heavyweight Championship and WCW World Heavyweight Championship), making him the first World Heavyweight Champion.[77] Triple H retained his title against Rob Van Dam on September 22 at Unforgiven when Ric Flair hit Van Dam with a sledgehammer.

In October, Triple H began a controversial feud with Kane, leading to a match at No Mercy in which both Kane's Intercontinental Championship and Triple H's World Heavyweight Championship were at stake. In the weeks preceding the match, Triple H claimed that, several years earlier, Kane had an unrequited relationship with a woman named Katie Vick.[78] He went on to claim that, after Vick was killed in a car crash, Kane (the driver) raped her corpse.[78] Triple H later threatened to show video footage of Kane committing the act in question; the footage that finally aired showed Triple H (dressed as Kane) simulating necrophilia with a mannequin in a casket;[78] Kane's tag team partner The Hurricane responded the following week by showing a video of Triple H (rather, someone wearing a Triple H series of masks) getting an enema. The angle was very unpopular with fans,[79] and was de-emphasized before the title match. Triple H went on to defeat Kane at No Mercy on October 20, unifying the two titles.[80]

Triple H eventually lost the World Heavyweight Championship to Shawn Michaels in the first Elimination Chamber match on November 17 at Survivor Series.[81] He defeated Van Dam on the December 2 episode of Raw to earn a title shot at Armageddon with Michaels as the special guest referee. He regained the title from Michaels in a Three Stages of Hell match at Armageddon on December 15, winning 2–1.[81]

Triple H in April 2005

In February 2003, Triple H formed a stable known as Evolution with Ric Flair, Randy Orton, and Batista. The group was heavily pushed on Raw and the height of their dominance occurred after Armageddon, where every member of Evolution left the event holding a title.[82] Triple H held the World Heavyweight Championship for most of 2003, successfully defending against Booker T on March 30 at WrestleMania XIX in an angle with racist undertones.[83] He lost the title after 280 days on September 21 at Unforgiven to Goldberg, in a match with the stipulation that had Goldberg lost, he would have to retire.[84] After failing to win back the title from Goldberg in a rematch on November 16 at Survivor Series, he finally regained the championship from Goldberg in a triple threat match at Armageddon on December 14, which also involved Kane. Triple H fought Shawn Michaels in a Last Man Standing match on January 25, 2004 at the Royal Rumble to a double countout, so he retained the title as a result.[82] Triple H lost the championship to Chris Benoit on March 14 at WrestleMania XX in a triple threat match also involving Michaels.[85] Triple H was drafted to the SmackDown! brand on the March 22 episode of Raw and failed to capture the WWE Championship from Eddie Guerrero.[86] Triple H was traded back to Raw without competing on SmackDown! and tried to reclaim the World Heavyweight title from Benoit in a WrestleMania rematch against Benoit and Michaels on April 18 at Backlash, but was unsuccessful.[85]

At Bad Blood on June 13, Triple H defeated Michaels in the longest Hell in a Cell match in history, ending their feud.[85] He failed to win the title from Benoit on July 11 at Vengeance and on the July 26 episode of Raw in a 60-Minute Iron Man match after interference from Eugene, whom he defeated on August 15 at SummerSlam.[87] The following night on Raw, Triple H turned on his protège Randy Orton (who became the youngest world champion in WWE history at SummerSlam), expressing jealousy over Orton's title victory. He regained the championship from Orton on September 12 at Unforgiven. Following a triple threat World Heavyweight title defense against Benoit and Edge on the November 29 episode of Raw, the World Heavyweight Championship became vacant for the first time.[88] At New Year's Revolution on January 9, 2005, Triple H won an Elimination Chamber match to regain the World Heavyweight Championship after last eliminating Orton, then retained the title against him on January 30 at the Royal Rumble to end their feud. That same night, his stablemate Batista won the Royal Rumble match, earning a world title match at WrestleMania 21. Tension between the two began in the weeks leading up to the event as Triple H convinced Batista to challenge for the WWE Championship instead of his World Heavyweight Championship. On the February 21 episode of Raw, Batista turned on Triple H and signed a contract to face him for the World Heavyweight Championship at WrestleMania.[89] At WrestleMania on April 3, Triple H lost the championship to Batista,[90] and subsequently lost two rematches on May 1 at Backlash[91] and on June 26 at Vengeance, where Batista became the first man to pin Triple H inside Hell in a Cell.[92] After Vengeance, Triple H took a hiatus from WWE due to suffering from minor neck problems.[93]

After a four-month hiatus, Triple H returned to Raw on October 3, where he and Flair defeated Chris Masters and Carlito. After the match, Triple H turned on Flair by attacking him with a sledgehammer, sparking a feud between the duo.[94] Flair defeated Triple H in a steel cage match on November 1 at Taboo Tuesday for Flair's Intercontinental Championship.[95] Subsequently, Triple H defeated Flair in a non-title Last Man Standing match on November 27 at Survivor Series to end their feud.[95]

Triple H failed to win the Royal Rumble match on January 29, 2006 at the Royal Rumble, but another championship opportunity arose for him in the Road to WrestleMania Tournament, which he won, granting him a match for the WWE Championship at WrestleMania 22 on April 2, where he lost to champion John Cena via submission.[96] On April 30 at Backlash, Triple H was involved in another WWE Championship match, fighting Edge and Cena in a triple threat match, where he lost again. Angered at his loss, a bloodied Triple H used his sledgehammer to attack both Edge and Cena and then performed a number of DX crotch chops.[97] Triple H unsuccessfully attempted to win the WWE title from Cena on numerous occasions, blaming his shortcomings on Vince McMahon, which eventually led to a feud between the McMahons and Triple H.

D-X striking their signature pose

Shawn Michaels returned on the June 12 episode of Raw and reunited with Triple H to re-form D-Generation X, turning Triple H face for the first time since 2002.[6] DX defeated The Spirit Squad on June 25 at Vengeance in a 5-on-2 handicap match.[98] They continued their feud with Mr. McMahon, Shane McMahon and The Spirit Squad for several weeks. They then defeated The Spirit Squad again on the July 15, 2006 episode of Saturday Night's Main Event XXXIII in a 5-on-2 elimination match. They then again defeated the McMahons on August 20 at SummerSlam, withstanding the attack of several wrestlers who assaulted them before the match as directed by Mr. McMahon.[97] At Unforgiven on September 17, DX defeated the McMahons and ECW World Champion Big Show in a 3-on-2 handicap Hell in a Cell match. During the match, DX embarrassed Vince by shoving his face in between Big Show's buttocks, and DX won when Triple H broke a sledgehammer over the shoulders of Mr. McMahon after Michaels performed Sweet Chin Music on him.[99]

At Cyber Sunday on November 5, during DX's feud with Rated-RKO (Edge and Randy Orton), special guest referee Eric Bischoff allowed the illegal use of a weapon to give Rated-RKO the win.[99] On November 26 at Survivor Series, DX got their revenge when their team defeated Edge and Orton's team in a clean sweep during their five-on-five elimination match.[100] At New Year's Revolution on January 7, 2007, DX and Rated-RKO fought to a no contest after Triple H suffered a legitimate torn right quadriceps (similar to the one he suffered in 2001 in his other leg) 15 minutes into the match.[101][102] Surgery was successfully performed two days later by Dr. James Andrews.[101]

At SummerSlam on August 26, he defeated King Booker in his return match.[103] On October 7 at No Mercy, Triple H was originally scheduled to face Umaga in a singles match. At the start of the night, Triple H challenged newly named WWE Champion Randy Orton, reigniting their feud that had been interrupted following his injury. Triple H won the match, winning his eleventh world championship and sixth WWE Championship,[104] then defended his title against Umaga in his regularly scheduled match after Mr. McMahon declared the match to be for the WWE title.[105] After that, McMahon gave Orton a rematch against Triple H in a Last Man Standing match in the main event, and Triple H lost after an RKO on a broadcast table.[105] Triple H's title reign at No Mercy is the fifth shortest reign in WWE history, only lasting through the duration of the event.[105] After winning the Raw Elimination Chamber match on February 17, 2008 at No Way Out, Triple H gained a WWE Championship match by outlasting five other men, last eliminating Jeff Hardy after a Pedigree on a steel chair.[106] At WrestleMania XXIV on March 30, Orton retained the title in a triple threat match after punting Triple H and pinning John Cena following Triple H's Pedigree on Cena.[107] On April 27 at Backlash, Triple H won the title in a fatal four-way elimination match against Orton, Cena, and John "Bradshaw" Layfield, tying the record for most WWE Championship reigns with The Rock.[108] Triple H retained the title against Orton on May 18 at Judgment Day in a steel cage match[109] and again on June 1 at One Night Stand in a Last Man Standing match.[110] Orton suffered a legitimate collarbone injury during the match, prematurely ending the feud.[111]

Triple H as WWE Champion in November 2008

On the June 23 episode of Raw, Triple H was drafted to the SmackDown brand as a part of the 2008 WWE draft, in the process making the WWE Championship exclusive to SmackDown.[112] Triple H then went on to defeat John Cena cleanly to retain the WWE Championship on June 29 at Night of Champions.[113] He defended the championship over the summer by defeating the likes of Edge on July 20 at The Great American Bash[114] and The Great Khali on August 17 at SummerSlam,[115] and was the only champion to retain his title at Unforgiven's Championship Scramble matches on September 7.[116] He successfully defended it against Jeff Hardy both on October 5 at No Mercy[117] and Cyber Sunday on October 26.[118]

At Survivor Series on November 23, Triple H was scheduled to defend the title against Vladimir Kozlov and Jeff Hardy, but Hardy was kept out of the match after a scripted attack and injury. During the match, SmackDown general manager Vickie Guerrero announced that Edge had returned and introduced him into the contest. Hardy interfered and hit Triple H with a steel chair meant for Edge, costing him the title after a 210 day reign.[119] After failing to regain the title on December 14 at Armageddon,[120] Triple H entered seventh in the Royal Rumble on January 25, 2009, but was last eliminated by Randy Orton.[121] At No Way Out on February 15, Triple H won the WWE Championship in the SmackDown Elimination Chamber match, setting the record for most reigns at eight.[122] That record stood until 2011 when John Cena won his ninth WWE Championship.[123]

On the February 16 episode of Raw, Triple H made an appearance aiding Stephanie and Shane McMahon, after they were attacked by Randy Orton.[124] On the February 20 episode of SmackDown, Triple H was interviewed by Jim Ross; in the interview, footage was shown highlighting the events that occurred on the February 16 episode of Raw. Ross asked Triple H how he felt seeing that footage, in response, he broke character (after 5 years of marriage) by admitting that Vince McMahon is his father-in-law, that Shane is his brother-in-law, and that Stephanie is his wife, creating a rivalry between Triple H and Orton. On the February 23 episode of Raw, Triple H confronted Orton, before attacking him, Ted DiBiase, and Cody Rhodes (a group known as The Legacy) with a sledgehammer and chasing them from the arena.[125] At WrestleMania 25 on April 5, Triple H defeated Orton to retain the title.[126] On the April 13 episode of Raw, Triple H was drafted back to the Raw brand as part of the 2009 WWE draft.[127] He teamed with Shane McMahon and Batista against Orton and The Legacy in a six-man tag match for the WWE Championship on April 26 at Backlash, which they lost after Orton pinned Triple H.[128] He lost a Three Stages of Hell title match to Orton on June 28 at The Bash.[129] At Night of Champions on July 26, he again lost a title match to Orton in a triple threat match involving John Cena.[130]

On the August 10 episode of Raw, Triple H met with Michaels at an office cafeteria in Texas where Michaels was working as a chef; throughout the show, Triple H tried to convince Michaels to return to WWE from hiatus. After several incidents (including grease grill burgers on fire and Michaels shouting at a little girl), Michaels agreed to team with Triple H to face The Legacy at SummerSlam, superkicked the girl, and quit his chef job.[131] On the August 17 episode of Raw, Triple H and Michaels officially reunited as DX, but as they were in the process of their in-ring promo, The Legacy attacked them both.[132] Their first match after reuniting was against The Legacy at SummerSlam on August 23, which they won.[133] On September 13 at Breaking Point, they lost to The Legacy in the first ever Submissions Count Anywhere match in WWE history.[134]

At Hell in a Cell on October 4, DX defeated The Legacy in a Hell in a Cell match.[135] DX unsuccessfully challenged John Cena for the WWE Championship in a triple threat match on November 22 at Survivor Series,[136] after which they remained friends and partners. On December 13 at TLC: Tables, Ladders and Chairs, DX defeated Jeri-Show (Chris Jericho and Big Show) to win the Unified WWE Tag Team Championship in a Tables, Ladders, and Chairs match.[137]

Triple H at the Tribute to the Troops in December 2010

On December 21, Triple H announced that Hornswoggle was the new DX mascot.[138] This came about after Hornswoggle sued DX for emotional and physical distress due to them not allowing him to join DX.[138] After being taken to court where they were ruled guilty by a jury and judge consisting of dwarves, Michaels told Triple H that Hornswoggle could be the mascot. Triple H agreed to it only if the charges were dropped, which Hornswoggle agreed to.[138] On the January 11, 2010, episode of Raw, Mike Tyson, who was the Raw guest host for the night, teamed with Jericho to face DX; at the end of the bout, Tyson turned on Jericho and aligned himself with Triple H and Michaels.[139] On the February 8 episode of Raw, DX lost the Unified Tag Team Championship to ShoMiz (The Miz and Big Show) in a triple threat elimination tag match, also involving The Straight Edge Society (CM Punk and Luke Gallows). On the March 1 episode of Raw, they lost a rematch for the titles in their last televised match before Michaels retired.[140]

On February 21, Triple H eliminated then WWE Champion Sheamus from the Elimination Chamber match, though he did not win the title. Sheamus attacked him weeks later, setting up a match at WrestleMania XXVI on March 28, which Triple H won.[141] Also at WrestleMania, Michaels lost to The Undertaker and was forced to retire. While giving a farewell speech the next night, Sheamus attacked him and set up a rematch at Extreme Rules on April 25. Sheamus attacked Triple H at the start of the show, before later winning the match, after which Triple H took a long hiatus from the WWE.[142] Triple H made an untelevised appearance on October 30 at the WWE Fan Appreciation Event and also at the 2010 Tribute to the Troops.[143]

On the February 21, 2011 episode of Raw, Triple H returned, interrupting the return of The Undertaker and challenging him to a match at WrestleMania XXVII, which later became a No Holds Barred match. A week later, he attacked Sheamus with a Pedigree through a broadcast table in retaliation for Sheamus giving him a ten-month injury. At WrestleMania XXVII on April 3, Triple H lost, which extended Undertaker's undefeated streak to 19–0; Undertaker was carried from the ring on a stretcher whereas Triple H left on his own accord.[144]

At the end of the July 18 episode of Raw, Triple H returned on behalf of WWE's board of directors to relieve his father-in-law Vince McMahon of his duties.[145] This was followed by the announcement that he had been assigned to take over as Chief Operating Officer (COO) of the WWE. This was during a storyline where CM Punk had won the WWE Championship and left the company. Though a new champion was crowned, Triple H helped re-sign Punk and upheld both championship reigns. He announced he would referee a match to unify both WWE Championships on August 14 at SummerSlam. Although he counted a pinfall for CM Punk to win, John Cena's leg was on the ropes, which would break the pin. Regardless, Triple H's longtime friend Kevin Nash attacked Punk immediately after the match to allow Alberto Del Rio to become the new champion.[146] Though Nash and Punk demanded a match against each other, Triple H fired Nash for insubordination and booked himself in a No Disqualification match on September 18 at Night of Champions with his position of COO on the line.[147] Triple H defeated Punk at Night of Champions despite interference from John Laurinaitis, Nash, The Miz and R-Truth.[148] After repeated attacks from these wrestlers in various matches, the majority of WWE's on-screen staff gave Triple H a vote of no confidence. Mr. McMahon returned to relieve him of his duties on Raw, though he remained the COO. Laurinaitis was named interim general manager of Raw, and booked him and Punk in a tag team match against Miz and R-Truth on October 23 at Vengeance.[149] During the match, Nash once again attacked him (costing Triple H and Punk the match) and did so the following night on the October 24 episode of Raw, hospitalizing him (kayfabe).[150] WWE later announced that Triple H had sustained a fractured vertebra, and would be out of action. He returned on December 12, as part of the Slammy Awards. On December 18, he defeated Nash at TLC: Tables, Ladders, and Chairs in sledgehammer ladder match, after attacking him with a sledgehammer.[151]

Triple H being taunted by The Undertaker ahead of their second consecutive WrestleMania match

Triple H returned on the January 30, 2012 episode of Raw to evaluate Laurinaitis' performance as general manager. Before he could announce the decision, he was interrupted by the returning Undertaker.[152] After initially refusing the rematch as he did not want to tarnish The Undertaker's legacy,[153] Triple H accepted the challenge after being called a coward who lives in Shawn Michaels' shadow, on the condition their rematch be contested inside Hell in a Cell.[154] Triple H went on to lose this match on April 1 at WrestleMania XXVIII.[155]

Triple H returned on the April 30 episode of Raw, when he refused to give in to Brock Lesnar's unreasonable contract demands, resulting in Lesnar attacking him and storyline breaking his arm.[156] Upon his return two weeks later, Triple H was confronted by Lesnar's legal representative, Paul Heyman, who announced Lesnar was filing a lawsuit against WWE for breach of contract. After he accosted Heyman, Heyman threatened another lawsuit against Triple H for assault and battery.[157] At No Way Out on June 17, Triple H challenged a non-present Lesnar to a match at SummerSlam,[158] which Heyman refused on Lesnar's behalf the following night on Raw.[159] At Raw 1000, Stephanie McMahon goaded Heyman into Triple H's challenge against Lesnar.[160] To anger Triple H, Lesnar broke Michaels's arm on the August 13 episode of Raw.[161] Six days later at SummerSlam, Triple H lost to Lesnar after submitting to the Kimura Lock, breaking his arm again in storyline.[162][163]

Triple H returned on the February 25, 2013 episode of Raw, brawling with Brock Lesnar after he attempted to attack Mr. McMahon. The brawl resulted in Lesnar having his head split open and requiring 18 stitches.[164] The following week, Triple H issued a challenge to Lesnar, requesting a rematch with him at WrestleMania 29 on April 7, which Lesnar accepted on the condition that he could choose the stipulation.[165][166] The following week, after Triple H signed the contract and assaulted Heyman, the stipulation was revealed as No Holds Barred with Triple H's career on the line.[167] Triple H defeated Lesnar after a Pedigree onto the steel steps.[168] On May 19 at Extreme Rules, Triple H lost to Lesnar in a steel cage match after interference from Heyman, and also injured his jaw.[169]

The next night on Raw, Triple H wrestled Heyman's newest client, Curtis Axel. He suffered a storyline concussion and was deemed to have forfeited.[170][171][172] Despite being medically cleared to wrestle before the June 3 episode of Raw, Vince and Stephanie McMahon did not allow Triple H to wrestle Axel, citing concerns for his well-being and the safety of his children. In response, Triple H stormed out the arena and vowed to return to the ring the next week on Raw.[173]

Triple H and Stephanie McMahon as The Authority

On August 18 at SummerSlam, Triple H served as the special guest referee for the WWE Championship match between champion John Cena and Daniel Bryan. After Bryan won the match, Triple H attacked him, allowing Randy Orton to cash in his Money in the Bank contract and win the title, turning heel for the first time since 2006.[174] Along with his wife Stephanie, they subsequently created The Authority, with The Shield (Seth Rollins, Roman Reigns and Dean Ambrose) as his enforcers, Kane as the Director of Operations and Orton as their hand-picked WWE Champion.

Triple H making his entrance at WrestleMania XXX

At WrestleMania XXX on April 6, 2014, Triple H lost to Bryan, thereby granting Bryan a part in the subsequent WWE World Heavyweight Championship match against Batista and Orton,[175] which Bryan ultimately won.[176] In order to end Bryan's title reign, Triple H re-formed Evolution with Orton and Batista on the April 18 episode of SmackDown, but Bryan remained champion due to The Shield turning on The Authority. Evolution subsequently lost back-to-back matches with The Shield on May 4 at Extreme Rules[177] and on June 1 at Payback.[178] Batista quit WWE on the Raw after Payback after Triple H refused to grant him his shot at the WWE World Heavyweight Championship. Triple H then went to "Plan B", Seth Rollins, who turned on The Shield and rejoined The Authority.[179]

Triple H making his Terminator Genisys inspired entrance at WrestleMania 31

The Authority were briefly removed from power after losing a five-on-five tag team elimination match on November 23 at Survivor Series after Sting made his WWE debut to assist their opponents.[180] However, The Authority were reinstated on the December 29 episode of Raw after Rollins coaxed Cena into reinstating them by holding Edge hostage.[181] Back in power, Triple H began feuding with Sting, whom he defeated in a no disqualification match on March 29 at WrestleMania 31 after interference from D-Generation X.[182] After his match with Sting, he and Stephanie McMahon were later confronted by The Rock and Ronda Rousey during a promo regarding the record crowd at the event.[183]

The WWE World Heavyweight Championship was vacated after Rollins suffered a legitimate severe knee injury in November 2015 and a tournament to determine a new champion was held at Survivor Series on November 22, which was won by Roman Reigns. Throughout the remainder of 2015, The Authority aligned with Sheamus, who successfully cashed in his Money in the Bank contact immediately after Reign's victory.[184] After Sheamus defeated Reigns at TLC: Tables, Ladders & Chairs on December 13, Reigns viciously attacked Triple H, which resulted in a storyline injury that took him off television. During this hiatus, Reigns regained the championship from Sheamus on the following episode of Raw.[185]

On January 24, 2016, Triple H made his return during the Royal Rumble match for the WWE World Heavyweight Championship as the unannounced 30th entrant. After eliminating Reigns, he then eliminated Dean Ambrose to secure his second Royal Rumble win and 14th (and final) world championship.[186] He successfully defended the championship against Ambrose on March 12 at Roadblock,[187] and defeated Dolph Ziggler in non-title match two days later on Raw, but lost the championship to Reigns in the main event of WrestleMania 32 on April 3, ending his last world championship reign at 70 days.[188] After WrestleMania 32, with The Authority now disbanded, Triple H competed in the WWE Live tour of the United Kingdom in late April before taking a hiatus from WWE television. However, he continued making occasional appearances in an executive role for NXT.[189][190]

On the August 29 episode of Raw, Triple H made his return by interfering in the main event for the recently vacated and established WWE Universal Championship. Firstly, he attacked rival Roman Reigns with a Pedigree, allowing former Authority stable member Seth Rollins to eliminate him, before attacking Rollins with a Pedigree, allowing Kevin Owens to win the title.[191] This began a feud with Rollins, which culminated in a "non-sanctioned match" at WrestleMania 33 on April 2, 2017,[192] where Rollins defeated him.[193]

Triple H with his wife Stephanie McMahon at WrestleMania 34

Despite being part of Kurt Angle's Team Raw on November 19 at Survivor Series, Triple H attacked him and caused him to be eliminated in their match against Team SmackDown, and he ultimately got credit for winning the match after he pinned Shane McMahon of Team SmackDown.[194] Angle subsequently joined forces with the debuting Ronda Rousey, and the two defeated Triple H and Stephanie McMahon in a mixed tag match at WrestleMania 34 on April 8, 2018 after Stephanie submitted to Rousey's armbar.[195]

Triple H turned face again for the first time since 2013 and his final feuds were high-profile rematches with wrestlers that he had previously worked with. On April 27 at the Greatest Royal Rumble in Jeddah, Saudi Arabia, John Cena defeated Triple H in the first match ever featured on a Saudi pay-per-view event.[196] He subsequently defeated The Undertaker on October 6 at Super Show-Down in a match that was billed as the "Last Time Ever".[197] His feud with The Undertaker continued into Crown Jewel on November 2, where Shawn Michaels came out of retirement to reform DX with him, in a winning effort against The Brothers of Destruction (The Undertaker and Kane).[198] At WrestleMania 35 on April 7, 2019, Triple H defeated Batista with assistance from Ric Flair in what was Batista's retirement match.[199] His final match on pay-per-view was a loss to Randy Orton at Super ShowDown on June 7.[200] Triple H's final house show match took place on June 29 in Tokyo, Japan, where he and Shinsuke Nakamura defeated Robert Roode and Samoa Joe in a tag team match after Nakamura pinned Roode.[201]

Triple H's appearances became increasingly sporadic and 2020 became the first year in which he did not wrestle a match since the start of his career. However, he continued to make occasional on-screen appearances in non-wrestling roles, including on the April 24 episode of SmackDown, which was dedicated to his 25th anniversary in WWE.[202] The final match of his career took place on the January 11, 2021 episode of Raw when he faced Randy Orton in an "unsanctioned fight", but after Alexa Bliss and "The Fiend" Bray Wyatt got involved, Alexa Bliss attacked Orton with a fireball causing the match to end in no-contest.[203]

In September 2021, Triple H suffered from heart failure and a defibrillator was installed in his chest.[204] Due to his newly discovered heart condition, Triple H announced his retirement from wrestling during an appearance on First Take on March 25, 2022.[205] On April 3, he introduced the second night of WrestleMania 38 as the COO of WWE, subsequently leaving a microphone and his wrestling boots in the ring to signify his official in-ring retirement.[13] He later expressed a sense of being at peace with his forced retirement, stating that he "did everything [he] wanted to do and then some".[206]

On September 6, 2022, WWE announced that Triple H was promoted to Chief Content Officer of the company.[207] On the October 10 episode of Raw, he, along with Shawn Michaels, X-Pac, and Road Dogg, held a DX reunion to celebrate the stable's 25-year anniversary.[208] The group made an additional appearance at Raw is XXX on January 23, 2023.[209] He made further appearances on both the Raw and SmackDown episodes following WrestleMania 39 to announce the latest WWE Draft. On the April 24 episode of Raw, Triple H unveiled a new World Heavyweight Championship, which was won by Seth Rollins at Night of Champions on May 27. Following the completion of WWE's acquisition by Endeavor on September 12, 2023; Triple H continued to serve as the head of creative for WWE.[210]