Triple H

In early 1992, Levesque began to train as a professional wrestler at Killer Kowalski's school in Malden.[4][17][20] His classmates included fellow future WWF wrestlers Chyna and Perry Saturn. Levesque made his professional debut on March 24, 1992 in Kowalski's promotion, the International Wrestling Federation (IWF), under the name Terra Ryzing. In the match, he defeated Tony Roy.[5] In July 1992, he defeated Mad Dog Richard to win the IWF Heavyweight Championship.[1] Levesque wrestled for various promotions on the East Coast independent circuit until 1994 and during this period he was managed by John Rodeo.[21]

In early 1994, Levesque signed a one-year contract with World Championship Wrestling (WCW).[16][22] 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.[6][23] 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.[24] During this time, he began using his finishing maneuver, the Pedigree. Lévesque had a brief feud with Alex Wright that ended at Starrcade[6] with Wright pinning him.[25] Between late 1994 and early 1995, Lévesque briefly teamed with Lord Steven Regal, whose upper class British persona was similar to Lévesque's character.[23] However, the team was short-lived. Lévesque had previously met with Vince McMahon to discuss jumping to the World Wrestling Federation which did not result in his working for the company. However, after McMahon watched Lévesque's Starrcade match, an employment offer was made and Levesque left for the WWF in January 1995.[26]

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

In a modified version of his gimmick in WCW, Levesque started his WWF career as a "Connecticut Blueblood".[24] According to Levesque, JJ Dillion 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.[27] 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.[28] Helmsley made his WWF pay-per-view debut at SummerSlam, where he defeated Bob Holly.[29] In the fall of 1995, Helmsley began a feud with the hog farmer Henry O. Godwinn, culminating in an infamous Hog Pen match at In Your House 5: Seasons Beatings, where Helmsley was victorious.[30]

Although Helmsley was 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.[31][32] 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).[6] Sable was his valet at WrestleMania XII and after his loss to The Ultimate Warrior,[33] 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.[34]

On June 1, 1996, Helmsley appeared on an episode of Superstars in a match against Marty Garner.[35] 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.[35] Garner sued the WWF, eventually settling out of court and later discussed the incident in an appearance on The Montel Williams Show.[36]

Levesque 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.[31] 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.[37] 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, 1996, defeating Marc Mero.[34][37] 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 Monday Night Raw, called Thursday Raw Thursday.[38] For a very brief time, Helmsley was accompanied by Mr. Hughes, who was his storyline bodyguard reminiscent of Ted DiBiase and Virgil.[39] After losing the Intercontinental title, he feuded with Goldust, defeating him at WrestleMania 13.[40] During their feud, Chyna debuted as his new bodyguard.[41]

Triple H and Chyna in April 1999

Helmsley was being highlighted again in 1997, winning the 1997 King of the Ring tournament by defeating Mankind in the finals.[37][42] Later that year, Shawn Michaels, Helmsley, Chyna and Rick Rude formed D-Generation X (D-X). 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[43]—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, even though he would still be referred for a while as Helmsley from time to time and Hunter for the rest of his career.[37] Even after the D-X versus Hart Foundation storyline ended, he continued to feud with the sole remaining Hart family member Owen over the European Championship. This ended in a match between the two at WrestleMania XIV, 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.[44]

After WrestleMania, Michaels was forced into temporary retirement due to a legitimate back injury sustained at the Royal Rumble,[45] with Triple H taking over the leadership position in D-X,[37] 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.[37][46] As 1998 went along, D-X 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 D-X 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.[18] This storyline rivalry eventually led to a feud over the Intercontinental Championship, which Triple H won in a ladder match at SummerSlam.[18] He did not hold the title long, however, as he was sidelined with a legitimate knee injury.[18] When The Rock won the WWF Championship at Survivor Series,[47] the rivalry between the two continued, as D-X 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.[18] This began a new angle for Triple H, as Chyna betrayed him by attacking him after the match and joining The Corporation.[18]

At WrestleMania XV, Triple H lost to Kane after Chyna interfered on his behalf and she was thought to have rejoined D-X.[18] Later on in the night, he betrayed his long-time friend and fellow D-X member X-Pac by helping Shane McMahon retain the European Championship and joined The Corporation.[18] turning heel in the process. In April, he started to move away from his D-X look, taping his fists for matches, sporting new and shorter wrestling trunks and adopting a shorter hairstyle.[18] His gimmick changed as he fought to earn a WWF Championship opportunity.[18] After failed attempts at winning the championship, Triple H and Mankind challenged then WWF Champion Stone Cold Steve Austin to a triple threat match at SummerSlam, which featured Jesse "The Body" Ventura as the special guest referee. Mankind won the match by pinning Austin.[48] The following night on Raw Is War, Triple H defeated Mankind to win his first WWF Championship.[18] He dropped the WWF Championship to Mr. McMahon on the September 16, 1999 episode of SmackDown! before regaining it 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 at No Mercy before dropping the title to Big Show at Survivor Series. Triple H then continued his feud with Mr. McMahon by marrying his daughter Stephanie McMahon and defeating McMahon 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.[49]

By January 2000, Triple H had dubbed himself "The Game", implying that he was on top of the wrestling world (as in not merely the "best in the game", but that he was 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.[50]

Triple H feuded with Mick Foley in early 2000. They both fought at the Royal Rumble in a Street Fight Match for the WWF Championship, which Triple H won after performing two Pedigrees on Foley. The feud ended at No Way Out in a Hell in a Cell, where Triple H retained the title and forced Foley to retire.[51] Triple H pinned The Rock at WrestleMania 2000 to retain the title,[52] but lost it at Backlash to The Rock, thus ending his reign at 118 days.[53] He regained it three weeks later, in an Iron Man match at Judgment Day,[54] only to lose it back to The Rock at King of the Ring.[55] 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 being recognized.[56] Their feud culminated in a Last Man Standing match at Fully Loaded which was won by Triple H.[57] Afterwards, Triple H entered a feud with Kurt Angle, initially over the WWF Championship, but then as a love triangle between himself, Angle, and Stephanie.[58] Both Triple H and Angle wrestled for the WWF Championship against The Rock 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.[59][60] The feud culminated at Unforgiven, where Triple H defeated Angle with a Pedigree after a low blow from McMahon.[55]

After a brief run as a face that saw him defeating Chris Benoit at No Mercy,[61][62] 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.[63] While in the storyline Triple H said he had done it in order to shield Austin from the WWF Championship and end his career, in reality Austin's previous neck injuries started bothering him again, forcing him to have surgery. In November 2000, Triple H and Austin had a match at Survivor Series 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.[64][65] Triple H returned a few weeks later to attack Austin, and their feud continued into 2001 and ended in a Three Stages of Hell match in which Triple H defeated Austin.[66] In 2001, Triple H also feuded with The Undertaker, who defeated him at WrestleMania X-Seven.[67] 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,[68] 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!,[69] and won it for a fourth time two weeks later by defeating Jeff Hardy.[70] Triple H then became a world tag team champion by winning the WWF Tag Team Championship for the first time at Backlash 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 7th Triple Crown winner and 2nd Grand Slam winner in WWE history.[71]

During the May 21, 2001 episode of Raw Is War, he suffered a legitimate and career-threatening injury.[6][72] In the night's main event, 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,[6][72] causing it to come completely off the bone.[16] Despite his inability to place any weight on his leg, Triple H was able to complete the match.[16] 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,[6][16] completely missing The Invasion storyline.[73]

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.[16] He won the Royal Rumble and received an Undisputed WWF Championship match at WrestleMania X8,[74] where Triple H defeated Chris Jericho for the Undisputed WWF Championship.[6][74] After holding the title for a month, Triple H lost it to Hollywood Hulk Hogan at Backlash.[74] 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 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.[75][76]

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.[77] When he learned that it was fake, he dumped her publicly on Raw when they were supposed to renew their wedding vows.[77] Stephanie aligned with Jericho afterward,[77] 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.[78] The divorce, and thus the storyline, was finalized at Vengeance.[79]

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, however, 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 on July 22 he turned on Michaels by performing a Pedigree on him during what was supposed to be a D-X 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" at SummerSlam, in which Michaels came out of retirement to win. Afterwards, however, Triple H attacked him with a sledgehammer and Michaels was carried out of the ring on a stretcher.[80]

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.[81] Triple H retained his title against Rob Van Dam at Unforgiven when Ric Flair hit Van Dam with a sledgehammer.[82]

In October, Triple H would begin 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.[83] He went on to claim that, after Vick was killed in a car crash, Kane (the driver) raped her corpse.[83] Triple H later threatened to show video footage of Kane committing the act in question; however, the footage that finally aired showed Triple H (dressed as Kane) simulating necrophilia with a mannequin in a casket;[83] 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,[84] and was de-emphasized before the title match. Triple H went on to defeat Kane at No Mercy, unifying the two titles.[85]

Triple H eventually lost the World Heavyweight Championship to Shawn Michaels in the first Elimination Chamber match at Survivor Series.[86] 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, winning 2–1.[86]

In February 2003, Triple H formed a stable known as Evolution with Ric Flair, Randy Orton, and Batista. Triple H and Flair challenged Rob Van Dam and Kane for the World Tag Team Championship, but they lost the match. The group was pushed on Raw from 2003 to 2004 and the height of their dominance occurred after Armageddon, where every member of Evolution left the pay-per-view holding a title.[87] Triple H held the World Heavyweight Championship for most of 2003, successfully defending against Booker T at WrestleMania XIX in an angle with racist undertones.[88] He lost the title after 280 days in September 2003 at Unforgiven to Goldberg, in a match with the stipulation that had Goldberg lost, he would have to retire.[89] After failing to win back the title from Goldberg in a rematch at Survivor Series, he finally regained the championship from Goldberg in a triple threat match at Armageddon which also involved Kane after interference from Evolution. On the December 29 episode of Raw, Triple H defended the World Heavyweight Championship against Shawn Michaels, but the match ended in a double pinfall. The two met in a Last Man Standing rematch at the 2004 Royal Rumble, where both failed to answer the ten count, so Triple H retained the title as a result.[87] Triple H lost the championship to Chris Benoit at WrestleMania XX in a triple threat match also involving Michaels.[90] Triple H was drafted to the SmackDown! brand on March 22 episode of Raw and failed to capture the WWE Championship from Eddie Guerrero.[91] Triple H was drafted 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 at Backlash, but came out unsuccessful.[90]

Triple H in April 2005

He then ended his feud with Michaels, defeating him in a Hell in a Cell match at Bad Blood, which became the longest Hell in a Cell match in history.[90] He then resumed his feud with Benoit, facing him for the title at Vengeance and on the July 26 episode of Raw in a 60-Minute Iron Man match, losing both times after Eugene interfered and hit him with a steel chair. He went on to defeat Eugene at SummerSlam.[92] The following night on Raw, Triple H turned on his protège Randy Orton (who became the youngest world champion in WWE history the night prior at SummerSlam), expressing jealousy over Orton's title victory. He then regained the championship from Orton at Unforgiven after interference from Evolution. At Taboo Tuesday, Shawn Michaels was voted by the fans to challenge Triple H for the World Heavyweight Championship, but Triple H retained after Edge interfered. He then led a team of himself, Batista, Edge, and Snitsky against Orton's team of Orton, Benoit, Chris Jericho, and Maven at Survivor Series in a traditional elimination tag team match, which they lost after Triple H was lastly eliminated by Orton.[93] After a triple threat World Heavyweight Championship defense against Benoit and Edge on the November 29, 2004 episode of Raw ended in a draw, the World Heavyweight Championship became vacant for the first time.[94] At New Year's Revolution, Triple H won an Elimination Chamber match to regain the World Heavyweight Championship after last eliminating Orton following interference from Evolution, then defeated Orton at the Royal Rumble to retain the title and end their feud. Also that same night, his stablemate Batista won the 2005 Royal Rumble match, thus earning a world title match at WrestleMania 21. Tension between Triple H and Batista began in the weeks leading up to the pay-per view as Triple H tried to convince Batista to challenge for the WWE Championship at WrestleMania 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.[95] At WrestleMania, Triple H lost the championship to Batista,[96] and subsequently lost two rematches at Backlash and Vengeance in a Hell in a Cell match at the latter event (where Batista became the first man to pin Triple H inside the Cell).[97][98] After Vengeance, Triple H took a hiatus from WWE due to suffering from minor neck problems.[99]

After a four-month hiatus, Triple H returned to Raw on October 3, 2005 as part of WWE Homecoming. He teamed with fellow Evolution member Flair to defeat Chris Masters and Carlito. After the match, Triple H turned on Flair hitting Flair with a sledgehammer, sparking a feud between the duo.[100] Flair defeated Triple H in a steel cage match at Taboo Tuesday for Flair's Intercontinental Championship.[101] Subsequently, Triple H defeated Flair in a non-title Last Man Standing match at Survivor Series to end their feud.[101]

D-X striking their signature pose

By this time Triple H started to act like a tweener, as he began to get cheers by live audience. Although Triple H failed to win the Royal Rumble match at the Royal Rumble, another championship opportunity arose for him in the Road to WrestleMania Tournament. He won the tournament, granting him a match for the WWE Championship at WrestleMania 22, where Triple H and John Cena fought in the main event for the title, which Triple H lost via submission. In this match Cena was booed by the crowd, while Triple H got heavily cheered.[102] Later that month 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 D-X crotch chops.[103] 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.

Shawn Michaels returned on the June 12 episode of Raw and soon reunited with Triple H to re-form D-Generation X, turning Triple H into a fan favorite once again for the first time since mid-2002.[7] D-X defeated The Spirit Squad at Vengeance in a 5-on-2 handicap match.[104] 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 at SummerSlam, withstanding the attack of several wrestlers who assaulted them before the match as directed by Mr. McMahon.[103] At Unforgiven, D-Generation X then defeated the McMahons and ECW World Champion Big Show in a 3-on-2 handicap Hell in a Cell match. During the match, D-X embarrassed Vince by shoving his face in between Big Show's buttocks, and D-X won when Triple H broke a sledgehammer over the shoulders of Mr. McMahon after Michaels performed a Sweet Chin Music on him.[105]

At Cyber Sunday during D-X's feud with Rated-RKO, special guest referee Eric Bischoff allowed the illegal use of a weapon to give Rated-RKO the win.[105] At Survivor Series, D-X got their revenge when their team defeated Edge and Orton's team in a clean sweep during their five-on-five elimination match.[106] In January 2007, at New Year's Revolution, D-X 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.[107][108] Surgery was successfully performed on January 9, 2007 by Dr. James Andrews.[107]

Triple H as WWE Champion in November 2008

Triple H made his return at SummerSlam, where he defeated King Booker.[109] Two months later at No Mercy, Triple H was originally scheduled to face Umaga in a singles match. However, at the start of the night, Triple H decided to challenge newly named WWE Champion Randy Orton, reigniting his rivalry with Orton that had been interrupted following his injury. Triple H won the match, winning his eleventh world championship and sixth WWE Championship,[110] and then defended his title against Umaga in his regularly scheduled match after Mr. McMahon declared the match to be for the WWE title.[111] 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.[111] Triple H's title reign at No Mercy is the fifth shortest reign in WWE history, only lasting through the duration of the event.[111] After winning the Raw Elimination Chamber match 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.[112] However, at WrestleMania XXIV, Orton retained after punting Triple H and pinning John Cena following Triple H's Pedigree on Cena.[113] A month later, 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.[114] Triple H then retained the title against Orton at Judgment Day in a steel cage match and again at One Night Stand in a Last Man Standing match.[115][116] Orton suffered a legitimate collarbone injury during the match, thus ending the feud prematurely.[117]

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.[118] Triple H then went on to defeat John Cena cleanly to retain the WWE Championship at Night of Champions.[119] He defended the championship over the summer by defeating the likes of Edge at The Great American Bash[120] and The Great Khali at SummerSlam,[121] and was the only champion to retain his title at Unforgiven's Championship Scramble matches.[122] After this, he successfully defended it against Jeff Hardy both at No Mercy[123] and Cyber Sunday.[124]

At Survivor Series, Triple H was scheduled to defend the championship 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, thus costing him the title after a 210 days reign and resulting in Edge winning his sixth world title.[125] After failing to regain the title at Armageddon,[126] Triple H entered seventh in the 2009 Royal Rumble, but was last eliminated by Randy Orton.[127] In February at No Way Out, Triple H won the WWE Championship in the SmackDown Elimination Chamber match, setting the record for most reigns at eight.[128] That record stood until 2011 when John Cena won his ninth WWE Championship.[129]

On the February 16 episode of Raw, Triple H made an appearance aiding Stephanie and Shane McMahon, after they were attacked by Randy Orton.[130] 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, thus 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.[131] At WrestleMania 25, Triple H defeated Orton to retain the title. He teamed with Shane McMahon and Batista against Orton and The Legacy in a six-man tag match for the WWE Championship at Backlash, which they lost after Orton pinned Triple H following a Punt Kick. After six weeks off of television, selling the injury, he lost a Three Stages of Hell title match to Orton at The Bash. At Night of Champions, he again lost a title match to Orton in a triple threat match also involving John Cena.[132]

Triple H at the Tribute to the Troops in December 2010

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.[133] On the August 17 episode of Raw, Triple H and Michaels officially reunited as D-X, but as they were in the process of their in-ring promo, The Legacy attacked them both.[134] Their first match after reuniting was against The Legacy at SummerSlam, which they won.[135] At Breaking Point, however, they lost to The Legacy in the first ever Submissions Count Anywhere match in WWE history.[136]

At Hell in a Cell, D-X defeated The Legacy in a Hell in a Cell match.[137] D-X unsuccessfully challenged John Cena for the WWE Championship in a triple threat match at Survivor Series,[138] after which they remained friends and partners. On December 13 at TLC: Tables, Ladders and Chairs, D-X defeated Jeri-Show (Chris Jericho and Big Show) to win the Unified WWE Tag Team Championship in a Tables, Ladders, and Chairs match.[139] This was their first tag team championship reign together.[140]

On December 21, Triple H announced that Hornswoggle was the new D-X mascot.[141] This came about after Hornswoggle sued D-X for emotional and physical distress due to them not allowing him to join D-X.[141] 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.[141] On January 11, 2010 episode of Raw, Mike Tyson, who was the Raw guest host for the night, teamed with Jericho to face D-X; however, at the end of the bout, Tyson turned on Jericho and aligned himself with Triple H and Michaels.[142] On the February 8 episode of Raw, D-X 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 title. This was their last televised match before Michaels retired.[143]

On February 21, Triple H eliminated then WWE Champion Sheamus from the Elimination Chamber match, though he did not win the title himself. Sheamus attacked him weeks later, setting up a match at WrestleMania XXVI, which Triple H won.[144][145] 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. Sheamus attacked Triple H at the start of the show, before later winning the match. Triple H then took time off to recover from injuries.[146] Triple H made an untelevized appearance on October 30 at the WWE Fan Appreciation Event and also at the 2010 Tribute to the Troops.[147]

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

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, 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.[148]

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.[149] 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 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.[150] Though Nash and Punk demanded a match against each other, Triple H fired Nash for insubordination and booked himself in a No Disqualification match at Night of Champions with his position of COO on the line.[151] Triple H defeated Punk at Night of Champions despite interference from John Laurinaitis, Nash, The Miz and R-Truth.[152] 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. He was replaced as general manager of Raw by Laurinaitis, who booked him in a tag team match against Miz and R-Truth at Vengeance.[153] 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).[154] 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 Tables, Ladders, and Chairs in sledgehammer ladder match, after attacking him with a sledgehammer.[155]

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.[156] After initially refusing the rematch as he did not want to tarnish The Undertaker's legacy,[157] 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.[158] Triple H went on to lose this match at WrestleMania XXVIII.[159]

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.[160][161] 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.[162] At No Way Out in June, Triple H challenged Lesnar, who was not present, to a match at SummerSlam,[163] which Heyman refused on Lesnar's behalf the following night on Raw.[164] At Raw 1000, Stephanie McMahon goaded Heyman into Triple H's challenge against Lesnar.[165] To anger Triple H, Lesnar broke Michaels's arm on the August 13 episode of Raw.[166] Six days later at SummerSlam, Triple H lost to Lesnar after submitting to the Kimura Lock, breaking his arm again in storyline.[167][168]

On the August 27 episode of Raw, Triple H was supposed to address his potential retirement, but did not make a definitive decision.[169] On the December 17 episode of Raw, Triple H made a non-wrestling appearance for the 2012 Slammy Awards debuting with his new haircut.[170]

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.[171] The following week, Triple H issued a challenge to Lesnar, requesting a rematch with him at WrestleMania 29, which Lesnar accepted on the condition that he could choose the stipulation.[172][173] 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.[174] At WrestleMania, Triple H defeated Lesnar after a Pedigree onto the steel steps.[175] On the April 15 episode of Raw, Heyman challenged Triple H to face Lesnar in a steel cage match at Extreme Rules,[176] which Triple H accepted the following week.[177] Triple H ended up losing the match at Extreme Rules on May 19 thanks to interference from Heyman, and he also injured his jaw.[178]

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.[179][180][181] 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.[182] On that episode, he lost to Axel when McMahon dubiously disqualified him, ordered Axel to leave the ring, then stole the bell and microphone to prevent the match from being restarted.[183]

Triple H and Stephanie McMahon as The Authority

On the August 12 episode of Raw, Triple H announced that he would be the special guest referee of the SummerSlam main event: the WWE Championship match between champion John Cena and Daniel Bryan before attacking Brad Maddox with a Pedigree. At SummerSlam, after Bryan won the match and the title, Triple H attacked Bryan with a Pedigree, allowing Randy Orton to cash in his Money in the Bank contract and win the title, turning heel for the first time since 2006.[184] Along with his wife Stephanie, they created The Authority, with The Shield as his enforcers and later Kane joining as the Director of Operations.[185]

Over the coming weeks he set up handicap matches against any wrestlers who questioned his decisions, such as Big Show and Dolph Ziggler, even firing Cody Rhodes in retaliation for the latter's insolence. On the October 7 episode of Raw, after "firing" Big Show, Show knocked him out in retaliation and was carried out by officials out of the arena.[186] At the 2013 Slammy Awards, Triple H immediately performed a Pedigree on Orton after Bryan shoved him into Stephanie McMahon, despite Orton's shock.[187]

At WrestleMania XXX, Triple H lost to Bryan, thereby granting Bryan a part in the subsequent WWE World Heavyweight Championship match against Batista and champion Randy Orton. Triple H assaulted Bryan after the match and later attempted to prevent Bryan from winning the title by interfering and recruiting Scott Armstrong as a crooked referee, but these attempts were unsuccessful as Bryan won the title by making Batista submit. 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. At Extreme Rules, Evolution lost to The Shield and again at Payback in a No Holds Barred elimination match.[188] On the June 2 episode of Raw, Batista would leave Evolution and quit WWE after Triple H refused to grant him his shot at the WWE World Heavyweight Championship. Triple H would then resort to "Plan B", which would be Seth Rollins turning on The Shield and rejoining The Authority.[189]

On the October 27 episode of Raw, Triple H would offer John Cena a chance to join forces with The Authority, which Cena refused. This led to Triple H announcing a five-on-five tag team elimination match for Survivor Series, with a team representing The Authority facing a team captained by Cena.[190] On the November 3 episode of Raw, Mr. McMahon announced that if Team Authority would lose, they would be removed from power.[191] On the November 21 episode of SmackDown, Triple H announced that if Team Cena lost, all of Team Cena, except Cena himself, would be fired.[192] At Survivor Series, Big Show joined The Authority by betraying Cena, but Sting made his WWE debut, attacking crooked referee Scott Armstrong and Triple H, and assisted Dolph Ziggler in pinning Rollins to give Team Cena the victory, putting the Authority out of power.[193]

Triple H's entrance at WrestleMania XXX

After being out of power for a month, Rollins coaxed Cena into reinstating The Authority on the December 29 episode of Raw, by holding Raw guest host Edge hostage with Big Show.[194] On the January 19 episode of Raw, Cena would defeat Rollins, Kane and Big Show in a handicap match when Sting distracted The Authority, allowing Cena to pin Rollins and win back the jobs of Ziggler, Ryback and Erick Rowan, who had been fired two weeks previously by Triple H and Stephanie. On January 26, it was officially announced via WWE.com that Triple H challenged Sting to a "face-to-face" confrontation at Fastlane, which Sting accepted; at the confrontation, Sting challenged Triple H to a match at WrestleMania 31, which Triple H accepted.[195] At WrestleMania, Triple H defeated Sting with interference from D-Generation X, but shook hands with Sting after the match. 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.[196][197]

Throughout 2015, Triple H maintained his role as the leader of The Authority, and was involved in mediating issues between Seth Rollins and Kane.[198][199] Over the summer, Triple H began to test Rollins by having him defend the WWE World Heavyweight Championship against Roman Reigns, Brock Lesnar, John Cena, and Sting.[200][201][202][203]

After Rollins suffered a legitimate severe knee injury at a live event, the WWE World Heavyweight Championship was vacated and it was announced that there would be a tournament to determine a new champion at Survivor Series.[204][205] On the November 9 episode of Raw, Triple H offered to give Reigns a bye to the finals of the tournament if he joined The Authority, but Reigns refused.[206] At Survivor Series, Reigns defeated Dean Ambrose in the tournament finals to become WWE World Heavyweight Champion. Triple H came out and attempted to congratulate Reigns, but was instead hit with a spear. This allowed Sheamus to cash in his Money in the Bank contract and quickly defeat Reigns to win the championship, resulting in Sheamus aligning with The Authority.[207]

Triple H making his Terminator Genisys inspired entrance at WrestleMania 31 2015

The Authority made a rematch between Reigns and Sheamus for the title on the November 30 episode of Raw, with the stipulation that Dean Ambrose and The Usos would lose their respective WWE Intercontinental Championship and WWE Tag Team Championship title shots if Reigns failed to win the match in under 5 minutes and 15 seconds (which was the length of Reigns' title reign at Survivor Series); Reigns won by disqualification, allowing Ambrose and The Usos to keep their title shots.[208] At TLC: Tables, Ladders & Chairs, Sheamus retained the WWE World Heavyweight Championship against Reigns in a Tables, Ladders, and Chairs match due to interference from The League of Nations. After the match, Reigns "snapped" and viciously attacked Sheamus as well as Triple H, who had come to calm Reigns. Due to the injuries (kayfabe) suffered from Reigns, Triple H took a hiatus from television.[209]

Triple H in April 2016

Triple H returned at the 2016 Royal Rumble match for the WWE World Heavyweight Championship, as the unannounced 30th entrant. After eliminating the defending champion, Roman Reigns, he then eliminated Dean Ambrose to secure his second Royal Rumble win and 14th world championship overall.[210] After breaking Reigns' nose in storyline in which he received a massive ovation,[211] Triple H was then challenged by Ambrose,[212] whom he defeated at Roadblock to defend the title,[213] before dropping it back to Reigns – who had become the #1 contender for the WWE World Heavyweight Championship by defeating Dean Ambrose and Brock Lesnar in a triple threat match at Fastlane[214] – at WrestleMania 32, ending his reign at 70 days.[215]

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, whilst occasionally appearing at NXT and Cruiserweight Classic events. He was present for the finales of the Cruiserweight Classic and the United Kingdom Championship Tournament, awarding the titles to T.J. Perkins[216] and Tyler Bate, respectively.[217]

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.[218] Triple H appeared at Clash of Champions on September 25, escorting his wife Stephanie McMahon from the building, after Owens successfully defended the Universal Championship against Rollins. On the January 23, 2017 episode of Raw, in a match between Rollins and Sami Zayn, Triple H's music hit, providing the distraction which led to Zayn defeating Rollins and, in the process, stealing Rollins' place in the Royal Rumble.[219] On January 28 at NXT TakeOver: San Antonio, Rollins would "takeover" the show and called out Triple H, who appeared and summoned security guards to escort Rollins out of the arena.[220] On January 30, Triple H made his first appearance on Raw since August 2016, supposedly to finally accept Rollins' challenge for a match. However, he did not, labeling Rollins as an abject failure, despite all the chances he was given. He called Rollins out to come and meet his destroyer, which he does so, only for him to be jumped by Samoa Joe.[221] Rollins suffered a legitimate knee injury in the ambush, casting doubt over the potential match with Triple H,[222] which led to a non-sanctioned match at WrestleMania 33 on April 2,[223] where Triple H lost to Rollins.[224]

On the November 13 episode of Raw, Triple H announced himself as the fifth member of Team Raw for Survivor Series.[225] At Survivor Series, team captain Kurt Angle was about to win the match for Team Raw but Triple H pedigreed Angle which also led to Angle's elimination in the match. However, Triple H later himself pinned Shane McMahon, the final member of Team SmackDown as it appeared Triple H wanted the credit for Team Raw's victory. After the match fellow sole survivor Braun Strowman powerslammed him twice. He was also seen hitting the video screen as he exited the stage.[226][227] Triple H appeared the following night on Raw, and Angle said that if Triple H were to ever attack him again, he would retaliate.[228]

Triple H with his wife Stephanie McMahon at WrestleMania 34

Triple H's next appearance came at the 2018 Elimination Chamber event for the Raw contract signing of Ronda Rousey. During the segment, Triple H confirmed that there were no special stipulations in Rousey's contract, but she would have her debut match at WrestleMania 34. Before Rousey signed her contract, Kurt Angle brought up the incident from WrestleMania 31 where Rousey embarrassed The Authority and said that Triple H and Stephanie were now glad to own Rousey so they could manipulate her. This led to Rousey putting Triple H through a table and Stephanie slapped Rousey. Stephanie then retreated and Rousey signed the contract. The next night, the four had a segment to apologize and it ended with Triple H attacking Angle. The following week, Angle revealed that although Triple H and Stephanie were WWE executives, they also had contracts to compete as wrestlers. Angle reminded Triple H of his warning from after Survivor Series, and he scheduled himself and Rousey to face Triple H and Stephanie at WrestleMania 34 in a mixed tag team match. At WrestleMania, Triple H and Stephanie lost to Angle and Rousey after Stephanie submitted to Rousey's armbar.[229] Triple H lost to John Cena at the Greatest Royal Rumble in Jeddah, Saudi Arabia.[230]

Triple H begin to show signs of a face turn as he returned on the July 23 episode of Raw alongside Stephanie and Vince McMahon to announce the first ever all women's pay-per-view event, WWE Evolution.[231] Following the announcement, it was also announced Triple H would return to in-ring competition at WWE Super Show-Down to take on renowned nemesis, The Undertaker, one last time. On the August 20 episode of Raw, Triple H returned and spoke about how he reluctantly accepted the rematch as the last match between the two at WrestleMania XXVIII (a Hell in a Cell match with Shawn Michaels as special guest referee) was billed as the "End of an Era". Triple H added that the tagline of this contest would be "Last Time Ever".[232] At Super Show-Down, Triple H defeated The Undertaker. After the match Triple H finally turned face for the first time since 2013, as he and Michaels showed respect for The Undertaker and Kane, as they embraced with each other. However the Undertaker and Kane would then proceed to attack them.[233] On the October 8 episode of Raw, Triple H and Michaels announced they would reunite D-X, to face The Brothers of Destruction at Crown Jewel. At Crown Jewel, they defeated the Brothers of Destruction, at the cost of Triple H tearing his pectoral muscles.[234] On the February 25 edition of Raw, Batista returned and attacked Ric Flair backstage as Flair was about to make an entrance for his birthday celebration and called out Triple H.[235] On March 11's edition of Raw Batista challenged Triple H for a match at WrestleMania 35 which Triple H accepted and made it a No Holds Barred match. At WrestleMania, Triple H defeated Batista with assistance from Flair.[236] Triple H lost to Randy Orton in a match at Super ShowDown.[237]

On the November 1 episode of SmackDown, Triple H and Shawn Michaels commandeered an invasion with NXT wrestlers, which started with Shayna Baszler attacking SmackDown Women's Champion Bayley, Sasha Banks and Nikki Cross, followed by Matt Riddle and Keith Lee attacking Sami Zayn, Rhea Ripley and Tegan Nox defeating Mandy Rose and Sonya Deville, Tommaso Ciampa defeating The Miz, and finished with Adam Cole successfully retaining the NXT Championship against Daniel Bryan in the main-event. After the match, Triple H and the rest of the NXT roster stormed the ring and declared war on both Raw and SmackDown, and vowed to win the Survivor Series brand warfare.[238][239] However, at Survivor Series, Team NXT was defeated by Team SmackDown.[240]

The April 24, 2020 episode of SmackDown was dedicated to Triple H's 25th anniversary in WWE.[241]

On November 22, 2020 he made an appearance at Survivor Series during The Undertaker's retirement ceremony.[242]