Although he was heavily pushed in the first few months after his debut, Helmsley's career stalled during 1996, starting off with being mired in a feud with Duke "The Dumpster" Droese following a loss during the Free for All at 1996 Royal Rumble. Up until that event, his angle included appearing on television each week with a different female valet. Sable was his valet at WrestleMania XII, and after his loss to Ultimate Warrior, as part of the storyline, he took his aggressions out on her. The debuting Marc Mero came to her rescue, starting a feud between the two wrestlers.
During 1996, Helmsley appeared on an episode of WWF Superstars in a match against Marty Garner. When Levesque 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.
Helmsley was known backstage as one of the members of The Kliq, a group of wrestlers including Shawn Michaels, Kevin Nash, Sean Waltman (X-Pac) and Scott Hall, who were known for influencing Vince McMahon and the WWF creative team. 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. Despite the punishment, Helmsley did have several successes following the MSG Incident. Mr. Perfect became his manager and he won the WWF Intercontinental Championship for the first time on October 21, 1996, defeating Marc Mero. 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 belt for nearly four months before dropping it to Rocky Maivia on the February 13, 1997 special edition of Monday Night Raw, called Thursday Raw Thursday. For a very brief time, Helmsley was accompanied by Mr. Hughes, who was his storyline bodyguard. After losing the Intercontinental title, he feuded with Goldust, defeating him at WrestleMania 13. During their feud, Chyna debuted as his new bodyguard.
Helmsley's push resumed in 1997, when he won the 1997 King of the Ring tournament by defeating Mankind in the finals. Later that year, Shawn Michaels, Helmsley, Chyna and Rick Rude formed D-Generation X (DX). This stable later became known for pushing the envelope, as Michaels and Helmsley made risqué promos—spawning the catchphrase "Suck It", using a "crotch chop" hand motion, and sarcastically deriding Bret Hart and Canada. By that point, Helmsley had fully dropped the "blueblood snob" gimmick, appearing in T-shirts and leather. During this period, his ring name was shortened to simply Triple H. Even after the DX versus Hart Foundation storyline ended, Helmsley continued to feud with the sole remaining member Owen Hart over the WWF 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. Helmsley won after Chyna threw powder into Slaughter's eyes, momentarily "blinding" him and allowing her to interfere in the match.
After WrestleMania, Michaels was forced into temporary retirement due to a legitimate back injury sustained at the Royal Rumble, with Triple H taking over the leadership position in DX, 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. As 1998 went along, D-Generation X became more popular, turning the group from villains to fan-favorites. During this time, he began a feud with the leader of the Nation of Domination and rising WWF villain, The Rock. This storyline rivalry eventually led to a feud over the Intercontinental Championship, which Triple H won in a ladder match at SummerSlam. He did not hold the title long, however, as he was sidelined with a legitimate knee injury. When The Rock won the WWF Championship at Survivor Series, the rivalry between the two continued, as DX fought The Corporation stable, of which The Rock was the main star. Triple H received a shot at the WWF Championship on the January 25, 1999 episode of Raw in an "I Quit" match against The Rock, but the match ended when Triple H was forced to quit or see his aide Chyna chokeslammed by Kane. This began a new angle for Triple H, as Chyna betrayed him by attacking him after the match and joining The Corporation.
At WrestleMania XV, Triple H lost to Kane after Chyna interfered on his behalf, and she was thought to have rejoined DX. 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. 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. Levesque's gimmick changed as he fought to earn a WWF title shot. After numerous failed attempts at winning the championship, Triple H and Mankind challenged 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. The following night on Raw, Triple H defeated Mankind to win his first WWF Championship.
Triple H dropped the WWF Championship to Vince 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 Vince McMahon by marrying his daughter, Stephanie McMahon. He then defeated McMahon at Armageddon. As a result of the feud, an angle with Triple H and Stephanie McMahon began which carried the WWF throughout the next seventeen months; together they were known as the "McMahon-Helmsley Faction".
By January 2000, Triple H dubbed himself "The Game," implying that he was on top of the wrestling world and was nicknamed "The Cerebral Assassin" by Jim Ross. On the January 3 episode of Raw is War, Triple H defeated The Big Show to win his third WWF championship.
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 doing two pedigrees on Foley. The storyline would come to an end at No Way Out in a Hell in a Cell where if Mick Foley lost he would have to retire. Triple H retained his title at the PPV and thus ending Mick Foley's fifteen-year career. Triple H pinned The Rock at WrestleMania 2000 to retain the title, but lost it at Backlash to The Rock. He regained it three weeks later, in an Iron Man match at Judgment Day, only to lose it back to The Rock at King of the Ring. Triple H then entered a storyline feud with Chris Jericho, which culminated in a Last Man Standing match at Fully Loaded. 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. On the August 3 episode of SmackDown!, Triple H and his wife, Stephanie McMahon, along with Kurt Angle, were booked in a Six-man tag team match by Commissioner Mick Foley, against the Dudley Boyz (Buh-Buh Ray Dudley and D-Von Dudley), which Triple H, McMahon, and Angle won. After the match, as Triple H left the ring, Angle and McMahon hugged in a victory celebration, frustrating Triple H and marking the beginning of the Triple H-Angle feud. On the August 24 edition of Smackdown!, Angle kissed Stephanie McMahon after she was injured during a tag team match. At SummerSlam, The Rock defeated Triple H and Angle in a Triple Threat match to retain the WWF Championship after Angle received a concussion at the hands of Triple H. Angle had started taking a liking to Triple H's on-screen wife, Stephanie McMahon which made Triple H, jealous of Angle. On August 28 edition of Raw is War, Angle interfered in a match between Eddie Guerrero and Triple H by attacking both men with a chair. On September 11 edition of Raw is War, Angle interfered in Triple H's match with Chris Jericho and distracted Triple H, causing Triple H to leave the ring and chase Angle. Later that night, Angle attacked both Triple H and McMahon after his Handicap match against T & A. The feud would culminate at Unforgiven, where Triple H defeated Angle after a low blow from Stephanie and a Pedigree from Triple H.
A later storyline feud between Triple H and Steve Austin started when it emerged that Triple H had paid off Rikishi to run down Austin at Survivor Series, causing him to take a year off. In storyline, Triple H said he had did 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 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. Triple H returned a few weeks later and attacked Austin. The feud continued into 2001 and ended in a Three Stages of Hell match in which Helmsley defeated Austin. In 2001, Triple H also feuded with The Undertaker, who defeated him at WrestleMania X-Seven. 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, 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 episode of SmackDown!, and won it for a fourth time two weeks later by defeating Jeff Hardy. Triple H then became a tag team champion for the first time at Backlash when he and Austin defeated Kane and The Undertaker in a winner-take-all tag match. As Triple H was still Intercontinental Champion, the win made him a double champion.
During the May 21, 2001 episode of Raw, he suffered a legitimate and career-threatening injury. In the night's main event, he and Austin were defending the Tag Team Championship against Chris Jericho and Chris Benoit. At one point, Jericho had Austin trapped in the Walls of Jericho. Triple H ran in to break it up, but just as he did, he suffered a tear in his left quadriceps muscle, causing it to come completely off the bone. Despite his inability to place any weight on his leg, Triple H was able to complete the match. 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, completely missing The Invasion storyline.
Triple H returned to Raw as a face on January 7, 2002 at Madison Square Garden. He won the Royal Rumble and received an Undisputed WWF Championship match at WrestleMania X8. At WrestleMania X8, Triple H beat Chris Jericho for the Undisputed Championship. After holding the title for a month, Helmsley dropped it to Hulk Hogan at Backlash. 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. On June 6, Triple H defeated Hogan in a Number One Contenders match for the Undisputed Championship at the King of the Ring against The Undertaker but was unsuccessful at the event.
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 on the rocks, so Stephanie faked a pregnancy in order to get him back on her side. When he learned that it was fake, he dumped her publicly on Raw when they were supposed to renew their wedding vows. Stephanie aligned with Jericho afterward, but she was forced to leave after losing a Triple Threat match on Raw the night after WrestleMania when she was pinned by Triple H. The divorce, and thus the storyline, was finalized at Vengeance.
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. Vince McMahon, however, disbanded the nWo following several backstage complications and brought in Eric Bischoff as the Raw brand's new 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 did indeed go to the Raw brand, reuniting with Shawn Michaels, but on July 22 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" 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.
Before September 2, 2002, WWE recognized only one champion for both the Raw and SmackDown! brands. After SummerSlam, champion Brock Lesnar became exclusive to SmackDown!, leaving Raw without a champion. Raw General Manager Eric Bischoff then awarded Triple H the World Heavyweight Championship making him the first World Heavyweight Champion of the WWE brand. Triple H retained his title against Rob Van Dam at Unforgiven when Ric Flair hit RVD with a sledgehammer.
Triple H eventually lost the World Heavyweight Championship to Shawn Michaels in the first Elimination Chamber match, at Survivor Series. He defeated RVD for the title shot at Armageddon with Michaels as special referee. He regained the title from Michaels in a Three Stages of Hell match at Armageddon.
In January 2003, Triple H formed a stable known as Evolution with Ric Flair, Randy Orton, and Batista. Triple H and Ric Flair challenged RVD and Kane for the World Tag Team Titles, but they lost the match. The group was pushed on Raw from 2003 to 2004. The height of their dominance occurred after Armageddon when every member of Evolution left the pay-per-view holding a title. Triple H held the World Heavyweight Championship for most of 2003 until Unforgiven, losing the title to Bill Goldberg. After a failed attempt to win back the title from Goldberg in a rematch at the Survivor Series, he finally regained the championship against Goldberg in a triple threat match at Armageddon which also involved Kane. At the 2004 Royal Rumble, Triple H and Shawn Michaels fought in a Last Man Standing match to a double countout, so Triple H retained the title as a result. Triple H dropped the title to Chris Benoit at WrestleMania XX, and he was unable to reclaim the belt from Benoit in subsequent rematches, including a rematch from WrestleMania between Triple H, Benoit, and Shawn Michaels at Backlash.
He then ended his feud with Michaels, defeating him in a Hell in a Cell match at Bad Blood. After another failed attempt, losing to Benoit at Vengeance, he focused on Eugene, beating him at SummerSlam. Triple H then regained the title from former associate Randy Orton at Unforgiven. Following a Triple Threat World Heavyweight title defense against Benoit and Edge on the November 29, 2004 episode of Raw, the World Heavyweight Championship became vacant for the first time. At New Year's Revolution, Triple H won the Elimination Chamber to begin his tenth world title reign. At WrestleMania 21, Triple H lost the championship to Batista, and subsequently lost two rematches at Backlash and Vengeance. After Vengeance, Triple H took hiatus from WWE due to suffering from his minor neck problems.
After 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. Flair defeated Triple H in a Steel cage match at Taboo Tuesday for Flair's Intercontinental Championship. Subsequently, Triple H defeated Flair in a non-title Last Man Standing match at Survivor Series to end their feud.
Although Triple H failed to win the Royal Rumble match at the Royal Rumble, another championship opportunity arose for Triple H in the Road to WrestleMania Tournament. He won the tournament, granting him a match for the WWE Championship at WrestleMania 22. At WrestleMania, Triple H and John Cena fought in the main event for the title, which Triple H lost via submission. 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. In an act of frustration, a bloodied Triple H used his sledgehammer to attack both Edge and Cena and then performed a number of DX crotch chops. 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 reform D-Generation X, turning Triple H into a fan-favorite once again for the first time since 2002. DX defeated the Spirit Squad at Vengeance in a 5-on-2 handicap match. They continued their feud with Vince McMahon, Shane McMahon and the Spirit Squad for several weeks. They then defeated the Spirit Squad again on the July 18, 2006 episode of Saturday Night's Main Event in a 5-on-2 Elimination match. They then again defeated the McMahons at SummerSlam, withstanding the attack of several handpicked WWE superstars by Vince McMahon. At Unforgiven, D-Generation X overcame the odds once again, defeating The McMahons and ECW World Champion Big Show in a 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 Vince McMahon after Michaels performed Sweet Chin Music on him.
At Cyber Sunday during DX's feud with Rated-RKO, special guest referee Eric Bischoff allowed the illegal use of a weapon to give Rated-RKO the win. At Survivor Series, DX got their revenge when their team defeated Edge and Orton's team in an Elimination Match. In January 2007, at New Year's Revolution, 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 but in the other leg) fifteen minutes into the match. Surgery was successfully performed on January 9, 2007 by Dr. James Andrews.
Triple H made his return at SummerSlam, where he defeated King Booker. 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, and then defended his title against Umaga in his regularly scheduled match after Mr. McMahon declared the match to be for the WWE title. 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 failing to beat the ten count when Orton hit his RKO onto the announcer's table. Triple H's title reign at No Mercy is the fifth shortest reign in WWE history, only lasting through the duration of the event. After winning the Raw Elimination Chamber 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. However, at WrestleMania XXIV, Randy Orton retained after punting Triple H and pinning John Cena following Triple H's Pedigree on Cena. 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. 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. Orton suffered a legitimate collarbone injury during the match, thus ending the feud prematurely.
On June 23, 2008 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. He defended the championship over the summer and was the only champion to retain his title at Unforgiven's Championship Scramble matches. After this he defended it against Jeff Hardy, who was in the Unforgiven match.
At Survivor Series, Triple H was scheduled to defend the championship against Vladimir Kozlov and Hardy, however 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. Jeff Hardy interfered and hit Triple H with a steel chair meant for Edge, thus costing him the title and resulting in Edge winning his sixth World Title. Triple H entered seventh in the 2009 Royal Rumble, but was last eliminated by Randy Orton. In February at Elimination Chamber, Triple H won the WWE Championship in the SmackDown Chamber match, setting the record for most reigns at eight. That record stood until 2011 when John Cena won his ninth WWE Championship.
On the February 16, 2009 episode of Raw, Triple H made an appearance aiding Stephanie and Shane McMahon, after they were attacked by Randy Orton. 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. Weeks later, it was announced that Triple H would defend the WWE championship against Orton at WrestleMania XXV. At the event, Triple H defeated Orton to retain the title.Triple H would later face Orton and Legacy in a six man tag team match with Shane McMahon and Batista for the WWE championship at Backlash (2009). Triple H lost the title after trying to stop Batista from hitting Cody Rhodes with a chair then being hit with a RKO by Orton followed by the running punt to the head, allowing Orton to win the WWE championship and putting Hunter out of action for six weeks. At The Bash, Triple H would lose to Orton in a Three Stages of Hell match for the WWE Title. At Night of Champions, Triple H would again lose to Orton in a match for the WWE Championship, this time in a Triple Threat match, also involving John Cena.
On the August 10, 2009 episode of Raw, video segments aired in which Triple H met with Michaels at an office cafeteria in Texas where he was working as a chef; throughout the segments, Triple H would try to convince Michaels return to WWE from hiatus. After several incidents during the segments (including a grease grill burgers on fire and Shawn shouting at a little girl), Michaels agreed to team with Triple H to face The Legacy at SummerSlam, superkicking the girl, and quitting from his chef job in the process. On the August 17 episode of Raw, in St. Louis, MO, Michaels and Triple H officially reunited as DX, but as they were in the process of their in-ring promo, Legacy attacked them both. Their first match after reuniting was against Legacy at SummerSlam, which they won. At Breaking Point, however, they lost to Legacy in the first ever Submissions Count Anywhere match in WWE history.
At the October pay-per-view Hell in a Cell, DX defeated Legacy in a Hell in a Cell match. DX would challenge John Cena for the WWE Championship in a triple threat match at Survivor Series with both men failing to win the title, although they were able to retain their friendship and tag team partnership. On December 13 at TLC: Tables, Ladders & Chairs, DX defeated Chris Jericho and The Big Show to win the Unified WWE Tag Team Championship in a Tables, Ladders, and Chairs match; the first tag team championship reign for Michaels and Triple H as a tag team.
On December 21, Triple H announced that Hornswoggle was the new DX mascot. This came about after Hornswoggle sued DX for emotional and physical distress due to them not allowing him to join DX. 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. On January 11 Mike Tyson, who was the Raw guest host for the night, teamed with Jericho to face DX; however, at the end of the bout, Tyson turned on Jericho and aligned himself with Michaels and Triple H. On the February 8, 2010 episode of Raw, DX lost their Unified Tag Team Titles to ShoMiz (The Miz and The Big Show) in a Triple Threat Elimination Tag Team match also featuring The Straight Edge Society (CM Punk and Luke Gallows.) On the March 1 episode of Raw they lost their rematch for the titles which would be their last televised match before Michaels retired.
On February 21, Triple H eliminated WWE Champion Sheamus in an Elimination Chamber match, though he would not win the title himself. Sheamus attacked him weeks later, setting up a match between the two at WrestleMania XXVI, where Triple H was victorious. Also at WrestleMania, Shawn Michaels lost to The Undertaker and was forced to retire, but while giving a farewell speech the next night, Sheamus attacked him. This would set up a rematch at Extreme Rules where Sheamus attacked Triple H at the start of the show ahead of a win in their scheduled contest to allow Triple H time off to recover from injuries. Triple H made an untelevised appearance on October 30 at the WWE Fan Appreciation Event and also at the 2010 Tribute to the Troops.
On the February 21, 2011 episode of Raw, Triple H made his return to the WWE by interrupting the return of The Undertaker. He challenged him to a match at WrestleMania XXVII, which later became a No Holds Barred match. A week later he put Sheamus through the announce table with a Pedigree, in retaliation for Sheamus giving him a 10 month injury. At WrestleMania XXVII Triple H lost which extended Undertaker's undefeated streak to 19-0, however Undertaker was carried from the ring in a stretcher whereas Triple H left the ring of his own volition.
At the end of the July 18, 2011 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. 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 resign CM 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 champion. 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. He won the match despite interference from John Laurinaitis, Nash, The Miz and R-Truth. 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 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. During the match, Nash once again attacked him and did so the following night on the October 24 Raw, hospitalizing him. WWE later announced that Triple H sustained a fractured vertebrae which would remove him from television until his return on December 12, as part of the Slammy Awards. On December 18, Triple H defeated Nash at Tables, Ladders, and Chairs in Sledgehammer Ladder Match where he used the sledgehammer against Nash.
Triple H returned on the January 30 edition of Raw, to evaluate Laurinaitis' performance as General Manager. Before he could announce the decision, he was interrupted by the returning Undertaker. After initially refusing the rematch as he did not want to tarnish Undertaker's legacy, 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. Triple H went on to lose this match at WrestleMania XXVIII.
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. 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 acosted Heyman, Heyman threatened another lawsuit against Triple H for assault and battery. At the No Way Out pay-per-view in June, Triple H challenged Lesnar, who was not present, to a match at SummerSlam, which Heyman refused on Lesnar's behalf the following night on Raw. At Raw 1000, Stephanie McMahon managed to goad Heyman into accepting her husbnd's challenge against Lesnar. In a bid to psychologically unsettle Triple H, Lesnar would storyline break the arm of Triple H's best friend Shawn Michaels on the August 13 episode of Raw. Six days later at SummerSlam, Lesnar defeated Triple H via submission after once again breaking his arm. On the August 27 episode of Raw, Triple H was supposed to address his potential retirement, but he did not make a definitive decision as he merely announced he was unsure of his future. WWE portrayed his speech as "an emotional farewell of sorts... seemingly capping his epic in-ring career".
On the February 25, 2013 episode of Raw, Triple H returned, brawling with Brock Lesnar, who was about to attack Vince McMahon for a second time. During the brawl, Lesnar's head was busted open and required 18 stitches. The following week on Raw, Triple H set out a challenge to Lesnar for a match at WrestleMania 29. Brock would later return and take out Triple H's friends, The New-Age Outlaws with two F-5s. Lesnar and Heyman would then announce that Lesnar would face Triple H at Wrestlemania only if he accepts the stipulations laid by Heyman and Lesnar. At March 18th episode of RAW, Triple H would brutally attack Paul Heyman before signing the contract. After signing the contract, Lesnar would come and save Heyman. After being saved, Heyman would announce that Triple H has signed a contract with a stipulation which states that if Triple H loses to Brock Lesnar, it would be the end of his career. Triple H went on to win the match after hitting Lesnar with a Pedigree onto the steel steps. On the April 15 episode of Raw, Lesnar attacked 3MB (Heath Slater, Drew McIntyre, and Jinder Mahal) before Paul Heyman challenged Triple H to face Lesnar in a Steel Cage match at Extreme Rules, which Triple H accepted the following week. Triple H ended up losing the match at the pay-per-view on May 19 thanks to interference from Paul Heyman, where he also injured his jaw. The following night on Raw, Triple H competed in a match against Heyman's newest client, Curtis Axel. He would wind up suffering a concussion (legit), ending the match in a no-contest (though Axel was awarded the win by forfeiture). Despite being medically cleared to wrestle before June 3 episode of Raw, Triple H was not allowed to wrestle Axel as ordered by Vince and Stephanie McMahon due to legitimate concerns about his well-being and the safety of his children; in response, Triple H stormed out the arena and vowed to be back in the ring next week on Raw. Triple H made his return on the 10 June episode of Raw against Curtis Axel, only to be handed a loss by a screwjob by Vince McMahon to award the win to Axel by a dubious disqualification, then McMahon made Axel win by forfeiture, ordered Axel off the ring, then steal the bell and microphone to block any further attempts to restart the match.
On the August 12, 2013 episode of WWE Monday Night Raw, Triple H pedigreed Brad Maddox before Mr. McMahon's announcement to him for being special guest referee for John Cena vs. Daniel Bryan at SummerSlam. On the August 16, 2013 episode of WWE Friday Night Smackdown, Triple H was the referee of Daniel Bryan vs Wade Barrett in a no disqualification match after Wade Barrett hit the referee Brad Maddox with a stick. Mr. McMahon was about to be the referee but suddenly Triple H came with a referee shirt and was the referee. Daniel Bryan won the match via pinfall. At SummerSlam 2013, Triple H was the special referee for the main event between John Cena and Daniel Bryan. Bryan won the match via pinfall thus becoming WWE Champion, and Triple H congratulated him. However, Randy Orton entered the ring to cash in his Money In The Bank briefcase. To the surprise of the audience, Triple H hit the Pedigree on Daniel Bryan and helped Orton win the match and the WWE Championship, therefore turning heel for the first time since 2006. 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 Edition of RAW he was knocked out by Big Show and was carried out by officals out of the arena. At the 2013 Slammy Award Raw special, Triple H immediately Pedigreed Orton after Daniel Bryan shoved the WWE Champion onto Stephanie McMahon, despite Orton's shock. At WrestleMania XXX, Triple H lost to Daniel Bryan and assaulted him post match. Later during the main event, Triple H and Stephanie attempted to prevent Bryan from winning the title and recruited Scott Armstrong as a crooked referee. On the April 18 episode of SmackDown, he announced that Evolution would return and he would team up with Randy Orton and Batista. At Extreme Rules, Evolution lost against The Shield. But Evolution rebounded by gaining a new member in Seth Rollins, who turned on The Shield after Batista quitting the team.
The Authority came to end at Survivor Series in the titular match between John Cena's team and Team Authority. Vince McMahon placed the stipulation that if Team Authority lost, Triple H and Stephanie would be stripped of their power. During the match, Triple H tried to get the last member of Team Cena, Dolph Ziggler, eliminated by attacking two referees and placing Seth Rollins (who was also the final member of Team Authority) on top of Ziggler and calling crooked referee Scott Armstrong into the ring to make the count, when Sting came out and attacked Armstrong and Triple H, costing Team Authority the win. On the December 29 edition of Raw, The Authority was brought back in power by John Cena, and he and his wife entered Raw, stepped on the entrance ramp, celebrating their return with a glass of champagne and a kiss.
On the January 5, 2015 episode of Raw, Triple H and Stephanie would fire Dolph Ziggler, Ryback and Erick Rowan, all members of Team Cena at Survivor Series, during what they dubbed John Cena Appreciation Night. Triple H would allow Cena the chance to win their jobs back over the next several weeks, and on the January 19 episode of Raw, Cena would defeat Rollins, Kane and Big Show in a three-on-one Handicap match when Sting once again appeared, distracting the authority, allowing Cena to roll-up Rollins and win back their jobs. 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, and they confronted each other at the event, in which lead Sting to challenge Triple H for a match at WrestleMania 31, in which Triple H accepted the challenge. He defeated Sting at the event with help from DX. After his match with Sting, he and Stephanie McMahon were later confronted by The Rock and Rhonda Rousey during a promo regarding the record crowd at the event.
Throughout 2015, Triple H maintained his role as the leader of The Authority, and was involved in mediating issues between Seth Rollins and Kane. Over the summer, Triple H began to test Rollins by having him defend the championship against Roman Reigns, Brock Lesnar, John Cena, and Sting.
After Rollins suffered a 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. 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. 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 speared by him. This allowed Sheamus cash in his Money in the Bank contract and quickly defeat Reigns to win the championship, resulting in Sheamus aligning with The Authority.
The Authority made a rematch between Reigns and Sheamus for the title the following night on Raw, with the stipulation that Dean Ambrose and The Usos would lose their 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 Reigns' title reign at Survivor Series.) Reigns won by disqualification, allowing Ambrose and The Usos to keep their title shots. In the following weeks, The Authority would continue to stack the odds against Reigns and interfere with his matches. At the TLC: Tables, Ladders and Chairs pay per view, Sheamus retained the WWE World Heavyweight Championship against Reigns 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.
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. At Fastlane, Roman Reigns defeated Dean Ambrose and Brock Lesnar in a triple threat match to become the #1 contender to the WWE World Heavyweight Championship. The next night on Raw, Triple H would brutally attack Reigns during a match with Sheamus, breaking Reigns' nose in storyline. Triple H was then challenged by Ambrose, whom he deafeated at Roadblock to defend the title, before dropping it back to Reigns – who had become the #1 contender for the WWE World Heavyweight Championship by pinning Dean Ambrose in a triple threat match that also involved Brock Lesnar at Fastlane – at WrestleMania 32, ending his reign at 70 days.
On the August 29 episode of Raw, Triple H made his return to WWE television by interfering in the main event for the WWE Universal Championship, delivering a pedigree to Roman Reigns before turning on Seth Rollins and handing Kevin Owens the win and the newly established title.