On the November 29, 1999 episode of Raw is War, WWF owner Mr. McMahon's daughter Stephanie was set to marry Test, but Triple H interrupted the ceremony. He played a video on the titantron showing himself marrying a drugged Stephanie at a drive-through chapel in Las Vegas. This led to a match at Armageddon between Triple H and Mr. McMahon with the stipulations being that if Triple H won, he would receive a WWF Championship title shot on Raw is War, whereas, if Vince was victorious, Triple H would sign an annulment. Triple H won the match, and afterwards, Stephanie turned on her father and hugged her new husband.
The next night on Raw is War, Triple H announced the inception of the McMahon-Helmsley Era. His capture of the WWF Championship soon thereafter, coupled with Road Dogg and Billy Gunn's dominance of the tag team division helped cement the faction's power. With Vince injured and Linda and Shane McMahon absent, Stephanie was the sole remaining shareholder, so she and Triple H assumed control of the WWF.
Principally, the faction ensured that Triple H did not lose the WWF Championship. The faction would therefore interfere in title matches where Triple H might lose, either intentionally causing a disqualification or attacking Triple H's opponent behind the referee's back. The group also helped Stephanie McMahon win and retain the Women's Championship, and assisted X-Pac in his ongoing feud against Kane.
Mid-card and lower card Superstars such as Jeff Hardy became targets for the group, in order to protect the New Age Outlaws' WWF Tag Team Championship. Matt Hardy had been previously injured, so the group made it their mission to cripple him so that the both of them would be injured. Others such as Big Show, Test, Rikishi, Kane, Chris Benoit (an on-and-off ally of the faction), Funaki, Too Cool, and Edge and Christian (before the duo turned heel) were also targets of the faction.
The group was immediately opposed by Mankind, who appeared on Raw is War to tell Triple H and Stephanie that he thought that "the McMahon-Helmsley Era kinda sucks". The Rock would come to his defense, but Triple H forced them to face each other in a "Pink Slip on a Pole" match, where the loser would be fired. The Rock won the match and Mankind was fired. The Faction also tried to get The Rock fired as well, but their efforts failed.
On the January 10, 2000 episode of Raw is War, The Rock and most of the WWF locker room surrounded the ring and threatened to "walk out on Triple H's candy ass" if Mankind was not reinstated. With their backs against the wall, Stephanie and Triple H had no other choice but to comply, leading to Mankind being reinstated and challenging Triple H to a match for the WWF Championship at the Royal Rumble. After a brutal beatdown at the hands of Triple H on the January 10 episode of Raw is War, Mankind metamorphosed into Cactus Jack three days later on SmackDown!, therefore making the match at the Royal Rumble Triple H versus Cactus Jack in a street fight, which was won by Triple H. At No Way Out, Jack lost a Hell in a Cell match to Triple H in which his career was on the line against Triple H's WWF Championship, and therefore Jack was forced to retire.
Meanwhile, The Rock was defeated by Big Show after interference from a returning Shane McMahon, losing his WrestleMania 2000 title shot to Big Show. The Rock then challenged Big Show to a rematch to regain his title shot with Shane McMahon as the special guest referee. The Rock, who had put his career on the line as a stipulation from within the match itself was victorious after a returning Mr. McMahon, who had punched out both Shane and Triple H (who had attempted to intercept Vince on his way to the ring) gave the pinfall victory in The Rock's favor after donning the referee shirt. Linda McMahon then brought Mick Foley out of retirement and made the WrestleMania 2000 main event a fatal four-way elimination match between The Rock, Big Show, Triple H and Mick Foley, with each competitor having a McMahon in his corner. Vince turned on The Rock and secured a victory for Triple H after Big Show and Mick Foley were eliminated. Vince claimed that backing Triple H was the only way to reconcile with his daughter, and accepted Triple H as his son-in-law. He also claimed that The Rock only cared about himself. Shane abandoned Big Show soon after, also backing Triple H.
Over the course of the next few months, the McMahon–Helmsley Faction faced opposition from a variety of wrestlers, including The Rock, Stone Cold Steve Austin, The Undertaker, Kane, Big Show, The Dudley Boyz, Chris Jericho, Too Cool (Scotty Too Hotty, Grand Master Sexay and Rikishi) and Steve Blackman. In addition to the wrestlers, senior referee Earl Hebner had also gotten involved in the opposition against the Faction stemming from his actions during the April 17, 2000 episode of Raw is War, in which Hebner, who had served as the impromptu referee during the Triple H versus Chris Jericho WWF Championship match had counted the pinfall victory for Jericho, enabling the latter to win the championship, though Hebner would later reverse his decision under pressure from Triple H, Stephanie, and Shane, leading to Hebner being fired by Triple H soon afterwards. Mick Foley became WWF Commissioner in mid-2000 and aided in the fight against the Faction as well. Lastly, announcers Jim Ross and Michael Cole were vocal critics of the Faction.
Triple H was a dominant champion throughout the first half of 2000, but lost the WWF Championship to The Rock twice, and had a close call against Chris Jericho as already mentioned before. The first loss was at Backlash, when Stone Cold Steve Austin knocked him out with a chair shot and Linda McMahon reinstated Earl Hebner to count the pinfall. His second loss was at King of the Ring, when he, Vince and Shane defended the title in a six-man tag match against Kane, The Undertaker and The Rock. Vince had hoped that his enemies' individual title aspirations would lead them to fight amongst one another, allowing him to divide and conquer, but his plans were foiled when The Rock pinned Vince for the victory.
After Triple H lost the title, he would feud with Chris Jericho, with the remaining members of D-Generation X by his side. Shane went on to form a short-lived stable with former Faction allies Kurt Angle, Chris Benoit, Big Show, Edge and Christian, known unofficially as The Conspiracy. These allies would help Shane capture the Hardcore Championship from Steve Blackman. Triple H, Shane, Stephanie, and Kurt Angle formed an alliance to win the WWF Championship from The Rock, but this alliance would crumble after a love triangle between Triple H, Stephanie, and Angle.
Stone Cold Steve Austin's return in September 2000 further aided in the dismantling of the group. By late 2000, with Road Dogg out of the WWF, Billy Gunn returning as a face and X-Pac injured, the group was largely forgotten. However, the following year saw Austin turn heel and join Triple H and Mr. McMahon to form The Power Trip, with Stephanie siding with them. On May 21, 2001, Triple H was sidelined by a tear in his left quadriceps muscle, which kept him out of action for a year, keeping him out of The Invasion storyline. Austin blamed Triple H for costing them the WWF Tag Team Championship, whereas Stephanie blamed Austin for being selfish and not caring for Triple H's well-being. Stephanie would then go on to become co-owner of the ECW alliance during The Invasion storyline, during which Austin turned on the WWF and became the WCW/ECW Alliance's leader. Triple H would make his return on January 7, 2002.
By early 2002, Triple H and Stephanie's marriage was on the rocks, mainly due to Triple H returning as a fan favorite while Stephanie remained a heel. After months of friction, Stephanie tried to fake a pregnancy to hold onto her husband, but Triple H found out with help from Linda McMahon that it was fake, and dumped her in a ceremony when they were about to renew their vows. Stephanie would align herself briefly with Kurt Angle, and later with the Undisputed WWF Champion Chris Jericho and they would continuously torment Triple H in the weeks leading to WrestleMania X8. Yet Triple H managed to overcome the odds and gave both Stephanie and Jericho the Pedigree, winning the Undisputed WWF Championship. The next night on Raw, Triple H defeated Stephanie and Jericho in a triple threat match for the title, with the stipulation that Stephanie would have to leave the WWF if she or Jericho were to lose. Triple H pinned Stephanie for the win and security escorted Stephanie out of the building. Stephanie made her return to the WWE in July 2002 as the new general manager of SmackDown!, with the main purpose of trying to keep Triple H on the SmackDown! brand and prevent him from being lured onto Raw by Eric Bischoff. Triple H and Stephanie had one final encounter at Vengeance, and he decided to jump over to Raw under the encouragement of Shawn Michaels. This also ended their on-screen relationship.
Nine years after the separation of the faction, on the March 30, 2009 edition of Raw, Triple H realigned himself with Vince and Shane to attack Legacy (Randy Orton, Cody Rhodes, and Ted DiBiase), who previously attacked the McMahons, as Orton was feuding with Triple H for his WWE Championship. On the August 24, 2009 edition of Raw, Vince would realign with Triple H, along with original D-Generation X member Shawn Michaels, to once again take on The Legacy.
On the December 17, 2018 edition of Raw, all members of the McMahon family regained control of the Raw and SmackDown brands as part of the massive changes in the aftermath of the TLC: Tables, Ladders & Chairs pay-per-view event, which saw Baron Corbin losing the authoritative role of Raw in a match against Braun Strowman.