The biggest “evil authority” storyline in the Attitude Era of WWE concerned Steve Austin’s struggle against Vince McMahon and The Corporation, which famously became the evil mega-stable The Corporate Ministry in 1999. But later that year came a new evil faction in the form of The McMahon-Helmsley Regime. The group was centered around Triple H and Stephanie McMahon as top heels and bosses in the company, and they were backed by members of D-Generation X and a host of other bad guys.

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Let’s take a look at how the saga unfolded, a narrative which involves an in-ring wedding, lots of McMahon family in-fighting, and a love triangle with Kurt Angle.

10 Steph and Test

The origins of the McMahon-Helmsley Regime began in a storyline romance between Stephanie McMahon and Test. Steph’s brother Shane didn’t approve of this relationship, and so he took on Test in a “Love Her Or Leave Her” Greenwich Street Fight at SummerSlam 1999, with the Test/Stephanie relationship on the line.

Test won, and the two were meant to be married in an in-ring ceremony. However, Triple H interrupted the nuptials with a video revealing that he drugged Stephanie McMahon and already married her in Vegas.

9 The Faction Forms

This revelation led to a feud between Triple H and Stephanie’s father Vince McMahon, which came to a head at Armageddon, in a match where Triple H would earn a shot at the WWE Championship if he won, or an annulment of his marriage if he lost.

Trips won the match, and Stephanie would then reveal she was in on the marriage, having done it to get back at Vince for trying to marry her off to The Undertaker, thus tying up a weird plot hole in the Higher Power storyline.

8 Consolidating Power

The McMahon-Helmsley Era was officially announced on screen on Raw, following the Armageddon match, and from there the group started gaining power. Triple H would beat Big Show for the WWE Championship, his buddies The New Age Outlaws would be successful in the tag division, and Stephanie McMahon would later become Women’s Champion.

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As the rest of the McMahon family -- father Vince, mother Linda, and brother Shane -- were off television, Triple H and Stephanie became the top heel authorities in WWE, with their titles ensuring their place of power.

7 The Feud With Mankind

One of Triple H’s first big feuds in this era was against Mick Foley, a.k.a. Mankind. The Regime had The Rock and Mankind fight for their jobs, which the latter lost, but The Rock and the rest of the babyface roster rallied for Mankind to get his job back.

This led to a famously brutal street fight between Mankind -- now reverted to his Cactus Jack persona -- and Triple H at Royal Rumble 2000. Triple H would win that match, followed by a Hell in a Cell match at No Way Out with Cactus’ career on the line.

6 WrestleMania 2000

In the weeks leading up to WrestleMania 2000, the rest of the McMahon family resurfaced, with each one backing a different wrestler. This resulted in the “McMahon in every corner” main event of ‘Mania; a four-way between The Rock, Big Show, Triple H, and Mick Foley, who had immediately been brought out of retirement.

Eventually Vince and Shane would turn their backs on their chosen wrestlers to align with Triple H and Stephanie, taking things to a whole new level.

5 Power Trip

Like any good evil authority storyline, the stable exists to keep one top champ in power, and so the McMahon-Helmsley Regime worked to keep the WWE Championship on Triple H.

This included incidents like Chris Jericho defeating Triple H for the title, only for the Regime to strongarm referee Earl Hebner into reversing the decision and firing him in the process. Triple H would ultimately beat Jericho in a Last Man Standing match at Fully Loaded 2000, but the firing of Hebner would come back to bite them.

4 Trips Loses To The Rock

Triple H’s biggest feud of this run was against The Rock. Their big title match at Backlash had Shane McMahon as the guest referee, all but guaranteeing a Triple H win. But The Rock would take out Shane for his biased actions during the match, and Steve Austin would even the odds by hitting every Triple H loyalist with a chair.

That’s when Linda McMahon returned to reinstate Earl Hebner as referee, who was able to count the final pin in The Rock’s favor.

3 The Rock Loses To Trips

The Rock’s initial title run in this storyline would last about three weeks, ending with an Iron Man match against Triple H at Judgment Day. Over the course of the hour-long bout, the two would tie it up 5 to 5 amidst interference from Triple H’s friends, but The Undertaker’s interference on The Rock’s behalf would draw a DQ, therefore giving the final winning point to Triple H.

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This would lead to a six-man tag match at King of the Ring with Rock, Undertaker, and Kane against Triple H, Vince McMahon, and Shane McMahon, with the stipulation that a pinfall on Triple H’s team awards the title to the winner. The heels obviously thought the good guys wouldn’t be able to co-exist, but The Rock ended up pinning Vince McMahon to become WWE Champion again.

2 The Love Triangle

As the Regime gradually wound down over the course of 2000, Kurt Angle would align with them during Triple H’s feud with The Rock, but the partnership would ultimately be undone thanks to a blossoming love triangle among Angle, Stephanie, and Triple H.

The Rock would beat both Angle and Triple H in a Triple Threat at SummerSlam 2000 and Triple H would beat Angle in a No DQ bout at Unforgiven. But Angle would capture the title and retain against Triple H at the 2001 Royal Rumble pay-per-view.

1 The End of the Regime

Ultimately, the McMahon Helmsley Regime would slowly fizzle out, gradually declining as members of DX disappeared from television and members of the group moved on to other concerns.

WrestleMania X-Seven would end with the Steve Austin heel turn and alliance with Triple H and the McMahons as The Power Trip, but an injury would put Triple H out of action for a year. The Invasion storyline would have Vince and his kids on different sides of the conflict. In 2002, Triple H would return as a babyface and kayfabe divorce Stephanie onscreen.

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