What if Triple H had signed with WCW in 1999?

In 1999, Triple H’s WWE contract was up. Bruce Prichard commented on this recently, noting that WWE wasn’t really fearing losing stars to WCW at that stage because the tide of the Monday Night War had clearly turned. Nonetheless, WWE did get into the habit of locking down stars for longer-term contracts at that stage, including signing The Game for five more years.

There’s little indication that Triple H was going to jump ship. He had signed with WWE when momentum was arguably headed in the opposite direction, with WCW on the upswing, and when Vince McMahon couldn’t offer him as much money, because he felt it was the best place for him to grow as a performer. Just the same, with Helmsley’s friend from The Kliq, Kevin Nash, increasingly a power broker, might the Cerebral Assassin have been tempted?

This article takes a look at what might have been had Triple H signed with WCW in 1999.

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#5 Triple H in the nWo 2000

The nWo 2000 almost certainly would have included Triple H, possibly in place of Bret Hart.

The original New World Order angle was largely played out by 1999. Hollywood Hogan had been through his major programs with Roddy Piper and Sting, and the red and black Wolfpac had splintered and then reunited with black and white.

However, WCW understandably went back to the well on its most profitable angle in 2000. Bret Hart was a key player—a necessary addition to sell the group as fresh-faced but still elite, but also an awkward fit because the heel super group anchored by members of the Kliq didn’t really fit his personality.

Triple H could have ably filled Hart’s spot in this new take on an old group. What he lacked in Hart’s world title credentials in 1999, he could have made up for in both still being in his legitimate prime physically, and the buzz of recently defecting from WWE. Moreover, working alongside Kevin Nash and Scott Hall, the group might have had a more natural chemistry on top and a better chance at succeeding.

#4 Shane McMahon prospers

Had Triple H not married Stephanie McMahon, Shane's stake in WWE may be far greater.

Triple H and Stephanie McMahon are WWE’s ultimate power couple, positioned to fully take over WWE whenever Vince McMahon decides to hand over the reins, or, at least equally likely, passes on. Based on Helmsley’s work with NXT, he seems well suited to leading creative and talent management. The Game wouldn’t be positioned to take on a role like this, however, had he not married into the McMahon family.

The timeline and details are a bit fuzzy about when he and Stephanie actually became a couple, but the narrative they’ve generally put forth was that they got together in a case of life imitating art after they came together on screen for WWE storylines in late 1999. There’s little reason to believe Stephanie would have gotten into a serious relationship with him had he jumped to the competition, which at the minimum would have made it less practical for them to date.

Conceivably, they might have wound up linked anyway after WWE acquired WCW, but that at minimum would have shifted the timeline and given Vince some pause about his son in law. Shane McMahon is generally perceived as the loser in The Authority’s rise to power, as he went from the presumptive heir to the WWE empire to, at best a future third in command. Without Triple H in WWE, Shane may well be on his way to running WWE or at least doing so as a more equal partner to his sister.

#3 Bret Hart is miserable

Bret Hart would not have been happy to have seen another Kliq member show up in WCW.

Bret Hart has made no bones about not getting along with The Kliq in WWE. A lot of that roots back to Shawn Michaels and the professional jealousies between the two, all of which culminated in the Montreal Screwjob. Cooler heads have prevailed in the respective performer. But, back in the year 1999, the wounds were still very fresh.

In the performers’ advanced age, Hart and Michaels have made up. There are still hints of tension between Helmsley and Hart—including the Hitman suggesting The Game was never an all time great—but we can nonetheless assume they co-exist peaceably when they have to. Had Triple H followed Hart to WCW in 1999, though, we can only assume that the Cerebral Assassin would have made life even more miserable for the Excellence of Execution, even if Helmsley hadn’t consciously tried all that hard to.

#2 No world title reign for Booker T

With another young main event incumbent and skilled politician in the mix, it's uncertain Booker T would have gotten his shot on top in WCW.

Booker T was one of the very few and arguably the last legitimate main event level star that WCW built from the ground up. Moving from the more athletic half of a solid tag team to a mid-carder with a lot of potential, Booker finally got pushed all the way to the top in WCW’s dying days. Much of the marquee talent was on the shelf, grappling with contract issues, or increasingly not performing like top guys. Booker got the opportunity so many fresh talents seemed to have been waiting on for years.

Had Triple H been in the mix in WCW, it’s hard to imagine he wouldn’t have won the world title. Not only was he a can’t miss talent, but his skill with playing politics and his friendship with Kevin Nash—who was in and out of the booker role—meant the Cerebral Assassin likely could have gotten on top and stayed on top for some time. Top stars of WCW’s final years like Scott Steiner, Jeff Jarrett, and particularly Booker T may then have been out of luck in ever getting their turn on top had Triple H signed.

#1 A far better version of Triple H vs. Scott Steiner

Triple H vs. Scott Steiner could have been far better just a few years earlier.

In 2003, WWE fans saw one of the worst main event level feuds of the era when WCW headliner Scott Steiner arrived to challenge Triple H for the World Heavyweight Championship. Big Poppa Pump was miscast in a face role, the build felt oddly old school for its focus on arm wrestling contests and posedowns, and Steiner immediately proved himself as out of shape for a main event level match when the two squared off at the Royal Rumble PPV.

On paper, the program should have worked in setting up a first-time match between two big-name stars with excellent promo skills and the ability to deliver in the ring. The biggest problem of all? WWE was too late. Steiner was past his prime and out of his element in 2003. While Helmsley was talented, he certainly wasn’t his most buzzworthy in this era. Pitch this match three years earlier in a WCW ring and it may well have been something special.