What if Triple H had signed with WCW in 1999?

#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.