4. Trish Stratus: WrestleMania 20
Next on our list, we have Trish Stratus. Her heel turn took place not in a match where she was competing, but during a bout involving the two men she was entangled with in a love triangle storyline: Chris Jericho and Christian.
The initial turn happened at the end of the match, when Stratus appeared to try to help Jericho, but instead “accidentally” elbowed him. This maneuver gave Christian the opening he needed to win the match. In the aftermath, Trish cemented her betrayal by repeatedly slapping Jericho before leaving the ring with Christian. The final visual was of Christian and Trish kissing on the ramp while a devastated Jericho looked on from the ring.
This heel turn was the perfect dramatic moment, especially during that time. It provided an unforgettable end to a masterfully crafted five-month love triangle storyline that the crowd was heavily invested in, making it one of the most iconic, heart-wrenching moments in WrestleMania history. This move helped propel Stratus, a long-time babyface, toward the highlight of her career: her dominant 448-day run as Women’s Champion.
3. Triple H: WrestleMania 15
Our next entry features a heel turn involving Triple H. This didn’t happen in a match he was competing in, but rather one featuring his fellow D-Generation X member, X-Pac, who was facing The Corporation’s Shane McMahon for the European Championship. There was an interesting element for this heel turn, one that separates it from the rest on this list.
Earlier in the night, Chyna betrayed The Corporation, seemingly reuniting with Triple H and DX. But later on, when Triple H and Chyna appeared during X-Pac’s match to assist him, Triple H delivered his signature Pedigree. This move helped Shane win the match and marked Triple H’s official defection to The Corporation.
This turn earns its spot on the list because it was the exact moment that paved the way for Triple H to become a main-event player and the multi-time World Champion fans grew to love. Before this night, Triple H was the highly popular babyface leader of DX. Afterward, he transformed into the corporate, cutthroat “Game” persona that would dominate the WWE landscape for the next ten years.
