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4. Exiling Randy Orton From Evolution, 2004
The Cerebral Assassin aspect of Triple H’s character has seen him portray the mastermind behind a number of schemes. That included drugging and marrying Stephanie McMahon (in kayfabe), plotting Steve Austin getting run over in a parking lot, attacking Shawn Michaels upon his comeback to the ring, and facilitating Seth Rollins’s heel turn as he split from The Shield.
For all of these big moments, few are memorable or downright evil as his betrayal of young Randy Orton as Helmsley kicked him out of Evolution. The moment was particularly sharp because, while fans may have expected this to ultimately be how their partnership wound up, hardly anyone predicted as abruptly as it happened. Giving Orton the thumbs down was a brilliant, electric moment before Triple H had Batista drop The Legend Killer, en route to Helmsley leading a brutal beat down. While Orton’s face run may not have panned out as WWE hoped, this was nonetheless one of the most iconic moments of the era, and for Orton and Triple H’s respective careers.
