Ranking All 30 WWE Royal Rumble Winners

22. Randy Orton – 2009

steve austin 2001 royal rumble
WWE.com

WrestleMania title shot: Lost to Triple H at WrestleMania XV

Wrap your head around this one: Randy Orton won the 2009 Royal Rumble by last eliminating Triple H. He then lost his title match at WrestleMania to… Triple H. Orton would then go on win the title a month later from Hunter.

On top of this ridiculous booking was the equally ridiculous storyline of Orton assaulting all the members of the McMahon family, which finally brought Triple H and Stephanie’s real-life marriage into WWE canon. This also includes the unintentionally comical Triple H home invasion that has become legendary for all the wrong reasons.

Orton-Triple H would have been a decent grudge match on its own at Mania, but WWE decided to have Hunter win the title at Elimination Chamber, bringing the WWE Championship into the mix. Then that match went on in the main event and was completely overshadowed by the legendary (for all the right reasons) Undertaker/Shawn Michaels match.

This is the very definition of failure.

Contributor
Contributor

Scott is a former journalist and longtime wrestling fan who was smart enough to abandon WCW during the Monday Night Wars the same time as the Radicalz. He fondly remembers watching WrestleMania III, IV, V and VI and Saturday Night's Main Event, came back to wrestling during the Attitude Era, and has been a consumer of sports entertainment since then. He's written for WhatCulture for more than a decade, establishing the Ups and Downs articles for WWE Raw and WWE PPVs/PLEs and composing pieces on a variety of topics.