28. Vince McMahon 1999
WrestleMania title shot: Never cashed in; Went to runner-up Stone Cold Steve Austin Without a doubt, this is the worst Royal Rumble winner on record, as Steve Austin and Vince McMahon entered at #1 and #2 respectively and proceeded to spend the vast majority of the match outside the ring. The ending pretty much mirrors how many Raw matches end today: someone (in this case, the Rock) comes out and distracts someone (Austin) and the opponent (Vince) picks up the victory (eliminating Austin, in this case). McMahon refused to face Rock, so WWF Commissioner Shawn Michaels named runner-up Austin the #1 contender. McMahon would face Austin in a steel cage match for the title shot at St. Valentines Day Massacre, where Big Show would debut and inadvertently help Austin win. https://www.youtube.com/watch?v=E_fu5C2804w Austin went on to win the WWF Championship at WrestleMania XV, but what should have been a straight road to WrestleMania instead was full of unnecessary hairpin turns.
Scott Carlson
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.
See more from
Scott