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
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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 fortunately became a fan in time for WrestleMania III and came back as a fan after a long high school hiatus before WM XIV. Monday nights in the Carlson household are reserved for viewing Raw -- for better or worse.
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