2. Worst: Vince McMahon (1999)
With our last bad entry, we talked about the perils of choosing a forty-six-year-old executive as the Royal Rumble winner. The difference between Triple in 2016 and Vince McMahon in 1999, of course being that at one point Triple H was a legitimate main event star in WWE. Vince McMahon meanwhile has never been a full-time wrestler and there is simply no plausible reason why he should ever have won the prestigious Rumble tournament. To be fair, the McMahon win was meant as a stunt to further his rivalry with Steve Austin and his status as the top heel authority figure in WWE. Despite the storyline excuses associated with this choice, VKM should never have come close to a Royal Rumble win, and its moments like this that have served to devalue the Rumble and Rumble winners over the years.
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