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#1 Vince McMahon - 1999
WWE was highly successful during the time Vince McMahon won the Rumble, and hence his victory is not criticised as much as Reigns', Batista's, or Del Rio's. WWE was winning the Monday Night War against WCW, and shortly afterwards, WCW was put out of business.
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However, Vince McMahon winning the Rumble is one of the stupidest decisions made in history. Royal Rumble has a prestige and novelty factor about it, which is lost when non-wrestlers win the whole thing!
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Vince McMahon is probably one of the greatest characters to have graced our televisions. He led WWE to victory in Monday Night Wars. However, his Rumble victory was a terrible decision at the time, and should have never happened in the first place.
Shane McMahon winning the "Best in the World" trophy is similar to his dad's Rumble victory 20 years ago.
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