Vince McMahon‘s involvement in the 1999 Royal Rumble is considered one of WWE’s most infamous moments. At that time, McMahon was embroiled in his iconic rivalry with Stone Cold Steve Austin and eliminated The Rattlesnake to win the 30-man over-the-top-rope Battle Royal.

During a recent edition of What Were They Thinking? on Backstage Pass, Gerald Brisco revealed the real reason why Vince McMahon won the 1999 Royal Rumble match, noting it was meant to expand on the evil boss character, which had previously been seen as an executive by the fans.

“Well, I’ll tell you what we’re what we’re thinking there. It was just to elevate Vince McMahon’s character a little bit to kind of prove that he belonged in the ring. (Vince) had the promos and the mannerisms to him. But he was never, you know, what you call a five-star type of worker.” [From 08:11 onwards]

The WWE Hall of Famer said the feedback they got out of the win wasn’t entirely positive, as many wrestlers backstage questioned the outcome of the infamous match.

“They got a lot of feedback and not all positive feedback too. Even some of the guys were why Vince was winning this thing, but they didn’t understand where we were going with Vince McMahon’s character at the time. It was just like anybody that goes over in that Rumble…it’s something that elevates your character and elevates your position in the company. So we wanted to prove to the fans that this was the way to do it.” [From 08:42 onwards]

McMahon would relinquish his opportunity to face The Rock for the world title before Steve Austin re-entered the title picture by defeating his boss inside a steel cage in February 1999.

The former chairman of the board would (inadvertently) capture the WWE Championship months later.

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