When Vince McMahon… entered the Royal Rumble
Vince McMahon is easily the most important and polarizing figure in WWE history. For years, he worked behind a microphone as a play-by-play announcer for his own federation, with little to no acknowledgement that he was the owner of the company.
Then came the mid-90’s and the birth of the Attitude Era. Suddenly, Vince was now evolving into his ‘Mr. McMahon’ character and showing his heel tendencies. Before long, he would be in a full-fledged feud with his top star, Stone Cold Steve Austin.
This turn of events began to get more and more physical until it all came down to one thing: Vince McMahon had to get physical himself; he had to face his antagonists in the ring.
This led to Mr. McMahon training profusely for his opportunity at WWE’s 1999 Royal Rumble
— Wrestling from 80s/90s (@Wrestling80s90s) December 28, 2021
This led to some of the funnier bits in WWE history, as the Chairman was shown training, Rocky Balboa-style, in preparation for the big event.
These vignettes may have been designed as comic relief, since no one really took the middle-aged McMahon as a serious threat to The Rattlesnake. As a novice in the ring, he would surely be tossed out as quickly as yesterday’s garbage, right?
However, no one was laughing when they got a closer look at the WWE Chairman’s conditioning. It was clear that this was not Vince McMahon’s first time throwing around some iron. The boss was no stranger to the gym. In fact, he was in better shape than some of his own performers were.
When Vince McMahon finally entered the 1999 Royal Rumble, he was more prepared than many gave him credit for
1/24/99: VINCE MCMAHON WINS THE ROYAL RUMBLE! pic.twitter.com/fuKMTKBJBg
— OVP – Retro Wrestling Podcast (@ovppodcast) January 25, 2021
McMahon would enter the match at number two, but eventually eliminated Austin to capture the Rumble and a shot at the WWE Championship.
He did receive a little help thanks to a distraction from The Rock, but the record still stands, nonetheless: On January 24, 1999, Vince McMahon became your WWE Royal Rumble winner.
He would vacate his title shot the next evening on Monday Night RAW, but the dye was already cast. Mr. McMahon was no longer just a crazy character in the WWE Universe; he was a full-fledged fighter. There was no going back at this point.
This would lead to Austin challenging McMahon to a cage match the following month at In Your House: St. Valentine’s Day Massacre, where the devious owner would again steal a victory through nefarious means.
The battle had now officially become a war, and Vinny Mac wasn’t backing down. He got his first taste of in-ring competition and was determined to go blow-for-blow with any competitor who dared to cross his path.
The days of Vince McMahon as a mild, mannered reporter were gone. He had been replaced by a super villain who would rule WWE with not only his words, but his fists, if necessary.