According to a key backstage employee, Vince McMahon was sure that The Undertaker would not leave WWE to join WCW. Current WWE Executive Director Bruce Prichard revealed that he and Vince McMahon knew that The Undertaker would not be tempted to join WCW during the Monday Night Wars in the 1990s.
The Undertaker stayed with Vince McMahon's WWE despite many of his peers joining WCW in the 1990s. During one point in the 90s, WWE had financial issues while WCW were paying big bucks to lure top talent from WWE.
While speaking on his Something to Wrestle podcast, Bruce Prichard stated that WCW wouldn't have known how to use The Undertaker. He said that without his Undertaker gimmick, Mark Calaway would have gone back to the Mean Mark gimmick, that wouldn't have done him much favors.
“I was confident that Taker was a WWE lifer. I believe that Vince was confident that Taker was a WWE lifer. It was just timing, and I don’t know that WCW would know what the hell to do with him. You take him out of the gimmick and you go back to Mean Mark, and I truly believe that the Undertaker was such a strong character that you wanted to keep that aura. You wanted to keep that mystery. You wanted to make sure that’s what the audience wanted. I think that’s what everybody wanted," said Bruce Prichard. (H/T 411 Mania)
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Before he joined WWE in 1990, Mark Calaway was a part of WCW, but he was shunned aside by the company. He debuted The Undertaker gimmick, and the rest, as they say, is history.
The stars who quit WWE to join WCW unlike The Undertaker
The Undertaker remained loyal to Vince McMahon and WWE by staying in the company, but there were many who jumped ship to join WCW in the 90s. The likes of Scott Hall, Hulk Hogan, Kevin Nash, Lex Luger, Randy Savage, and Bret Hart were a few of the big names that traded WWE for WCW.
After WCW folded, several of the stars who joined WCW from WWE returned to Vince McMahon's company.