Big Show was one of the top main event draws in WCW during the height of the Monday Night Wars, winning two World Heavyweight Championships and acting as one of the very few foes against the New World Order.
But not long after Big Show (who wrestled as 'The Giant' in WCW) joined the nWo, he grew tired of being underused and jumped on the opportunity to sign a 10-year contract with WWE in 1999.
It turned out to be a massive gain for the WWE, and a brutal loss of talent for WCW. Nonetheless, former WCW boss Eric Bischoff explained on the 83 Weeks podcast (h/t WrestlingInc.com), why he has no regrets in encouraging Big Show to take WWE's lucrative offer.
"I didn't mind when Paul Wight (Big Show) came to me and said WWE offered him $1 million a year for ten years. I was like dude, you need to take that. You need to go now, lemme give you a ride to the airport.
That was then, Paul's obviously matured. Paul was very young at the time and was going through a lot of other stuff. Paul's clearly gone on to be somebody you know, noteworthy in the industry. But at that time, man, he just wasn't putting a lot into it."
Big Show debuted for WWE at the St. Valentine's Day Massacre: In Your House pay-per-view on Feb. 14, 1999, breaking through the canvas of the ring and attacking 'Stone Cold' Steve Austin in his Steel Cage match against Vince McMahon. From there, Big Show aligned himself with The Corporation faction and embarked on a run that'll surely put him in the WWE Hall of Fame someday.
The Monday Night Wars stemmed from WCW and WWE taking away top talents from the other. It began with Bischoff signing away the three legends that would form the nWo, but Vince and co. countered by stealing the likes of Big Show, Chris Jericho, Eddie Guerrero and Rey Mysterio.
Bischoff's explanation for letting Big Show go makes plenty of sense, and it's hard to be critical of him for making that difficult decision. He simply didn't value Big Show enough to be a main eventer, but Vince McMahon was willing to jump on and find his next great big man.
Had Big Show never taken that contract from WWE, there's no telling just how different the history of professional wrestling could have been.