#2 The Radicalz jump to WWE (January 3, 2000)
In the mid-1990s, the major players in wrestling were abandoning WWE en masse. Hulk Hogan, Macho Man Randy Savage, Lex Luger, Roddy Piper, Kevin Nash, Scott Hall, Bret Hart and others left WWE for WCW. However, after WCW entered what turned out to be a terminal decline in spring 1999, wrestlers began to move the other way. The Giant (Big Show) jumped ship to WWE in February 1999 and Chris Jericho followed in August 1999.
But the final nail in the coffin of marketable mid-card talent who could potentially be main event players departing WCW, occurred on January 31, 2000, when former WCW world champion Chris Benoit and mid-card stars Eddie Guerrero, Dean Malenko and Perry Saturn all switched sides to WWE on the exact same night. Malenko had reigned as Cruiserweight Champion (four times), United States and Tag Team Champion. Guerrero had also reigned as the Cruiserweight Champion (twice) and held the United States strap, while Saturn held the Television Title and Tag Team belts (twice).
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Benoit, who was signed for a much larger guaranteed downside, had been on top of the WCW World Title, held the television strap (three times), United States Title (twice) and Tag Team Championship (twice). These were four names whom WCW could ill afford to lose and Benoit and Guerrero went on to become much bigger names under the WWE umbrella; most famously ending Wrestlemania XX as the World Heavyweight and WWE Heavyweight Champions, respectively. In one fell swoop, WCW had lost almost all of its mid-card roster and most worryingly of all, the Radicalz departure exacerbated a trend of WCW stars joining WWE.