#2 Sting
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The Icon Sting was to WCW what The Undertaker is to WWE. He was the WCW captain to go down with the WCW ship.
Sting had claimed several times over the years that he didn't want to go to WWE due to a fear of how they would book him, citing Booker T and Diamond Dallas Page's poor runs as an influence.
However, in early 2002 shortly after WWE announced the signings of Hulk Hogan, Scott Hall and Kevin Nash, it was leaked that WWE had been negotiating with a few other former top WCW stars, one of which being Sting.
Apparently, at one point WWE considered Sting coming in as a lock and planned a match between him and Kurt Angle for WrestleMania 18, however Sting backed down, returning to his previous concerns over how they would book him, as well as not being too thrilled with WWE's particular TV-14 style content at the time.
When many thought he was retired for good, Sting surprised everyone when he returned to wrestling in early 2006, and not to WWE, but TNA Wrestling. Sting would go onto have a seven-year run with the company, where he held the NWA World Championship and was a 4 time TNA World Champion.
Sting finally signed a deal with WWE in November 2014 and debuted at the Survivor Series. He wrestled four matches for WWE before being forced to retire after a neck injury in 2015. Today, he is a member of both the WWE and TNA Hall of Fame.