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#1 Bret "The Hitman" Hart (regretted joining WCW)
Bret Hart had an incredible career in WWE and was a part of the main event picture for years on end. He was essentially the face of the company in the mid-90s, and had one of the greatest rivalries in WWE history with Shawn Michaels. Unfortunately, he wasn't a fan of Shawn in a real-life. Hart bagged a contract with WCW in 1997 and made it clear to Vince McMahon that he didn't want to drop the WWE title to Michaels at Survivor Series.
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This led to Vince double-crossing Hart in Montreal. In an appearance on WWE Backstage, Hart stated that he regretted his decision to join WCW. When Booker T asked if he would like to change things if he got another chance. here is what Hart had to say in response:
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"I think I figure out a way to stay in WWE. Knowing what I know about WCW, I'm sorry I ever went there."
Hart was a 2-time WCW World Champion and won several other titles, but wasn't used by the company to the best of his abilities. Hart also suffered a career-ending injury at the hands of Goldberg in WCW.
