#2 WWE to WCW - Macho Man Randy Savage
To this day, there are still arguments over why, after so long and so much success, the Macho Man walked out on WWE in 1994. Eric Bischoff himself has gone on record regarding the Macho Man's exit, stating that the actual reason was that the larger than life Superstar simply wanted to prove himself outside of the confines of WWE. Regardless of the reason behind it, it was still jarring for Vince to announce live on the air that Savage had left and robbed WWE of one of its best performers and icons.
Savage would eventually join WCW, and while he did go on to find moderate success there it never even came close to living up to his WWE tenure. It was obvious that Vince McMahon never got over his abrupt exit as Savage basically became persona non grata on various DVDs and such until his untimely death.
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At the time of his death, Savage had started to mend fences with WWE that had previously been torn apart by his betrayal, but unfortunately we never got to see him grace WWE TV one last time.