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Kurt Angle didn't have complete creative control and his initial feud with Joe was a disappointment. They made numerous bad decisions during that early period so any Angle fans who followed him didn't stay long.
CM Punk surpassed Kurt Angle in popularity. And again, I don't think the size of the audience would matter that much to Punk if he really just wants to fully express himself. You're assuming he would go to TNA to make them competitive with the WWE. That simply isn't going to happen. What could happen is that Punk goes to TNA and just has tremendous matches, promos and feuds with people allowed to let it all hang out.
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