CM Punk
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While some guys on this list maintained a generally positive relationship with WWE brass, that wasn’t the case with CM Punk. Some of the time he spent in the WWE was downright contentious, and publicly so at times. Further, he didn’t have the prototypical look Vince McMahon typically likes.
Yet, CM Punk was still one of the best performers in the world, and for that reason, he was pushed to a major title reign that lasted for more than 400 days – one of the longest such runs in decades.
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Further, he remains the only two-time winner of the Money in the Bank Ladder Match.
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Edited by Staff Editor