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#2 CM Punk
CM Punk was one of the longest reigning WWE Champion in the modern era. He was a two-time Money in the Bank winner, former tag-team champion and was one of WWE's top stars in the early 2010s before his departure in 2014. It's a huge disappointment that a star of his calibre hasn't won a Royal Rumble match.
Punk competed in multiple Rumble matches and had a great record in the Rumble match, having eliminated 7 men in the 2011 Royal Rumble match. His very last appearance in WWE was in the 2014 Royal Rumble match, where he lasted about an hour and entered the final four before being eliminated by Kane. Punk walked out of WWE the next night and hasn't been seen in a WWE arena ever since.
It's highly likely that Punk would've won the Rumble match in the coming years had he stayed with the WWE. Now that Punk is done with the WWE, it's unlikely that he'll ever win a Rumble match.
