4. CM Punk
Out of all the missed opportunities related to his streak, perhaps the biggest one was the failure to put over CM Punk at WrestleMania 29 in 2013. It could have changed the course of history dramatically, giving Punk the reassurance that he was a valued employee. It is hard to imagine he would have left a year later if he'd had that investment put into his character. WWE could have even sold the big rematch a year later for Mania 30, Punk vs Taker 2 for the deadman's revenge. It was what Punk needed, the title of 'streak conqueror' to make up for his removal from the WWE Title scene. He was a huge star, but WWE weren't really treating him like a huge star. As perhaps the most deserving person to ever go up against Taker's streak, it was a missed opportunity to not put him over.