#5 CM Punk

Although CM Punk was the hottest wrestler in WWE (and the world) for a while, and even though he was a two-time WWE Champion and two-time World Champion, WWE still missed some big opportunities with him pretty early on.
While WWE had often chosen the right Rumble winner during the 2000s, I think a big misstep for them was the only 40 man Royal Rumble match in 2011, with Alberto Del Rio winning.
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Now Del Rio was a fine talent, but his winning of the match didn't really make him the star WWE wanted to. He did achieve this level later on that same year, but not here.
CM Punk at this time was the new leader of The Nexus, WWE's hottest angle of 2010. Punk as leader would end up doing more damage to the dwindling group.
But at this time, it was still salvageable and a great way to put it over would have been for CM Punk to have come out on top, especially since the group were feuding with company face John Cena at the time. Thankfully, Punk salvaged his own career later that year.