Obviously, this is a big alternative history What If — since we know that Punk is a 5 time UFC champ and Lesnar’s run after defeating the Dead Man resulted in the only ******* match Meltzer ever gave (when Roman beat the odds and took the belt at WM32 after Brock’s 720-day reign as WWE World Intercontinental Heavyweight Big Gold Belt Hardcore European Champion.com), but just for funsies:
Do you think that Punk might have stayed in WWE if his bout at WM29 against Undertaker was a "Streak vs Streak" match (putting up his 504-day reign — since Rock/Cena 2: Electric Boogaloo Night Only needed no gimmick to get over, the rumored Punk/Rock match at the Rumble thankfully never happened — against Undertaker’s perfect 20-0 streak going into WM29) that Punk actually won?
I don’t think so, actually. Punk was a deeply unhappy guy and their followup wouldn’t have been any more effective for Punk than what it was for Brock in the short-term. Plus Rock/Cena would have still been the main event in Vince’s eyes, and that was Punk’s whole issue.