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He's never had any athletic gifts, but Paul Heyman liked him because he was a good shit-talker, so he plucked him out of the indies and into WWECW. He was a decent enough pair of hands that he could pull off a good-to-great match when paired with the right opponent.
He had a pretty well-regarded feud with Jeff Hardy, but other than that and some Money In the Bank cash-ins he was pretty unremarkable at WWE. That said, he was terminally online, maintaining a LiveJournal well beyond the point where any sane person should, and that combined with his 'legendary' series with fellow indie darling Samoa Joe, Punk kind of became the face of the Internet Wrestling Community in the form that existed in the late 00s and early 10s. Oh, and also combine that with the fact that he's not just a Chicago guy, he makes that a defining part of his personality, so the smarky and loud Chicago audiences always loved him.
These were the years of Super Cena dominating the company, and when he was booked in a feud with Cena towards the end of his contract, Vince gave him the full authority to drop the 'pipebomb' promo. A promo that is 100% a work, but it does incorporate real-life grievances he had, and had enough smarky internet references that it genuinely convinced a lot of people that he was shooting.
The strength of that promo (and the legendary 2011 MITB Main Event, in Chicago) is what kept him in the world title scene for the next couple of years. And the fact that he was world champion for a long ass time, but was barely ever main eventing shows just fueled his reputation as an underdog who deserved to be treated better.
When he finally quit the company in 2014, he released a podcast with Colt Cabana that unironically might be the most impactful piece of wrestling media since Survivor Series 97, where he got to list off all of his grievances with the company. It cemented him as the eternal good guy who was held back by the machine of WWE.
