WWE's Biggest Booking DISASTER Every Year (1986-2026)

19. CM Punk’s First World Title Run (2008)

CM Punk World Heavyweight Champion
WWE.com

2026's Money In The Bank ladder match build saw CM Punk talk up his chances of hauling down the briefcase for a historic third time. Previously, he'd won it in 2008 and 2009. Yes, yes that does feel like several lifetimes ago.

Punk cashed in on Edge after some Batista involvement on the 30 June '08 Raw to win the old World Heavyweight Title for the first time. That's when the fun stopped. WWE positioned Punker as someone totally out of his depth in amongst the big boys in the main event scene.

Batista went after him first, and commentary stated that CM beating 'The Animal' was against all odds. Then, as a follow up, JBL ridiculed the straight edge star for even thinking he could match up against WWE headliners. Punk was a fraud as champ - that's the message fans were beaten over the head with on every show.

By Unforgiven in September, Punk was removed from a 'Scramble Match' later that night, replaced by Chris Jericho and demoted back down to the mid card. Pushing him skyward via MITB and by winning the World Title should've added a fresh player to the main event deck, but no.

Management got cold feet, or somebody got in Vince's ear about Punk 'not being ready' for that spot. Post-Unforgiven, he was put in a tag-team with Kofi Kingston (another guy who'd suffer from an abandoned WWE push).

The 'Scramble' decision made JBL's words ring true. Punk didn't belong at the top in the eyes of those calling plays.

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Lifelong wrestling, video game, music and sports obsessive who has been writing about his passions since childhood. Jamie started writing for WhatCulture in 2013, and has contributed thousands of articles and YouTube videos since then. He cut his teeth penning published pieces for top UK and European wrestling read Fighting Spirit Magazine (FSM), and also has extensive experience working within the wrestling biz as a manager and commentator for promotions like ICW on WWE Network and WCPW/Defiant since 2010. Further, Jamie also hosted the old Ministry Of Slam podcast, and has interviewed everyone from Steve Austin and Shawn Michaels to Bret Hart and Trish Stratus.