#3 Vince McMahon and CM Punk
Based on various interviews over the last few years, it seems that Vince McMahon had many brutally honest conversations with CM Punk in WWE.
One of the most extreme examples of this came in 2013 when Punk told Sam Roberts on the weekend of WrestleMania 29 that Vince McMahon once said he was more difficult to deal with “than Shawn Michaels when he was on drugs”.
Punk ended up leaving WWE in January 2014 when he walked out on the company after a meeting backstage with Vince McMahon and Triple H.
The former WWE Champion called out both men for numerous reasons, including Vince McMahon for making false promises and Triple H for not allowing him to win when they fought at Night of Champions in 2011.
Punk explained during his infamous appearance on Colt Cabana’s Art of Wrestling podcast that he received confirmation of his WWE firing on his wedding day – something that Vince McMahon later apologized for.
Although Punk began discussing the modern-day WWE product on FOX show WWE Backstage in 2019, he has still not made a televised WWE appearance since 2014.
The Wrestling Observer’s Dave Meltzer reported in 2020 that Vince McMahon has even labelled Punk as “the one man he can’t do business with”.