5 times WWE Chairman Vince McMahon has apologized 

#1: CM Punk

CM Punk

CM Punk had faced an uphill battle for stardom throughout his tenure in the WWE. From being dismissed by Triple H in 2005 during a tryout match, to his lackluster first run as World Heavyweight Champion in 2008 which ended during a match Punk was not even a part of. This all changed during a 2011 edition of Monday Night Raw when Punk cut his famous Pipe Bomb promo.

Punk voiced every grievance he had toward the WWE machine and his anger toward The Rock being in the main event of WrestleMania instead of him. The promo would kick off the fabled Summer of Punk that saw the Superstar capture the WWE Championship from John Cena at Money in the Bank before leaving the company with the title.

However, the truth behind the promo remained true for Punk as this storyline wrapped up and through a combination of fatigue, injury, concerns regarding the health & safety practice of WWE doctors, and creative frustration Punk walked out of the WWE following the 2014 Royal Rumble. The internet was set ablaze and chants of "CM Punk" filled arenas all across America.

Punk would be officially released by the WWE shortly after that year’s WrestleMania. Punk would then appear on Colt Cabana’s podcast to provide fans with an explanation as to why he had walked out on the WWE. Punk alleged he had been encouraged to work while concussed, given a Z-Pak in response to a serious infection, and that when he finally was released by the WWE it was via fax on his wedding day.

Following on from this in a move few would have predicted Vince McMahon would appear on the Stone Cold Podcast on the WWE Network and would discuss the firing of CM Punk going as far as to apologize to the former champion for him being fired on what should have been a joyous occasion, though he claimed it was merely a coincidence.