5 times WWE Chairman Vince McMahon has apologized 

#2: Bret Hart

Bret Hart

It has been well-documented that the relationship between WWE Hall of Famer Bret Hart and Vince McMahon has been strained to say the very least. Tensions had been high at various points in the mid-’90s due to creative differences and the continued presence of Shawn Michaels in the main event title scene.

Tensions boiled over at the 1997 Survivor Series in the infamous Montreal Screw Job. During a WWE title match between The Hitman and HBK McMahon ordered referee Earl Hebner to call for the bell awarding the submission victory to Michaels, though Hart had not tapped out. Despite having all the makeup of a storyline angle this was a very real moment, one that would allow fans a peek behind the curtain of WWE backstage politics and would go on to help to usher in the Attitude Era.

After the show went off the air, The Hitman was understandably upset at what had happened and the locker room became tense as stars chose sides. One man not often brought up when speaking about this incident is The Undertaker who recently shed new light on what transpired after the PPV feed ended. In an interview with ESPN, "The Deadman" discussed his disbelief with what he had just seen and revealed that he had told Vince McMahon to go and confront Bret and say sorry for what had happened.