#4 Eric Bischoff's firing
By the end of 2005, the WWE Universe had gotten tired of Raw GM Eric Bischoff consistently trying to dethrone John Cena from the top spot, by using any means necessary. It seemed like Vince McMahon had sensed that the fans were done with this modern-day incarnation of Stone Cold vs Vince McMahon, and thus a trial was set up for Bischoff on an episode of Raw.
Also read: 5 things current heels should learn from Vince McMahon
McMahon took the role of a judge, and the trial continued throughout the episode. In the end, Vince confronted Bischoff in the ring but was soon interrupted by John Cena. Soon after, Vince delivered the judgment, firing Bischoff in the process. Cena hit an FU on Bischoff and Vince dumped him in the back of a garbage truck, to a loud ovation.
#3 The Undertaker kidnaps Stephanie
The year 1999 is regarded by many as the peak of the Attitude Era. Possibly the biggest storyline that year was Stephanie McMahon coming in as an on-screen character and The Undertaker kidnapping her in a heelish act. This prompted Vince to seek assistance from Stone Cold Steve Austin, his arch-enemy. This was the first time in a long while that Vince McMahon was portrayed as a babyface in a storyline, garnering him tons of fan support and sympathy.
The end to the angle saw Vince McMahon revealing that he orchestrated the entire scheme, and came out as the higher power, immediately turning heel. Things didn't end well for him though, as an irate Linda McMahon gave Stone Cold the position of WWE's CEO.