After buying the WWWf from his father McMahon's male role was commentating and supporting the faces. WWF Champion Bret Hart was set to be challenged by Shawn Michaels at survivor series 1997. This was bad for McMahon as Hart was ready to leave for his competition WCW and did not want to drop the belt to Michaels.
When Michaels had locked Hart in the sharpshooter McMahon ordered the official to ring the bell screwing Hart out of the title and began his first heel run. McMahon would claim Hart only had himself to blame furthering fan's outrage against him.
McMahon was upset when his archenemy Stone Cold Steve Austin won the title from Shawn Michaels at WrestleMania 14. he forced Austin into fighting him with one arm tied behind his back. However before the match could be started McMahon's new ally Dude Love came out to attack Austin. Following this McMahon named Dude love the number one contender for Austin's championship. Dude love won their encounter at unforgiven but by disqualification meaning Austin kept the belt.
Dude was granted a re match at over the edge With McMahon appointing himself as the guest referee however Undertaker arrived to ensure the match was called fairly. When Dude accidentally hit McMahon with a steel chair Austin won the match and retained the belt. The following night on raw McMahon dubbed Dude an embarrassment to the company as well as to his own family and fired him as punishment for his failure. McMahon was determined to end Austin's reign and tried to do so by employing the services of the Undertaker and his brother Kane making Austin defend his belt in a triple threat match against the two brothers.
They both pinned Austin which left the company without a champion. McMahon then pitted Undertaker against Kane to decide the champion and Made Austin the guest referee stipulating that he would be fired if he did not raise the hand of a new champion. Austin refuse to conform to McMahon's demands as he attacked both men declaring himself champion. McMahon then organized a tournament which ended at the 1998 survivor series. He ensured Mankind made it to the final as Mankind had visited him in hospital after Undertaker and Kane assaulted him.at the finals, however McMahon screwed Mankind out of the belt and assisted the rock in becoming the new champion.
In the buildup to the 1999 royal rumble McMahon stacked the odds against Austin by offering a reward for whoever eliminated him and made him the first entry but Commissioner Michaels used this to make things difficult for McMahon by making him the second entry. McMahon surprisingly Won the rumble due the interference of Rock along with other members of McMahon's faction, the corporation. After McMahon forfeited the right to challenge Rock for his championship at WrestleMania 15 Michaels revealed that the rules in the wwe rulebook stated that if the rumble winner was unwilling/unable to participate in the main event of WrestleMania the runner-up took his place which made Austin the next challenger for the rock's belt.
McMahon and Austin faced off at St Valentine's day massacre in a steel cage match in order to decide the number 1 contender. Big Show debuted and accidentally threw Austin out of the cage which meant he won. At WrestleMania 15 McMahon tried to interfere but Austin defeated Rock anyway.
McMahon and the corporation then became embroiled in a conflict with Undertaker's ministry of darkness who kidnapped his daughter Stephanie. Despite his hatred for McMahon Austin was disgusted by this and saved Stephanie from Undertaker. McMahon revealed he had orchestrated the whole thing including his daughter's kidnapping as a way to get under Austin's skin.
Stephanie and Vince's enraged wife Linda exacted revenge by giving their shares of the company to Austin making him own 50 0/0 of the wwe, Austin defended his share of the company in a handicap ladder match against Vince and his son Shane which the McMahons surprisingly won. After Austin defeated Undertaker, McMahon was banned from WWF tv, he resurfaced as a face to fight Triple H and won the wwe championship from him because of Austin's interference (he voluntarily vacated the title and gave Austin the title shot in return for being allowed to come back).
McMahon's feud with Triple H was largely due to Triple H drugging Stephanie and using ventriloquism to trick a minister into marrying them. They had a no holds barred match at Armageddon which Triple H won. After the battle Stephanie turned on her father causing McMahon to leave for a while as he could not bear seeing his daughter married to Triple H.
When McMahon finally returned he helped the rock earn his title shot back from Big Show. During the fatal 4 way between Rock, Cactus Jack, Big Show and Triple H for the championship McMahon turned heel by betraying Rock and helping Triple H retain the gold.
McMahon took part in a 6 man tag team match partnering with Triple H and Shane against Rock, Kane and Undertaker in which whoever pinned their opponent would be named champion. Rock pinned McMahon and won the belt from Triple H. McMahon fought Kurt Angle but the match was rendered a no contest when Commissioner Mick Foley interfered to attack both men. After this both Angle and McMahon laid a beating on Foley and McMahon fired him. McMahon emotionally abused his wife Lind and began a public extra marital affair with Trish Stratus.
McMahon mistreated Trish as well as Linda as he forced her to bark like a dog and poring sewage on her before adding that Stephanie would always be daddy's little girl where as she was just "daddy's little toy". Vince's treatment of his wife prompted Shane to turn face in defense of his mother and challenged his father to a match at WrestleMania 17.McMahon had Triple H attack his son and accepted Shane's challenge. Shane also revealed that he had bought WCW from under his father's nose. Shane won the WrestleMania match against his father after Linda lashed out because of her husband's abuse and attacked Vince.
On the same night McMahon aided Austin in defeating the rock for the wwe title and formed a partnership with Austin. The partnership was short-lived as Austin betrayed McMahon to join the alliance (an alliance between the wcw and ecw wrestlers). McMahon became a face due to this angle as he opposed wrestlers who the fans were supposed to hate however once the matter was resolved he quickly returned to heel status.
McMahon would use threat of suspension to force wrestlers to kiss his ass but these segments were ended by Rock when he made McMahon kiss Rikishi's buttocks. McMahon was later in a feud with Ric Flair which he won. McMahon also feuded with Hulk Hogan as he took credit for Hogan's success and helped Rock beat Hogan in a match. They fought at WrestleMania 19 in a no hold barred match that Hogan won. McMahon fired Hogan who returned under the guise of Mr. America only to be fired again.
McMahon asked Stephanie to quit her job as smackdown general manager which she refused to do. McMahon then made an I quit match against Stephanie to force her out of her job at no mercy. On the same night McMahon interfered in a match between Brock Lesner and Undertaker for the wwe championship to help Lesner beat Undertaker, restarting the feud between McMahon and the dead man. They had a buried alive match at No Mercy, which McMahon won with help from Kane.
Despite often being represented as a villain McMahon was portrayed as a victim in 2009 when Randy Orton targeted the family members of Triple H. During 2010 when Bret Hart returned he called out McMahon, hoping to make peace but McMahon attacked him and continued to blame him for the events of survivor series 1997. McMahon would not accept Hart's challenge to fight him at WrestleMania but suddenly changed his mind after Hart's leg was broken. McMahon gleefully accepted Hart's offer of a no holds barred match but Hart revealed he had feigned injury to trick McMahon into agreeing to the fight. At WrestleMania 26 McMahon was defeated by Hart.
McMahon's appearances became more sporadic after money in the bank during 2011 when he unsuccessfully tried to prevent Cm Punk from leaving the wwe in a repeat of the Montreal screw job, only for his plan to be ruined by John Cena's sense of fairness. Despite this McMahon occasionally returns and has used his power to make things more difficult for guys like Daniel Bryan and Kofi Kingston.