The process of working for WWE is not always the easiest task with Vince McMahon as your boss. A select few wrestlers do earn the trust of McMahon right away with John Cena, Roman Reigns and Brock Lesnar all benefiting from the perk. However, the path for some top stars will see them have to win over the boss before getting to the top of the mountain.
These wrestlers did not connect with Vince right away and it showed in the booking. Their process in WWE took quite some time before gaining the trust needed to succeed. McMahon eventually saw what they offered, and they would have strong runs with the company. The timetable for winning over Vince ranged from a few months to many years as some played the long game. Find out just which talents had to prove something to the boss as these ten wrestlers won over Vince McMahon with time.
10 CM Punk
The WWE career of CM Punk took some time before he started gaining momentum. Triple H, Shawn Michaels and other major names reportedly had an issue with Punk due to his look and unconventional wrestling style.
Vince McMahon eventually was the one to believe in Punk ahead of his first Money in the Bank win. Punk won the contract twice to become the WWE Champion and World Champion in back to back years.
The summer of Punk changed WWE forever thanks to McMahon allowing Punk to have freedom in his promos. Punk was viewed as having a good relationship with Vince but tension with Triple H at the end.
Tazz was one of the biggest ECW stars to make the move to WWE in 2000. A tremendous debut would see Tazz force Kurt Angle to submit in front of a red-hot crowd at Madison Square Garden. Unfortunately, Vince McMahon ended his push that night due to viewing Tazz’s suplexes as dangerous.
WWE jobbed out Tazz to the lower tier of the card until he started doing broadcasting work on Sunday Night Heat. McMahon enjoyed Tazz’s style as a personality and moved him to the commentary table as injuries slowed down his in-ring career. Tazz became one of the top commentators in WWE history.
8 Chris Jericho
The relationship between Chris Jericho and Vince McMahon got off to a bad start in the first few months. Jericho struggled to adapt to the new world of WWE in terms of both the in-ring style and the locker room.
According to Jericho’s book, McMahon ripped him apart backstage after a few weeks claiming he was not worth the paper he signed his contract on. Vince even made Jericho work with X-Pac solely to learn from him. Jericho would eventually catch fire with momentum, become one of the top stars in WWE history, and he developed a bond with McMahon.
7 Bray Wyatt
Bray Wyatt’s look in general has not made him the typical wrestler that Vince McMahon wanted to push in WWE. The first few months of Wyatt’s run featured him rarely wrestling as Luke Harper and Erick Rowan did the physical stuff as Bray cut the promos.
McMahon was hesitant about pushing Wyatt until the character work sold him. Bray’s Firefly Fun House skits have featured a Vince puppet running him down which references some of the past differences. Wyatt is clearly on McMahon’s good side now as a top act in the company as The Fiend.
6 Paul Heyman
The relationship between Paul Heyman and Vince McMahon has seen many ups and downs throughout the years. McMahon helped Heyman out when the latter ran ECW by providing some money and having some of his contracted talents work for the company.
Even the working relationship between them in WWE had low moments as they had a huge argument before Heyman left the company following the ECW relaunch. This most recent return has seen Heyman earn Vince’s trust as he now has the most control when putting together Raw every week.
The first stint of Goldberg in WWE was a huge disappointment. Vince McMahon didn’t care for Goldberg’s WCW gimmick of beating wrestlers within a handful of minutes. Goldberg entered feuds with Chris Jericho and Triple H in matches that went way longer than ideal for him.
McMahon believed all main eventers and world champions should be able to have longer matches since that’s a house show duty for the role. Goldberg left after a year and didn’t return until over a decade later. Vince understood Goldberg this time around and he had a way better run with shorter matches.
4 Daniel Bryan
Daniel Bryan’s first night in WWE for the original NXT featured a great match against Chris Jericho, but Vince McMahon was not sold on him. Jericho claimed he told McMahon that Bryan was a star and McMahon responded by saying he’s too small along with some critical comments about his vegan lifestyle.
Bryan would win over Vince in small doses throughout the year. The first major accomplishment came with a World Championship reign, but he did lose it in embarrassing fashion to Sheamus at WrestleMania 28. Fans rallying for Bryan got him to the main event of WrestleMania 30 where he earned a spot in the main event scene for good and McMahon was all for it.
3 AJ Lee
WWE typically hired models for the women’s division throughout the 2000s and early 2010s. AJ Lee was one of the rare hires with a wrestling background. According to her book, Lee claimed that WWE management told her she was not on television due to not being desirable to the male audience.
Vince McMahon likely was one of the people to have this belief, but it clearly changed once she got her first real opportunity. Lee became a fan favorite and the most relevant woman in the division. The trust of McMahon was earned to the point that he allowed her to cut her “pipe bombshell” promo ripping apart Total Divas without a script.
Despite his love of Edge, Vince McMahon did not view Christian as a star for many years. A former WWE writer claimed that McMahon hated the look of Christian and once pitched the idea of editing a giant blue dot over his face while wrestling or cutting promos.
The return of Christian to WWE following his TNA stint did not see much change right away as he was slotted on the lower tier ECW show. Christian did a good enough job on the show to eventually win over Vince. The World Championship reigns of Christian came in 2011 along with a memorable top feud with Randy Orton.
1 Mick Foley
The hiring of Mick Foley to WWE in the 90s seemed like a no-brainer on paper looking back at his success. Vince McMahon however did not want Foley on the roster. Jim Ross was allowed to hire Foley in his new backstage role as Vince wanted to learn a lesson on having a talent break your heart.
Foley did not allow McMahon’s vision to come true as he hit a home run with the Mankind gimmick. A tremendous feud with Undertaker won over Vince right away. Foley found more success as he also played Dude Love, Cactus Jack and his real persona to become a top part of the Attitude Era.