Vince McMahon has consistently been the most powerful and important person in the wrestling industry. WWE has been the top dog for most of the past few decades. McMahon took WWE to the top in the '80s and have remained in that spot until this day aside from under just two years when WCW took over. The wrestlers to join WWE must impress McMahon to get a push to the top. Almost every main event Superstar made Vince happy as performers. Not everyone has that luck and it has led to quite a few instances of wrestling struggling with McMahon.

We will look at both sides of the coin with wrestlers and their relationships with McMahon. Many wrestlers love the world of WWE and enjoyed the working relationships they formed with McMahon during their time there. Others failed to connect with Vince and truly loathed their time in WWE because of him. Both sides of wrestlers have valid points regarding why they feel the way they did when interacting with McMahon. WWE truly is a unique place, that leads to many differing opinions from the superstars that wrestled working for Vince.

Find out just which wrestlers strongly disliked spending time working for WWE and which absolutely loved it. These are ten wrestlers that regretted working for Vince McMahon and another ten wrestlers that adored working for him.

20 Regretted it: Neville

Neville is one of the few current wrestlers that made the decision to leave WWE due to his unhappiness with the company. The incredible in-ring work of Neville has always been impressive, but there was not much opportunity to move up the rankings in WWE’s pecking order.

A disappointing couple of losses to Enzo Amore led to Neville requesting his release from the company, knowing he did not fit in there. Sami Zayn appeared on Chris Jericho’s podcast recently and revealed that Neville did not enjoy the political landscape of WWE. Neville is clearly not someone that can be happy in a company run by Vince McMahon, which led to him requesting his release.

19 Loved it: The Miz

The Miz is one of the favorite wrestlers of Vince McMahon for good reason. Miz has done more media appearances to represent WWE than any other current WWE star. Miz's loyalty to the WWE is second to none. McMahon always saw something special in Miz, even when everyone wanted him fired.

The Miz’s first WWE Championship win in 2010 came as a decision from McMahon. No one expected him to reach that spot, but Vince believed in him. Miz has enjoyed his time in WWE more than most and wants to spend the rest of his career there. McMahon will likely try to keep Miz in the company in some capacity even when he does retire from the ring.

18 Regretted it: Shane Douglas

Shane Douglas was viewed as a great prospect in the early '90s. The talent of Douglas earned him a shot in WWE during a rebuilding process. Vince McMahon wanted to build new stars, but he often stuck wrestlers with over-the-top gimmicks. Shane was given the Dean Douglas gimmick to use his teaching background as a heel character.

Douglas hated his time in WWE and often trashed Shawn Michaels and the Kliq for burying him. The WWE run of Douglas ended shortly and he started ripping them in ECW promos. One complaint was that McMahon was a terrible boss. Douglas had no interest in ever returning to WWE and burnt all bridges after leaving.

17 Loved it: Ric Flair

Ric Flair is remembered for his run in WCW way more than the WWE run. WCW's demise made Flair strongly dislike his time there. Flair has gone on the record that his main regret from his career was not spending more time in WWE. The first run in the early 90s was a tad disappointing, but he enjoyed it more than the final run in WCW.

Flair developed a close relationship with the McMahon family. Despite his best work coming in WCW, Flair believes Vince McMahon was his best boss. Vince reportedly went out of his way to help Ric during some of his tougher times outside of the ring after his retirement.

16 Regretted it: Austin Aries

Austin Aries is currently a free agent on the independent circuit after a main event run in Impact Wrestling during 2018. It wasn’t too long ago that Aries was in WWE as he was released back in 2017 after spending time in NXT and 205 Live.

Aries had a negative reputation with the writers and certain important people backstage for how he carried himself. Vince McMahon’s company is not meant for everyone, as many wrestlers will find unhappiness working there. Aries is one that could not fit in and his attitude did not allow him to find success in WWE.

15 Loved it: Kurt Angle

Kurt Angle has had an up and down relationship with WWE. The early years featured a rise unlike anyone other as Vince McMahon loved his work. There were reports of Angle being Vince’s "favorite" wrestler to watch perform during a time with Steve Austin, The Rock, Triple H and other major stars in the company.

Angle left the company after refusing to clean up his life. There was a lot of hostility from Angle towards McMahon during his first couple of years in Impact Wrestling. Angle regretted leaving and insulting McMahon. The return to WWE for his Hall of Fame induction and beyond is the storybook ending for Angle getting to end his career working for Vince.

14 Regretted it: Vader

Vader was supposed to be a huge star for WWE when he made the move there in the mid-'90s. The success of Vader as a top main event heel for WCW in the early '90s gave hope to wrestling fans that he would thrive in WWE. Vince McMahon had an appreciation for the bigger wrestlers that portrayed monster heels.

Things, however, did not work out for Vader. McMahon did not like his wrestling style or look as a performer. Vader’s plans for a main event run ended with mostly mid-card work. Working for Vince was not for him as his best work came in WCW and New Japan.

13 Loved it: Mark Henry

Mark Henry is one of the few wrestlers to spend over two decades in the WWE. Vince McMahon personally reached out to sign Henry due to his success in the Olympics representing the United States. Henry received a push to start, but it took him a long time to get ready for a top role.

It wasn’t until over a decade later that Henry would emerge into an upper-level performer. Henry credits McMahon for helping him learn and grow as a performer. The career of Henry allowed him to become a Hall of Famer and a true WWE legend, as his time in the ring has unofficially ended.

12 Regretted it: Ryback

Ryback has been vocal about his WWE experiences and the negative moments that made him want to leave. Vince McMahon did push Ryback to the moon with a huge undefeated streak. Ryback had chances to become a main eventer against CM Punk and John Cena, but he failed to improve to their level.

There is blame towards McMahon for the lack of success from Ryback’s behalf. Ryback said on his Conversation with the Big Guy podcast that McMahon is not the best person to work for. He claimed that Vince would berate him and give advice that did not lead to much success. Ryback claims he has no interest in ever returning.

11 Loved it: Bret Hart

Many people assume Bret Hart hated working for Vince McMahon due to how things ended with the Montreal Screwjob. Hart actually had a strong love for McMahon as a boss until things went sour. Most of Hart’s WWE run featured McMahon giving him great opportunities and loving his work ethic.

Bret has stated in interviews that he viewed Vince as a second father figure. The Montreal Screwjob hurt him even more personally due to how much he loved working for McMahon. Hart has revealed that he regretted working for WCW and that he wishes he stuck around in WWE for the remainder of his career.

10 Regretted it: CM Punk

The ups and downs of CM Punk in WWE ultimately ended with him leaving in one of the ugliest departures in quite some time. Punk just did not like the way WWE was run. Vince McMahon had a positive personal relationship with Punk, but the way WWE was set up to run was not ideal for someone like Punk.

There were many instances of Punk having heat in WWE or speaking out about his unhappiness. The writing was on the wall that things would implode at some point. Punk likely respected and enjoyed McMahon at times, but the working standards led to him wanting to get out of there as soon as possible.

9 Loved it: Chris Jericho

Many wrestling pundits felt that Chris Jericho signing with WWE in 1999 was a huge mistake due to Vince McMahon not usually liking smaller wrestlers. Jericho, however, would work his way to the top within a couple of years. The relationship between Jericho and McMahon took some time to develop.

Jericho revealed that McMahon frequently buried him backstage during his first year, but it helped figure what changes needed to be made. The two would become very close throughout the years. Jericho credits Vince as one of the most important people that he met in his life. He even called McMahon to get his approval before going to New Japan.

8 Regretted it: Scott Steiner

Scott Steiner was considered a massive signing for WWE in 2002. The main event run of Steiner in WCW allowed him to have huge name value when the company ended, and he made his way back after a year letting his contract run out. WWE signed Steiner with huge plans.

Steiner’s first storyline put him against Triple H in the World Championship picture. Their matches were very awkward, and Steiner lost all momentum as he moved lower down the card. Interviews from Steiner today still feature him burying Vince, Triple H, and Stephanie. Scott even turned down a legends contract due to never wanting to work for WWE again.

7 Loved it: R-Truth

R-Truth was one of the unlikely favorites of Vince McMahon when he returned to the company in 2008. WWE hired R-Truth for mid-card depth after he became a top talent for TNA with his rapping skills. McMahon enjoyed the likability of R-Truth and used him longer than most expected.

R-Truth is still getting television time with Carmella as the Mixed Match Challenge winners and is currently the 30^th entrant in the Royal Rumble match. McMahon even used him in a few major main event matches during The Rock and John Cena storyline. R-Truth has accomplished a lot and continues to enjoy working for Vince.

6 Regretted it: Paul London

Paul London was the original big independent wrestling star to sign with WWE in the early 2000s. Ring of Honor had London as one of their major stars in the early years. WWE took note of London’s talent and signed him. London found success in the cruiserweight and tag team divisions, but neither led to a long-term role.

The WWE climate was not for London as he hated the political landscape. Vince McMahon, specifically, is someone that London criticizes for his interactions with him. London even intentionally smiled during a serious segment that featured McMahon walking past the entire roster before his limo exploded because he didn’t care about getting fired.

5 Loved it: The Undertaker

The Undertaker is one of the top wrestlers to have a tremendous relationship with Vince McMahon throughout the years. Considering the Phenom has been a part of WWE for almost thirty years now, there’s a strong level of respect on both sides with McMahon.

The Undertaker has long served as a locker room leader during a few different eras. McMahon will likely allow Undertaker back if he wants to continue wrestling for as long as he wants. Undertaker will always have a home in WWE even when he does hang them up. This is one legend that truly loved working for Vince in WWE.

4 Regretted it: Gail Kim

Gail Kim has been vocal about how much she disliked working for Vince McMahon whenever she is asked about it. The legendary women’s wrestler had her best work in Impact Wrestling, where she became their first female Hall of Fame inductee. This is regretful for us all since she had two runs in WWE and they refused to anything of note with her.

Kim returned a second time to WWE after success in Impact with hopes of a better run. WWE used her even worse this time around. Gail claimed that Vince was very disrespectful towards her and it led to a horrible time in her career. Even with the changes for the women’s division, Kim has zero interest in ever doing anything with WWE if McMahon is still there.

3 Loved it: JBL

There has been a running joke in WWE for many years that JBL is the real-life version of a puppet for Vince McMahon. Between his appearances on talk shows and his WWE commentary, JBL often recites things that McMahon strongly believes. The burials of WCW talents, jokes about Jim Ross, and other things we’ve heard from JBL often parrots McMahon.

Jimmy Jacobs revealed on Colt Cabana’s podcast that he would see JBL do the same thing backstage. McMahon did view JBL as one of his most loyal employees after a very long run in WWE. JBL received the most random title reign until Jinder Mahal due to Vince believing in him, and unlike Mahal, he was able to sustain his main event push for a few years. This is one wrestler that clearly loves McMahon.

2 Regretted it: Rob Van Dam

Rob Van Dam achieved great success in WWE and was arguably the most successful ECW wrestler to make the jump. Despite getting over with the fans and making a great living, RVD did not enjoy his time working for Vince McMahon. Various interviews from Van Dam featured him admitting he was never happy in WWE due to how political it was backstage.

RVD is one wrestler that did not care for McMahon and the WWE landscape, but it was the only major promotion. Van Dam is still adamant that ECW was the best time of his career and he wishes he could have wrestled there forever.

1 Loved it: John Cena

The relationship between John Cena and Vince McMahon became very close due to how much they meant to each other. Cena was the face of WWE for a decade. McMahon has never put that much faith into another wrestler, as Hulk Hogan and Steve Austin both saw their runs end earlier.

The loyalty and work ethic of Cena each made him the perfect wrestler for McMahon. Until Roman Reigns' arrival, no one could surpass Cena in Vince’s eyes, which is why he remained on top for so long. Cena loves the WWE environment more than any other wrestler and will likely be part of the WWE family for the rest of his life even as he goes into Hollywood.