#5 Ultimate Warrior

Love him or loathe him, the Ultimate Warrior will go down as one of the legends of the squared circle. Despite being sort of limited inside the ring, the Warrior still made it to the top of the business, including beating Hulk Hogan in the main event of WrestleMania 6.

However, as Warrior became a bigger draw, there was friction with Vince McMahon regarding money. Things came to a head after WrestleMania 7, where Warrior faced and beat the Macho Man. Warrior felt that he was owed more than WWE paid him and he sent a handwritten letter to Vince McMahon demanding a payment of $550,000 as well as a cut of the gate in a similar percentage to what Hulk Hogan was getting. Here’s what Warrior said in the note:

Vince McMahon initially agreed to Warrior’s demands but ended up suspending him after the SummerSlam PPV a month later, claiming that Warrior was hard to work with. Warrior ended up quitting and later suing WWE, although the two sides would settle their differences briefly. This led to another lawsuit from Warrior in 1993.

Warrior ended up going to WCW for a bit but this run was a total failure. Warrior’s relationship with WWE only to a turn for the better in 201 when he was inducted into the WWE Hall of Fame. He also appeared on WrestleMania and RAW on the following night. The Ultimate Warrior passed away on the following day.

#4 Jesse Ventura

Taking Vince McMahon to court isn’t what one would call a good idea. In fact, very few have taken Vince to court and won. One of the few who have sued McMahon and have come out on the winning side is Jesse ‘The Body’ Ventura.

The story starts in 1987 when Ventura was renegotiating his contract. At the time, Ventura was told that non-performers don’t get royalties for videotape sales and thus he waived his rights to royalties for them.

When Ventura later found out what he had been told about non-performers not getting royalties was false, he took McMahon to court. Ventura demanded $2 million in royalties. The case went to federal court and McMahon was ordered to pay Ventura $801,333 as well as $8,625 in back pay. At the time, Vince McMahon said that Ventura would never appear on WWE television again but he actually did appear a few times over the following years.

Ventura spoke about taking Vince McMahon to court in an interview years later, talking about his departure from the WWE:

#3 Bruno Sammartino

An icon in professional wrestling, Bruno Sammartino held the WWWF Championship for 11 years across two reigns. His first reign as champion clocked in at 2803 days, which is still the longest WWE title reign and its unlikely that it will ever be eclipsed.

After leaving the WWWF in 1981, Sammartino learned that Vince McMahon Sr had paid him a lesser amount of the gate than he was entitled to during his entire second title run. Sammartino settled his dispute when Vincent Kennedy McMahon took over and returned as a commentator in 1984. However, Sammartino was upset with the direction Vince McMahon was taking the company and left in 1988. In a later interview, Bruno said that he was upset with the widespread use of steroids in the company at the time:

Bruno Sammartino was inducted into the WWE Hall of Fame in 2013.

#2 Nailz

Kevin Wacholz, aka Nailz, wrestled for WWE in the early 90s. He was portrayed as an ex-con who had once been an inmate at a correctional facility where the Big Boss Man worked. There were rumors at the time that Nailz was set to feud with The Undertaker, but it all came to a stop after an altercation with Vince McMahon backstage after being upset with his push or lack thereof.

Jim Ross, who described Nailz as “unstable” described the incident on his podcast:

This led to Vince McMahon firing Nailz. Both Nailz and Vince McMahon later sued each other, although nothing ever came of either lawsuit.

#1 CM Punk

CM Punk is one of the biggest stars WWE created in the last decade. His unceremonious departure in 2014, saw him go on try his hand at UFC which was a failure. He hasn’t returned to the WWE ring since.

What made Punk’s departure more complicated was WWE sending him termination letter on the day of his wedding to AJ Lee. Punk also criticized WWE doctor Dr. Amann and the treatment he received while injured.

Punk criticized WWE and even Vince McMahon himself on Colt Cabana’s podcast:

Punk hasn’t returned to the WWE ring since his departure although he was recently a part of WWE Backstage which was recentlycanceled by FOX.

Which of Vince McMahon’s feuds did we miss out on? Sound off in the comments section.

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