3 WWE Superstars who signed 10-year contracts and 2 who signed for 15+ years

WWE Superstars’ careers are largely dependent on fan reactions and their ability to maintain a connection with audiences for as long as they are booked to appear on television.

The term ‘shelf life’ is often used when a WWE newcomer begins to gain momentum, such as when James Ellsworth suddenly became one of the most popular people on WWE programming in 2016.

At the time, WWE took advantage of his popularity by booking him in a storyline with AJ Styles and Dean Ambrose, but it was obvious to everybody that his shelf life as a WWE Superstar was going to be short-lived.

In stark contrast, there are certain people in WWE whose importance to the company is so great that they have been offered contracts for the next decade – or, in some cases, even longer.

In this article, let’s take a look at three WWE Superstars who signed 10-year contracts, as well as two Superstars who agreed to deals lasting at least 15 years.

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#5 Mark Henry (10-year WWE contract)

One of the first examples of Vince McMahon making a long-term commitment to a WWE Superstar came in 1996 when he offered Mark Henry a 10-year deal.

Henry, a passionate wrestling fan, had considered joining an NFL team after representing the USA as a powerlifter at the 1996 Olympics, but he was persuaded to join WWE following a meeting with McMahon at his office in Stamford, Connecticut.

McMahon agreed to pay Henry $250,000 per year for the next 10 years – a deal which, according to former WWE talent relations executive Jim Ross – caused a lot of problems for the WWE newcomer backstage.

“Well, there’s always jealousy. That’s what we’re talking about here, is basic jealousy. Insecurity and jealousy. So, I don’t know how you run your business, Conrad [Jim Ross’ podcast host, Conrad Thompson]. I know it’s successful, but I got a feeling you don’t put up with a lot of bull****. I didn’t have time for [talent’s] insecurities and your jealousy. Go to catering and get a table together, I don’t give a s***. You know, be an adult.” [H/T 411mania, quotes from Grilling JR]

In the end, Henry overcame the early animosity that his long-term WWE contract created for him. The Olympian continued to extend his deal with the company until officially retiring as an in-ring competitor in 2017.

Since then, the former World Heavyweight Champion has been inducted into the Hall of Fame, while he has also worked as a backstage mentor.

#4 The Big Show (10-year WWE contract)

Three years after Mark Henry signed a 10-year deal with WWE, a contract of the same length was given to The Big Show.

The former WCW World Heavyweight Champion made his WWE debut at St. Valentine’s Day Massacre 1999, where he interfered in the main event between Steve Austin and Vince McMahon.

A prominent Superstar in the Attitude Era, the man formerly-known as The Giant in WCW went on to feature in the main event of WrestleMania 2000 when he faced Triple H, The Rock, and Mick Foley in a Fatal 4-Way match.

Nowadays, The Big Show is regarded as a veteran of the WWE locker room due to his 21-year association with WWE, but it is worth remembering that he departed the company for one year between February 2007 and February 2008.

This meant that, unlike Mark Henry, the 7-footer did not stay with WWE for the entirety of his 10-year contract, although he has remained with the company for over a decade following his 2008 return.

#3 Randy Orton (10-year WWE contract)

Randy Orton has been regarded as one of WWE’s top Superstars for the majority of his career, so it should come as no surprise that the company wanted to secure his services on a long-term deal.

The man himself has admitted on numerous occasions that his attitude backstage landed him in a lot of problems in the early stages of his career, while Triple H said on the WWE Network series 'Ruthless Aggression' that Orton seemed “hellbent” on wasting his potential.

Thankfully, by 2010, “The Viper” had cleaned up his act and Vince McMahon rewarded him with a 10-year contract.

Since then, Orton has remained a key figure on WWE programming, particularly in 2013-2015 when he was involved in World Championship storylines with high-profile names including Daniel Bryan, John Cena, Batista, and Seth Rollins.

In more recent years, the former Evolution member has become a 13-time WWE World Champion – with his latest title victory coming against Bray Wyatt at WrestleMania 33 – and there is still plenty of time for him to potentially break Cena and Ric Flair’s record of 16 world title reigns.

#2 The Undertaker (15-year WWE contract)

In 2019, speculation about The Undertaker’s WWE future gathered pace after he was booked for a meet-and-greet session at Starrcast – a wrestling convention that had a minor affiliation with AEW.

As The Undertaker explained in his WWE Network docu-series 'Undertaker: The Last Ride', he had no reason to want to leave WWE, so he did not think the booking would cause a problem.

Vince McMahon had a different opinion, however, and he removed the legendary Superstar from the event, causing a brief fallout between the two men.

"Vince and I had a little bit of a falling out over it, and I understand where he was coming from. He’s got a business to run. I understand his position. But I also had a position of my own that needed to be understood. We didn’t talk for a little while and then we both let our guard down enough to talk and then we got things worked out.” [H/T Fightful]

It was also reported by the Wrestling Observer’s Dave Meltzer that Vince McMahon did not want The Undertaker to agree to any non-WWE bookings, which is why he handed him a 15-year contract in 2019.

#1 Bret Hart (20-year WWE contract)

To recap, Mark Henry and Randy Orton remained with WWE for their entire 10-year contracts, while The Big Show left the company two years before his long-term deal was originally due to expire.

In Bret Hart’s case, he was given a 20-year contract by WWE in October 1996 but he did not come anywhere close to completing that extraordinary deal.

Due to WWE’s struggles and WCW’s financial power, Vince McMahon was unable to honor Hart’s contract and he allowed his Superstar to negotiate a deal with the rival promotion in 1997.

This led to “The Hitman” leaving WWE to sign a contract with WCW that was reportedly worth around $3 million per year for three years.

Hart’s departure resulted in one of the most controversial moments in WWE history, and he admitted in 2020 on an episode of WWE Backstage that he wishes he never joined WCW.

“If I could do it all over again, I think I’d try to figure out a better way to stay in WWE. Knowing what I know about WCW, I’m sorry that I ever went there.”

Hart had problems with WCW producer Eric Bischoff during his time with the company, while he has repeatedly criticized Goldberg in recent years for hitting him with a botched kick that ended his career.