The art of negotiation is probably the most important aspect of business for a wrestler. Talent will discuss contract details with promotions before agreeing to a deal. Wrestlers always have the ability to shut down a contract if it looks bad. Promotions have the ability to do the same in finding the best deal for their company. Both sides would benefit from a great deal that leads to success for everyone involved. Horrible contracts typically see one of the two parties suffering for it, usually the promotion overpaying someone or giving out too many perks.

The Monday Night Wars was the absolute best time for a wrestler in the United States looking to make a great living. Two promotions at war with huge money and massive television deals gave the wrestlers leverage to hold out for the best deal. This is why the majority of wrestlers worked for both WWE and WCW throughout the 90s. There were many staggering contracts given out that look rather shocking today. Great contracts would see wrestlers take a decent deal making a good living before blowing up into a top level main event star with a pay raise. Horrible contracts were the ones that led to noteworthy negatives. We'll look at both sides with the ten worst wrestling contract in the 90s along with the five best.

15 15. Worst: Bret Hart - Both WWE & WCW Contracts 

WWE and WCW both gave out contracts to Bret Hart that they would end up regretting. Hart was definitely one of the biggest stars of the era, but the competition between the two companies led to them overpaying him. WWE signed Bret at the peak of his popularity in 1996 to a ridiculous 20-year contract making $1 million+ each year.

Vince McMahon eventually regretted such a contact and told Hart WWE couldn’t afford to pay him any longer about a year later setting up the events of the Montreal Screwjob. WCW signed Bret once he was out of WWE to a contract worth $2.5 million per year. Hart could have contributed to WCW in a major way but the company had no idea how to use him. Most fans forget the WCW chapter of his career that ended it all in depressing fashion due to injury.

14 14. Worst: Disco Inferno - WCW Contract 

The biggest reason WCW went out of business in such quick fashion following their success was due to all the money they wasted. Eric Bischoff was using Ted Turner’s checkbook and gave massive contracts to anyone leaving WWE. WCW decided to shell out one of these horrible contracts to a homegrown guy when paying Disco Inferno the big bucks for the final three years of their existence.

Disco was a glorified enhancement talent that stood out somewhat for his humorous moments. Fans enjoyed laughing at Inferno and watching him get beat up. Clearly, he wasn’t valuable to the product in any way aside from filling time. WCW paid him between $300,000 and $350,000 during the last three years before selling to Vince McMahon. The company bled money and Disco’s contract shows why.

13 13. Best: Chris Jericho - WCW Contract 

Chris Jericho was one of the few stars being underpaid in WCW. Jericho did make a good living but the company held very little respect for him. The first autobiography of Jericho looking at his WCW career saw him explain that WCW would screw over him and the other mid-carders in residuals. Jericho recently posted a picture of an old check he received that featured his pay being less than a dollar and worth less than the stamp used to post it.

The decision of Jericho to leave WCW for WWE was a great business move. Jericho took a bit of a pay cut on the first contract but made up for it with opportunities that moved him up the card. Various perks and an increase in merchandise numbers helped Jericho make great money. The rest is history with Jericho becoming one of the wealthiest wrestlers in the following contracts. Great wrestlers should always bet on their talent as it pays off in the end (at least most of the time).

12 12. Worst: Brian Pillman - WWE Contract 

Brian Pillman was an underrated talent but WWE overpaid him big time when signing him away from WCW and ECW. The reputation of Pillman for being the “loose cannon” made his character a very intriguing one. WWE had to have Pillman so bad that they offered him the first guaranteed contract in company history. The salary of $300,000 was quite high for WWE at time; the guaranteed stipulation was the biggest shock.

Of all the wrestlers to work for WWE, no one would have guessed Pillman as the first to get this contract. WWE didn’t even use Pillman as a top star. Aside from a few controversial segments with Steve Austin designed to create publicity stunts, Pillman did nothing of note until joining The Hart Foundation as the fourth most important member.

11 11. Worst: Master P - WCW Contract

Some of the worst WCW contracts were actually given out to people from outside of the wrestling industry. Master P was a very popular rapper in the 90s and WCW decided to pay him huge money to try to make them “cool” again after WWE started to dominate the ratings war in 1999. WCW paid Master P almost $300,000 for a handful of appearances.

To make matters worse, WCW also paid the other rappers in Master P’s No Limit Soldiers that would travel with him to the show as his entourage. Fans booed Master P out of the building every week. Considering WCW was primarily located in Southern cities, the fans revolted against the rapper and cheered the country music heel West Texas Rednecks. WCW got nothing out of Master P’s contract losing money and credibility along the way.

10 10. Best: Mick Foley - WWE Contract 

ECW fans chanted “You sold out” at Mick Foley when he decided to leave the hardcore promotion for a better contract in WWE. While the pay was much better, Foley did not sign a massive contract by any means. According to Foley, it was more of an opportunity to have a great future while making a good living along the way.

Foley achieved great success with the Mankind character becoming a rare great opponent for The Undertaker in a long-term feud. Fans eventually fell in love with Foley due to his hard work and putting it all on the line. The fact that he had a genuinely likeable presence helped as well. Foley would become one of the highest paid stars in WWE towards the end of the 90s as a top guy. WWE made even more money off him allowing both parties to benefit greatly.

9 9. Worst: Lex Luger - WWE & WCW Contracts 

The physique of Lex Luger definitely is the main reason he became a very wealthy man in the wrestling industry. Both WCW and WWE viewed him as a cornerstone of building the company around. Luger’s first awful contract came from WWE in the early 90s when Vince McMahon brought him in to replace Hulk Hogan. McMahon wanted another muscle head to use the patriotic gimmick to bring in the money.

No one viewed Luger as anything more than another upper mid-carder and WWE was forced to change plans making his massive contract a mistake. Luger returned to WCW when becoming a free agent to get another fat contract. The salary of Luger ranged between $725,000 and $1.6 million each year with this contract. Luger made seven figures the final three years of his contract to deliver mediocre work and disappointing drawing power.

8 8. Worst: Big Show - WCW & WWE Contracts 

Big Show received two of the luckiest a contracts a wrestler will ever find in the world of wrestling. WCW signed him without any experience to feud with Hulk Hogan and win the WCW Championship. As the Giant, he made between $230,000 and $450,000 during his first three years in the business. That figure dropped in his final year before he made the jump to WWE.

Vince McMahon loves the big men and couldn’t resist the temptation of his athleticism to match it. Big Show signed one of the best WWE contracts at the time for ten years. The downside saw him make $950,000 each year of this contract. WWE dreamed of him being up there with Steve Austin, The Rock, Mankind and Triple H as a top guy. Big Show achieved a lot of success but was always below those names. As an upper carder most of his career, the contract he signed to start his WWE career is unbelievable.

7 7. Best: Diamond Dallas Page - WCW Contract 

WCW managed to find a good contract when giving a chance to Diamond Dallas Page. The contract of DDP saw him make a modest $150,000 in 1996 as he started work his way up the rankings. Page became a fan favorite and worked with top stars like Hulk Hogan and Randy Savage over the next few years. WCW ended up having to pay his worth of $365,000 in 1998 and $1 million+ for the final three years before they went out of business.

Unlike the other big names in WCW to make huge money, DDP actually worked for his by proving his value to the WCW fans. Page never created issues with other talent or did anything to hurt the company. A homegrown star doing what is best for business and becoming a main event star along the process proved he deserved his contract earnings more than most.

6 6. Worst: Tank Abbott - WCW Contract 

Tank Abbott was one of the first few UFC fighters to make the jump into professional wrestling during the 90s. WWE signed Ken Shamrock and it was a pretty good move considering he possessed some name value. Abbott however held a disappointing record of 2-5 in UFC but WCW felt he would be the right man to portray a top heel coming from the MMA world.

The original plan was for him to be the main rival of Goldberg as the end goal. WCW signed him to a foolish contract worth $650,000 per year. Abbott struggled to find relevance on the show and just couldn’t become a main eventer. Things worked out so badly that Abbott achieved his biggest WCW success as a backup dancer for the boy band faction 3 Count. At least he was able to make huge money for his dancing skills....

5 5. Worst: Ultimate Warrior - WWE & WCW Contracts 

The short-lived success as a top star in WWE during the 80s landed Ultimate Warrior a lifetime of riches. Following his WWE Championship reign flopping, Warrior would have a horrible time finding success in the ring for the rest of his career. Fans still loved cheering him but he just was no longer a top guy which is how he viewed himself.

WWE paid Warrior a lot of money to return to the company in the mid-90s when looking for familiar faces to fill the gap after Hulk Hogan left. Warrior often no-showed events and displayed little respect for his peers. WWE grew sick of him but Warrior would find another promotion to disappoint. WCW paid Warrior $1 million upfront to appear for a storyline with Hogan. The two former rivals had one of the worst matches in wrestling history and Warrior was out of the company after a few appearances. It's almost impressive that Warrior found the easiest way to make a million bucks.

4 4. Best: Booker T - WCW Contract 

Most of the top WCW stars were handed huge contracts thanks to their past success in WWE. Booker T is the best story of someone working their way up the card and giving the company an unexpected star. The salary of Booker was just $150,000 in 1996 as a tag team wrestler teaming with Stevie Ray in Harlem Heat.

Booker started to shine as a singles star in 1997 and 1998. By 1999, Booker was one of the most popular faces in WCW. The contract would rise to $640,000 and $740,000 in 1999 and 2000 with Booker cashing in on his hard work. It was only fair WCW paid Booker his worth after receiving many years of underappreciated work. The work ethic of Booker landed him another decade of success in the industry mostly coming from great pay days in WWE.

3 3. Worst: Mark Henry - WWE Contract 

WWE made a bold move in 1996 going after Mark Henry. Despite having no wrestling experience, WWE signed him to a surprising ten-year contract with a $250,000 guaranteed downside. Henry had a background in weightlifting that landed him on the United States Olympic team. WWE hoped to cash in on his success in his prior worlds.

Many WWE stars disliked Henry for being slow in learning the art of wrestling while having a contract significantly better than theirs. Henry often spent time off television in developmental and didn’t make a true impact at the top of the card until 2011. The entire decade of the original contract was a huge bust. Henry showed why a wrestler should have some experience before you give them the big money.

2 2. Worst: Hulk Hogan - WCW Contract 

Hulk Hogan leaving WWE for WCW saw him sign one of the most ridiculous contracts in the history of any sports or entertainment world. The star power of Hogan made him between $1.9 million and $4.6 million every year in WCW. That isn’t too bad considering his presence in the company leading the New World Order started the new boom period. The problem was Hogan had too many perks in the contract.

Hogan had a creative clause that allowed him to shut down any ideas he didn’t agree with. That is the main reason you rarely ever saw Hogan lose a big match and there often shenanigans involved when he did lose. Hogan also received a 15% bonus of sales for each PPV he wrestled on and 25% of gross tickets sold for every television episode he delivered a promo on. WCW even paid him an extra $20,000 to wear nWo shirts in magazines. No one ever did more damage to a promotion with a contract than Hogan did to WCW.

1 1. Best: Steve Austin - WWE Contract 

The original WWE contract of Steve Austin turned out to be one of the best decisions for both a wrestler and a promotion. WWE took the chance on Austin after he ditched WCW and was having an impressive run with ECW. Austin worked as The Ringmaster making mediocre money for a television wrestler until he started to develop the “Stone Cold” character.

A low level contract would turn into Austin becoming one of the richest stars in wrestling history. Austin led the Attitude Era as WWE made more money than ever. Following the start of his run as the top star in 1998, Austin made between $5 million and $12 million every year. The craziest thing about this is that WWE made even more off his name. Austin signing for low six figures blossomed into him making over $10 million in multiple years proving a modest contract can lead to so much more.