Sheep, Jell-O, and the Most Ridiculous Contracts in Sports History

Colin Ward-HenningerContributor IMarch 31, 2017

Sheep, Jell-O, and the Most Ridiculous Contracts in Sports History

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    When there are top free agents on the market, the offseason can sometimes be as exciting as the season itself.

    Teams get into bidding wars for the biggest stars in the game, and most of the time it comes down to money. Contracts aren't all about money, however, and sometimes athletes demand perks to go along with their fantastic sums of cash.

    For some reason, it happens in baseball more than any other sport, but there are also contract clauses in other sports that leave you scratching your head.

    Here are the 20 most ridiculous contracts in sports history.

    Be sure to follow me on Twitter @CWardHenninger

20. Kevin Brown (Los Angeles Dodgers)

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    Kevin Brown established himself as the top pitcher in baseball after three great seasons from 1996-98, culminating with a trip to the World Series in 1998 with the San Diego Padres.

    When he came up for free agency at the end of the season, everyone knew he was in for a big payday, and the Los Angeles Dodgers won the bidding war.

    They made Brown baseball's first $100 million man (a number which seems minuscule by today's standards), with a seven-year, $105 million contract.

    Besides the tremendous amount of money, Brown's contract included one of the more ridiculous clauses in baseball history:

    The Dodgers agreed to charter a jet to fly Brown's wife and children from the family's home in Macon, Ga., to Los Angeles 12 times a season.

    I guess that $105 million wasn't enough to afford plane tickets.

    Brown had a few solid seasons before injuries ruined his career, and he was eventually traded to the Yankees, where he angered New York fans for the last two years of his contract. 

19. Curt Schilling (Boston Red Sox)

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    Red Sox pitcher Curt Schilling, of bloody-sock fame, was nearing the end of his career before the 2008 season, but the Red Sox were willing to give him one more year.

    Since Schilling was 41 years old, the Red Sox created a one-year, $8 million contract that was laden with incentives that could potentially allow Schilling to earn a lot more money.

    One incentive in Schilling's contract promised to pay him $2 million if he met certain pre-arranged weight requirements established by the organization.

    Basically Schilling would be paid millions of dollars for not sitting on the couch and eating cheeseburgers in the offseason. Unfortunately, the plan didn't work, and Schilling never pitched another game in the big leagues.

18. Mark McGwire (St. Louis Cardinals)

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    When slugger Mark McGwire was traded to the St. Louis Cardinals at the MLB All-Star Break of the 1997 season, he instantly became a fan favorite.

    The Cardinals had to negotiate a contract in the offseason to keep McGwire, and they ended up signing him to a four-year contract worth nearly $40 million. That was a lot of money in 1998, but McGwire made a shrewd business decision by including the following clause:

    McGwire received an attendance bonus of $1 per fan for each Busch Stadium fan beyond 2.8 million for each year that he played in St. Louis.

    This seemed reasonable for the Cardinals, which had drawn just 2.4 million fans in 1997, the year before the contract kicked in. But McGwire knew something special was in store.

    Of course, we all know that in 1998 McGwire went on a home run tear, battling the Cubs' Sammy Sosa in a chase for the all-time single-season record.

    McGwire ended up setting the record with 70 homers that season, and the Cardinals drew 3.2 million fans, which earned Big Mac a bonus of around $400,000. The Cardinals drew well over three million fans every season that McGwire was there. 

17. Cristiano Ronaldo (Real Madrid)

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    When Real Madrid signed Portuguese superstar Cristiano Ronaldo to a six-year deal worth 80 million pounds (about $132 million), they wanted to make sure they held onto him for a long time.

    Real Madrid put a clause in Ronaldo's contract that if any team wanted to negotiate with him while he was still under contract, the bidding would start at 1 billion Euros. That's about 1.4 billion US dollars.

    I know there are some pretty rich clubs out there, but even Donald Trump would balk at the thought of paying that much money to negotiate with a player.

16. Carlos Beltran (New York Mets)

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    Carlos Beltran was one of the most coveted free agents in recent memory, and the Mets were thrilled to sign the young outfielder before the 2005 season.

    While you might think Beltran's seven-year, $119-million contract is on the list because of how poorly he has performed since signing it, Beltran actually had some solid years in the early days of his contract. He's on the list because of this interesting perk:

    As part of the contract, the Mets are required to lease an ocular enhancer machine, an eyesight and hand-eye coordinating device used for batting that throws numbered and multi-colored tennis balls at 150 mph, for Beltran's use.

    Unfortunately, the machine can't stop Beltran from getting hurt, as he has played a total of only 145 games in the past two seasons. 

15. George Brett (Kansas City Royals)

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    George Brett is the best player in Royals history, so in order for him to finish his career with the team, the front office was willing the give him anything he wanted.

    So when Brett signed an extension with the Royals in 1984, it included all sorts of bonuses, including guaranteed post-career employment with the franchise. But there were a couple of perks in there that were particularly odd:

    Brett negotiated that the Royals had to give him back the bat from the infamous "pine tar incident" that occurred on July 24, 1983, and he also earned part ownership of an apartment complex in Memphis.

    Just as a reminder, the Royals play in Kansas City, but then-owner Avron Fogelman owned a lot of property in Memphis, so it was only natural to throw a piece of it into the contract.

14. A.J. Burnett (Toronto Blue Jays)

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    Toronto has a tough time luring free agents. Not only do they play in the vaunted American League East against perennial powerhouses the Yankees and the Red Sox, but it's also hard to convince American or Latin players to come live in Canada.

    When starting pitcher A.J. Burnett signed with the Jays in 2006, he made sure that he would have his support system on hand.

    Burnett negotiated a clause in his contract where the Blue Jays would provide eight round-trip limo rides from Maryland to Toronto for his wife, Karen, and his children.

    Karen is apparently deathly afraid of flying, and insisted on taking the nine-hour limo ride instead of a two-hour plane flight.

    I've never met Karen Burnett, but if she can survive a nine-hour car ride with two toddlers, she deserves to win Woman of the Year.

13. Glen 'Big Baby' Davis (Boston Celtics)

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    Glen 'Big Baby' Davis got himself in great shape before the start of his NBA career and helped lead the Celtics to the 2008 championship and another NBA Finals appearance in 2010.

    When the Celtics re-signed him to a two-year deal before the 2009-10 season, they wanted to make sure that the guaranteed money didn't lead to Davis slacking on his workouts.

    Davis' contract reportedly contained a clause that said Davis would receive an extra $500,000 for each year of the deal that he remained under 310 pounds.

    Weight clauses are nothing new, but 310 pounds! How could a 6'9" NBA player who runs up and down the court for hours on end not stay under 310 pounds?

    Davis is officially listed at 289, so if he can just stop himself from putting on 20 pounds each season, he'll take home a million dollars.

12. Daisuke Matsuzaka (Boston Red Sox)

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    In 2006, MLB teams scrambled to get money together to pay for Daisuke Matsuzaka, one of the most highly-touted Japanese pitchers in baseball history. They weren't paying for his contract, though. They were paying for the right to negotiate a contract with him.

    The Red Sox won the right with a sealed bid of $51.1 million, and then the salary negotiations started. The Sox ended up signing Dice-K to a six-year, $52-million contract, but the Japanese ace wanted to make sure that the transition from Japan to Boston was a smooth one.

    Matsuzaka negotiated that the Red Sox were required to provide eight first-class round-trip airline tickets per year between Boston and Japan, a $75,000 Boston housing allowance, use of a Lincoln Town Car (or comparable vehicle), a personal masseuse, and the uniform No. 18.

    I guess it takes all the guesswork out of uniform number issues if you just put it in your contract that you have the right to a certain number.

    Unfortunately the number has been anything but lucky as Dice-K has been quite a disappointment as a member of the Red Sox. They did win the World Series in his first year with the team in 2007, however, so maybe he's more lucky than we thought.

11. Greg Maddux (San Diego Padres)

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    Four-time NL Cy Young Award winner and future Hall-of-Famer Greg Maddux is one of the greatest pitchers of all-time, so he had earned some negotiating power by the tail end of his career.

    In 2007, he signed a one-year, $10-million contract to play with the San Diego Padres, but there was one thing Maddux just had to throw into the deal.

    Maddux, an avid golfer, required the Padres to provide him a one-year membership at Del Mar Country Club, near San Diego.

    I'm surprised Maddux didn't require a gym membership as well. We know he likes to work out.  

10. Troy Glaus (Arizona Diamondbacks)

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    The Arizona Diamondbacks signed slugger Troy Glaus to a four-year, $45-million contract in 2004, even though he was coming off of a couple of injury-plagued years with the Angels.

    While the money might not have been as high as one might expect for a guy who had hit as many as 47 home runs, Glaus made sure to make the contract worthwhile by adding a certain perk:

    The Diamondbacks agreed to pay up to $250,000 a year to compensate Glaus' wife, Ann, for her equestrian training and equipment.

    Glaus hit 37 dingers for the Diamondbacks before being traded to the Blue Jays the following season. I'm sure Glaus made sure that the Jays would take on his wife's equestrian expenses as well.

9. Roy Oswalt (Houston Astros)

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    This technically wasn't in his contract to begin with, but his contract was later amended to include the deal, so it still belongs on the list.

    Roy Oswalt was the Houston Astros' franchise pitcher in 2005, and he was charged with leading his team to victory in Game 6 of the NLCS against the Cardinals.

    Astros owner Drayton McLane wanted to create a further incentive for his ace pitcher, so he promised Oswalt that if he won the game, McLane would buy him an all-purpose tractor (aka a bulldozer).

    I don't know how many pitchers would be motivated by something like that, but it sure seemed to strike the fancy of Oswalt, who was born and raised in Mississippi.

    Sure enough, Oswalt pitched brilliantly and won the game, sending the Astros to the World Series.

    A few days later, McLane made good on his promise and presented Oswalt with a brand new Caterpillar D6N XL, complete with Astros logos and a red bow on top.

8. Stefan Schwarz (Sunderland)

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    Swedish soccer player Stefan Schwarz signed a four-year, 4-million pound contract with Sunderland of the English Premier League in 1999.

    Occasionally, players get injured performing hobbies like skiing or hunting, so clubs tend to forbid this behavior in contracts. I'm sure Sunderland didn't expect to hear Schwarz's plans for the near future, but they went ahead and prohibited them anyway.

    Schwarz's contract with Sunderland stipulated that he was not allowed to travel into space while playing for the club.

    Apparently Schwarz had expressed a desire to be an astronaut after his playing career, so the club didn't want to take any chances.

7. Rollie Fingers (Oakland A's)

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    Oakland A's owner Charlie Finley was a consummate promoter, pulling off such stunts as implementing a mechanical rabbit to pop up and deliver new baseballs to the home-plate umpire and introducing orange baseballs into a few exhibition games.

    One of Finley's most memorable stunts occurred in the 1972 season, when he offered a cash reward to any of his players who could grow a mustache by Father's Day. One A's pitcher, Rollie Fingers, was up to the task and grew his trademark curly mustache that he maintains to this day.

    Because of this, Rollie Fingers' 1973 contract included a $300 bonus for growing a mustache and an extra $100 for the purchase of mustache wax.

6. Brad Lidge (Houston Astros)

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    After establishing himself as one of the best closers in the game in 2004 and 2005, Brad Lidge was a free agent after a shaky 2006 season.

    The Astros took a chance and re-signed Lidge to a one-year, $5.35-million contract, but they were sure to include a surefire way for Lidge to earn some extra cash.

    The Astros promised Lidge, a relief pitcher with seven career at-bats, a $25,000 bonus if he could manage to win the Silver Slugger Award, given annually to the best hitter at each position.

    Lidge didn't manage to win the Silver Slugger (he hasn't even registered an at-bat since 2004), and things didn't go any better for him on the mound. The pitcher struggled, he was demoted from the closer's role, and he was eventually traded to the Phillies in November 2007.

5. Alex Rodriguez (New York Yankees)

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    It's rare that a player can opt out of the final year of a $252 million contract because he thinks he can make more money. That's exactly what Alex Rodriguez did in 2007 after a career year, and the Yankees did everything they could to re-sign the superstar.

    The Yankees ended up signing A-Rod to a 10-year, $275-million contract that includes millions of dollars worth of incentives if Rodriguez is able to achieve certain career milestones. One clause in particular, however, seemed just a bit petty and unnecessary.

    Rodriguez had the option to void his contract with the Yankees after 2008 or 2009 unless the club increased his 2009-10 salary by $5 million per year or $1 million more than highest-paid MLB position player.

    A-Rod is often accused of being a selfish prima donna, and this clause certainly did not help his case. I guess having the distinction of being "the highest-paid player in baseball" holds almost as much clout as a World Series title.

4. Steve Young (Los Angeles Express)

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    The Los Angeles Express of the USFL had to pull out all of the stops to lure superstar BYU quarterback Steve Young away from the NFL in 1984. They managed to convince Young to sign a 10-year, $40 million contract to play in the USFL.

    They didn't have enough money at the time, however, so they promised to pay $34.5 million of the deal in the form of an annuity, where Young would receive increasing annual payments starting in 1990. Because of the nature of the annuity, Young will continue to get paid until 2027, when he will receive a check for nearly $3.2 million.

    To add insult to injury, Steve Young wasn't enough to draw sufficient interest to the USFL and the league folded in 1986.

3. Charlie Kerfeld (Houston Astros)

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    Charlie Kerfeld helped lead the Astros to the NLCS as a rookie pitcher in 1986. As you can see, he certainly knows how to celebrate.

    During the offseason, the Astros wanted to get another year out of the young pitcher who had gone 11-2 for them in the regular season and began negotiating one of the strangest contracts in sports history.

    Kerfeld asked for $110,037.37, matching his number 37 jersey, to pitch in 1987. On top of that, he received 37 boxes of orange Jell-O in the deal.

    Unfortunately, the Jell-O combined with the Busch proved to be a poor combination, as the pitcher battled weight problems and pitched less than 30 innings for the Astros in 1987 before being sent to the minors. 

2. Bobby Bonilla (New York Mets)

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    When you think of ridiculous contracts, this one has to take the cake. It was engineered by none other than former Baseball Tonight analyst Steve Phillips when he was GM of the Mets.

    The Mets wanted to sever ties with aging slugger Bobby Bonilla, but he was still owed $5.9-million on his contract.

    Rather than pay him the money, the Mets organized a deal where Bonilla would opt out of his contract and they would defer the payment until 2011...with interest.

    The deal allowed the Mets to free up some payroll and acquire players that would lead them to the World Series in 2000, but on July 1 of this year, Bonilla will start cashing in big time.

    Starting on July 1, 2011, Bobby Bonilla will remain on the Mets payroll for 25 years, collecting an annual salary of $1,193,248.20, a grand total of nearly $30-million.

    Bonilla, who hasn't played in the majors since 2001, will be 73 years old when his payments stop. 

1. Spencer Prior (Cardiff City)

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    This has to go down as the most ridiculous contract clause of all-time. And after what has already been on this list, that's saying something.

    In 2001, the Cardiff City F.C., the best-supported soccer team in Wales, signed defender Spencer Prior to a three-year contract worth 700,000 pounds (about $1.1 million). Nobody will ever know why the following clause was included in the contract by Cardiff City owner Sam Hammam.

    In order to sign the contract with Cardiff City, Prior had to agree to eat sheep's testicles and have "physical liaisons" with sheep.

    While the "liaisons" were dismissed as a joke about Welshmen, Prior actually did have to eat sheep's testicles. Apparently, it was a tradition for players on the team and was thought to bring them good luck. I refer you to the words of Cardiff City manager Alan Cork:

    "There are two types of balls at this club: footballs and sheep’s balls."

    Prior agreed to eat the testicles, as long as they were cooked with lemon, salt and parsley.

    *Just so you know I'm not making this up...here is the article from the Manchester Evening News.

    Follow me on Twitter @CWardHenninger