Sports

50 Bitter Contract Holdouts That Rocked Pro Sports

Darren - April 28, 2022

Sports

50 Bitter Contract Holdouts That Rocked Pro Sports

Darren - April 28, 2022

44. Jorge Masvidal

Masvidal became a global superstar in 2019 after he knocked out Ben Askren. His flying knee caused the quickest KO in UFC history. Meanwhile, Masvidal’s persona and image helped him to capture the love of fans. Even though he never won a title he was one of the company’s biggest draws. This was more important than winning fights because it brought money to the promotion.

But Masvidal wanted to see more zeros at the end of his paycheck. He demanded more from the notoriously tight-fisted UFC. They reacted in stubborn defiance but in the end, he got what he wanted. After begging the UFC to release him, he ended up with the contract he wanted. Somehow, he received the third-biggest deal in the promotion’s history (via Marca).

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43. T.J. Watt

Watt is one of the top defensive players in recent NFL history. If it wasn’t for Aaron Donald, Watt would be out on his own. He turns the Pittsburgh Steelers into a different beast when he’s on the field. But like all of the best players, he expected his franchise to pay him well. Usually, contract holdouts arise when there is a dispute between both parties.

The linebacker engaged in a soft holdout where he attended preseason practices. But he only participated in individual routines and did his work. In the end, Pittsburgh realized that it was stupid to risk losing him. They handed him a massive $112 million contract with a massive signing bonus (via USA Today Sports). They knew their fans would revolt if they let him go.

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42. Tyson Fury

Fury is arguably the greatest heavyweight boxer of the modern era. He disappointed fans when he refused to face his British rival, Anthony Joshua in 2021. It appeared as though they agreed on a deal to fight but it never materialized. One of the main reasons was that Fury refused to sign the contract. He wanted Joshua’s team to secure a bank guarantee that the money was available (via Mirror).

This never arrived so Fury walked away from the negotiating table. This was a potential $250 million mega-fight but Fury didn’t care. Boxing contract holdouts aren’t like other sports because the athletes have more control over their destinies. In the end, fans suffered because they didn’t get to see one of the biggest potential fights ever. It’s a shame but that’s the nature of boxing.

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41. Tom Brady

Technically this wasn’t a contract holdout in the traditional sense, but it was a massive story. Brady was synonymous with the Patriots for two decades. But he maintained a tense working relationship with head coach Bill Belichick. The pair treated each other with cold professionalism but didn’t have a close bond. Then Brady rocked the world when he refused to sign a new deal.

Instead, he opted to become a free agent and pursue a fresh start. It was a shock because nobody expected him to leave the Patriots after so long. Finally, he joined the Buccaneers and won another Super Bowl. It was a massive moment for his career because he broke many records and made a lot of money. Brady proved that he could do it without his former coach too (via AS).

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40. Cris Cyborg

Few women incite as much fear as Cyborg. The Brazilian MMA fighter is one of the most dominant female athletes ever. Her imposing physique and ferocious skills made her a ruthless opponent. In 2o18, she lost a title fight against Amanda Nunes after her fellow Brazilian knocked her out. It was a changing of the guard moment but fans wanted to see the rematch (via MMA Fighting).

However, they never got it because Cyborg left the UFC. The promotion failed to build a featherweight division around her during her tenure as champion. She also had a poor working relationship with UFC president Dana White. In the end, she decided to test the waters and make as much money as possible. Cyborg signed a new deal with Bellator and killed off hopes of a Nunes rematch.

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39. Chandler Jones

Jones had a productive six years with the Arizona Cardinals. But a dispute in 2022 resulted in one of the franchise’s most notable contract holdouts. In short, Jones wanted more money but the Cardinals didn’t want to pay him. It’s a story as old as time and it ended with the player departing for pastures new. Arizona felt conscious about their salary cap and didn’t want to blow it on the veteran pass-rusher.

The Cardinals opted to move him on after signing J.J. Watt and DeAndre Hopkins to big contracts. Las Vegas picked up Jones on a three-year deal worth $51 million. It was a massive amount of money and it’s clear why Arizona didn’t want to commit. But Jones got his way in the end and moved to a new city. He didn’t complain about leaving Phoenix for the city of sin (via Bleacher Report).

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38. Steve Larmar

On the face of it, Larmar’s situation wasn’t out of the ordinary. There were many contract holdouts in the nineties and he wanted more money. Many stars earned millions of dollars but he didn’t crack seven figures. Furthermore, he was tired of life in Chicago and wanted a fresh start. But he had a phenomenal record of never missing an NHL game in his career.

Larmar went 884 games in a row before he failed to appear on the ice. It’s a shame because he never allowed injuries to stop him. In the end, it was money that prevented him from breaking the overall record. However, it ended well for him because he wound up with the Rangers. That’s where he won the Stanley Cup for the first time so he made the right choice (via Fansided).

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37. Terence Crawford

Crawford is one of the top boxers of his generation and a former pound-for-pound king. However, he suffered because his promoter Top Rank made life difficult for him. They affected his legacy because they refused to sanction a clash with his rival, Errol Spence Jr. Crawford refused to sign a new deal with the promotion but things became even more twisted.

Next Crawford sued them after accusing Bob Arum of racial bias. It was an extremely messy scenario that tarnished the sport of boxing. But Crawford felt justified because he alleged that they failed to represent him properly. It also brought the boxing promoters into focus because athletes realized that they had more power. Crawford sought over $10,0000000 in compensation (via Boxing Scene).

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36. Steven Gerrard

Gerrard is one of Liverpool’s greatest-ever players. The midfielder came through the academy and became the first team’s captain. He provided a stream of iconic moments for the club. But he also attracted the eyes of other teams because of his brilliance. Meanwhile, Liverpool didn’t have the roster to compete with the best in the league. Nor did they have as much money.

In 2005, fans burned Gerrard’s shirt because they thought he was going to join Chelsea. Jose Mourinho made no secret of the fact that he wanted the Liverpool star. In the end, after one of the most dramatic contract holdouts in Premier League history, he signed a new deal. Gerrard never played for another English club but joined the L.A. Galaxy at the tail-end of his career (via TalkSport).

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35. Jamal Adams

In 2020, Adams had a major dispute with the New York Jets. He wanted more money and he didn’t think that the franchise appreciated him. One of the nastiest contract holdouts of the year ensued and they traded him to the Seahawks. Seattle desperately wanted to recreate the Legion of Boom and thought that he was a good fit. They made him the highest-paid safety in the NFL.

Meanwhile, the Jets received multiple draft picks from Seattle. This pleased them because it enabled them to rebuild their team over the next few years. Adams earned a fortune but the Seahawks didn’t emerge as winners. That’s because he missed many games and failed to make an impact when he appeared. It proved that the Jets made the right call (via USA Today).

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34. Kayla Harrison

Harrison was an Olympic judoka who unleashed carnage upon her opponents. Then she moved to MMA and took her violence to the next level. She became an elite fighter with the PFL and won millions of dollars. However, she came to the end of her deal with the promotion. This created one of the most interesting contract holdouts in the sport (via Marca).

Suitors included the UFC and Bellator because they had big opponents for her. The likes of Amanda Nunes and Cris Cyborg made sense as match-ups. Fans hoped she’d move because she reached her ceiling with the PFL. But there was a major anticlimax when she inked a new contract. It’s good for her because she makes lots of money and that’s what fighting is about.

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33. Mark Messier

Messier had an excellent career but he was no stranger to NHL contract holdouts. In 1991, he had his first massive spat with the Edmonton Oilers. Two years remained on his deal but he refused to play unless they gave him a lucrative payrise. Instead, the Oilers offloaded him to the Rangers in a major trade. Messier won a Stanley Cup with the franchise and had a great time.

Then he incited the wrath of fans by demanding that the franchise double his salary. It apepared as though they were ready to show him the door. But this time he got what he wanted after he sat out until January. They handed him a new deal and he got on with his career. Players gamble in this position because it depends on their value to the team (via Grantland).

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32. Kylian Mbappe

Mbappe is one of the most exciting young players on the planet. PSG spent a fortune when they bought him Monaco. He helped transform them into a European powerhouse and won the World Cup with France. However, he refused to extend his time in Paris. This worried his club because they spend over a hundred million dollars. Meanwhile, his image was worth an incalculable amount of money.

Real Madrid kept a keen eye on the situation because they wanted to lure him to Spain. Finally, in 2022 it appeared as though they secured his services. Despite PSG desperately offering record figures to keep him, Mbappe wanted to leave. Even more dramatically, he left as a free agent so the team wouldn’t earn a single cent. It’s a massive blow for the oil-rich club (via Daily Mail).

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31. B.J. Penn

It’s never a good look when a champion leaves a fight promotion. That’s because they can’t claim to have the best athlete in the world anymore. However, the UFC found themselves in this situation with Penn after he defeated Matt Hughes. It was a major shock when he submitted the former champion. But an even bigger one when he signed with K-1 to kickbox in Japan.

Then the UFC immediately stripped him because they said that it was the same as vacating his title. Penn sued the promotion because he cited the Ali act. In the end, he fought several times in Japan before returning to the UFC. It was one of the most dramatic contract holdouts in MMA history. Penn’s legacy also impacted other fighters becuase it set a precedent for the UFC (via Sherdog).

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30. Chris Johnson

A player must perform well until they secure the biggest contract of their life. Luckily, that was the case for Johnson. He was brilliant for the Titans before 2011. Then he wanted more money and had a dispute with the front office. The big question was who would blink first? In the end, Tennessee backed down after he made it clear he was ready to sit out.

They handed him a massive contract worth over $50 million. But the problem was that he never justified the terms of that deal. Johnson’s productivity went into severe decline and the Titans came off as losers. That’s always the risk in football and it’s the reason why teams resist overpaying their stars. Sometimes the gamble pays off but not in Johnson’s case (via Athlon Sports).

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29. A.J. Brown

The Jaguars overpaid their wide receiver, Christian Kirk, in 2022. Then a bunch of other wideouts sat up because they realized they could force their teams to give them more money. Nobody can blame athletes for trying to maximize their value because sporting careers are very short. However, Twitter didn’t react kindly to Brown when he sat out of the Titans’ offseason activities.

They issued death threats and called him a bad teammate. Brown was just one of several stars involved in contract holdouts but they didn’t care. Of course, this didn’t encourage him to stick with the franchise either. Why should he show loyalty to a team when the fans openly hate him? Brown knows that a single injury could damage his career earnings so he must milk it (via NBC Sports).

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28. Juwan Howard

Howard knew his value before the 1994 NBA Draft. That’s why he held the Wizards to ransom. He was a member of Michigan’s iconic ‘Fab Five’ and attracted national attention before he even played in the NBA. They never won an NCAA title but they were a brilliant team. That’s why Howard held out and demanded that Washington pay him massive money.

The franchise bowed down and gave him a huge rookie contract. Then, they renegotiated and made him the first $100 million player in NBA history. That’s right, he secured that deal before Michael Jordan. Howard was the only Fab Five member to win an NBA Championship. He secured two rings during his time in the league. Now he’s a highly-rated coach (via Sportscasting).

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27. Nate Diaz

Diaz is one of the UFC’s biggest stars. The Stockton native handed Conor McGregor his first defeat in the promotion. However, he has maintained a tense relationship with the promotion. He reached the final fight of his deal but the UFC refused to hand him an easy match-up. First, they tried to feed him to rising prospect Khamzat Chimaev to increase his profile.

They didn’t want Diaz to maximize his earning power by winning in his final fight. This impasse rumbled on and on, frustrating Diaz and his team. It remains to be seen what happens next for the Californian. But it’s a shame that he’s on the shelf like this. Fans want to see great fighters in action but money makes the world go around. The UFC is conscious of this (via SB Nation).

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26. Sean Gilbert

Bizarrely, Gilbert is the uncle of Darrelle Revis, who also features on this list. Maybe he influenced his nephew because Gilbert had no hesitation in doing the right thing for his career. The Redskins slapped him with the franchise tag in 1997. This infuriated him because he wanted to maximize his earnings and that wasn’t possible. That’s why he sat out for the season.

In 1998, Washington admitted defeat and traded him to Carolina. But the problem was that Gilbert’s career went into decline. He made his money so it was a success from that standpoint. It’s just a shame that he lost a year of his prime because the Redskins didn’t want to meet his value. The Panthers would argue he wasn’t worth it anyway because of his performances (via Fansided).

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25. Emmitt Smith

Sometimes a player is conspicuous because they aren’t on the field. Smith proved this point because he refused to perform his duties for the Cowboys at the start of the 1993 season. The running back was one of the team’s most dangerous attacking threats but Jerry Jones didn’t want to pay him. This created tension between the player and the owner (via NBC Sports).

Smith wanted quarterback money but Jones refused to sanction that. He missed the entire summer program before skipping the first two games of the season. Finally, both parties reached a compromise. Smith became the highest-paid running back of all time but he didn’t get the QB deal he desired. In the end, it’s probably what he deserved based on the market.

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24. Darelle Revis

Revis was one of the Jets’ best players in 2010 but he drove his new head coach crazy. He engaged in one of the most dramatic contract holdouts of the decade because Woody Johnson wouldn’t pay him. Revis shrugged his shoulders and was happy to sit out. The new season edged closer but Revis didn’t care and missed the offseason training schedule.

In the end, Ryan forced the issue because he didn’t want to lose the cornerback. He even drove to Johnson’s house because he wanted to make it clear that this was a massive deal. Finally, they made the new contract happen and Revis signed up. They even made it to the AFC title game that season. It’s safe to say that the extension was a success because Revis was brilliant.

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23. William Gallas

In 2010, Arsenal offered Gallas a two-year extension to his deal. However, the French international snubbed their deal because they didn’t offer him a wage increase. This shocked the club because they broke their standard one-deal extension policy for over-30 players. Gallas didn’t appreciate this and rejected it. Eventually, he departed and joined their rivals, the Spurs.

This was remarkable because these teams are intense rivals. Meanwhile, Gallas was the club captain at the time. After one of the team’s biggest contract holdouts, he left under a cloud. Gallas broke all of the bridges with the club and the fans hated him. It didn’t matter that he served them faithfully before this. He broke an unwritten rule that no player should ever do (via The Mirror).

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22. Le’Veon Bell

Bell was a moron with a lot of talent. He tried to hold the Steelers to ransom in 2018 but it turned out badly for him. He didn’t count on James Conner stepping up and performing well for the franchise. In the end, Pittsburgh shrugged its collective shoulders and allowed him to sit out. Bell missed an entire year of football in his prime because he overvalued himself (via Bleacher Report).

Finally, he escaped to the New York Jets. But that was like leaving Purgatory and stepping into Hell. He was appalling for Gang Green and hated the coaching staff. Somehow he ended up playing for the Chiefs but couldn’t earn a starting place. Bell was excellent for Pittsburgh before it all went wrong. He counted his chickens before they hatched and lost almost $900,000 a week in the process.

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21. John Hannah

There’s nothing new about contract holdouts. The only difference is how widely the media reports them. In 1977, Hannah was one of the Patriots’ most important offensive linesmen. After a distinguished career, he was voted into the Hall of Fame. But it wasn’t always sunshine and roses for the player and the franchise. That season, he sat out for three games because of a dispute.

Eventually, New England acknowledged his value and offered him a lucrative extension. Hannah settled down and nothing more was said about it. He repaid the contract in style as he spent eight more seasons with the team. He even helped them to a Super Bowl appearance. Hannah was one of the best players of his generation and the franchise knew it (via UPI).

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20. Kam Chancellor

Chancellor’s situation proved that contract holdouts don’t always work in favor of the player. Remember, they stand to lose a lot of money if the franchise doesn’t blink. Some athletes can handle this because they know they’ll make it back quickly. But others aren’t in a financial position to absorb that loss. Chancellor found this out in 2014 because he didn’t get his way.

Seattle refused to restructure or offer him more money when he requested it. They were already in a tricky situation because they restructured Marshawn Lynch’s contract. Chancellor wasn’t in a position to bargain. Finally, after he missed the first two games of the season he came back. But he didn’t gain anything that he wanted – officially at least (via Washington Informer).

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19. Jon Jones

The UFC has a history of contract holdouts because they grossly underpay their fighters. Jones was one of their biggest stars but came with a lot of baggage. After vacating the 205 lb. title, he announced his move up to heavyweight. Fans hoped for a super fight between Jones and Francis Ngannou but the UFC disappointed them. They refused to meet Jones’s demands so he sat out.

There are two sides to this story. First, the UFC is infamously cheap and refuses to make their best athletes into big stars. They want brand ambassadors instead of global icons. Meanwhile, Jones is a problematic individual. His doping record and legal issues damage his leverage. It’s difficult to see him winning this war of numbers with the promotion (via SportsJoe).

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18. Phillipe Coutinho

Coutinho was one of Liverpool’s best players before he departed for Barcelona. The diminutive Brazilian combined sublime trickery with spectacular goals. This made him a massive fan favorite at Anfield but things ended badly. He left under a cloud after he forced an exit (via Four Four Two).

When the Catalan giants came in it, it turned Coutinho’s head. He wanted his dream to move to Spain but Liverpool resisted. They refused to sell unless Barcelona made a ridiculous offer. In the end, that’s what happened. After one of the biggest contract holdouts of 2018, Coutinho made his move. Liverpool reinvested the money and won the league.

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17. Eric Dickerson

Dickerson was brilliant for the Rams when they were at their peak. But the pair had a painful parting of the ways. His financial issues dragged on through several seasons. In 1985, he had one of the most dramatic contract holdouts of the year. He sat out for two games before they lured him back to action. This came after a record-breaking year in 1984.

In 1987, Dickerson’s problems came to a head again. This time there was no solution except for trade. The Rams sent him to Indianapolis after an impasse. It was a shame because Dickerson was brilliant for the team. The Colts didn’t see the best of him but at least he repaired his relationship with the Rams. They retired his jersey when he officially stepped away from the sport.

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16. Ken Dryden

Dryden had a magnificent career with the Montreal Canadiens. However, the reality is that it wasn’t always smooth sailing between the player and the franchise. They had one of hockey’s biggest contract holdouts. The goaltender wanted the team to pay him after he won a pair of Stanley Cups. On an individual basis, he also claimed the Conn Smythe Trophy.

But the Canadiens refused to meet his self-proclaimed value. Dryden didn’t back down and sat out for the entire 1973 season. Finally, he returned and the team paid him his dues. But it’s a shame that they couldn’t reach an agreement before this because the fans lost out. Money is one of the biggest dividers in the world of sports as proved in this case (via N.Y. Times).

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15. Al Iaquinta

Iaquinta fought in the UFC lightweight division for many years. The straight-talking New Yorker famously took on Khabib Nurmagamedov at short notice. He didn’t win that title fight but he earned admirers because he took the champion to a decision. However, Iaquinta had problems with the promotion because they underpaid him. He’s one of many fighters who had contract holdouts (via The Score).

In 2016, he withdrew from UFC 205 because the promotion didn’t pay him enough. Iaquinta claimed that the cost of injuries and a training camp didn’t justify fighting. He returned to action but was away from the cage for over a year. It’s a shame but it’s a reality that the UFC underpays its fighters compared to other sports. Iaquinta did the right thing for his career.

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14. Kelly Stouffer

There was nothing remarkable about Stouffer’s playing career except for one detail. He forced the Seahawks to pay him a fortune because he refused to play. . They made him the sixth overall pick in 1988 after his impressive displays at Colorado State. However, their contract package didn’t please Stouffer and he refused to back down. He sat out for the full season (via The Coloradoan).

In the end, the Seahawks backed down and overpaid the quarterback. He never amounted to much in the NFL but it didn’t matter because he made his money. The outcome of this deal changed the dynamic between rookies and teams. It even impacted the likes of the Raiders and JaMarcus Russell. These days it’s harder for players to hold out against teams.

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13. John Riggins

In 1980, Riggins rocked the Redskins when he dramatically retired. He attempted to restructure his lucrative contract with the franchise but Washington rejected this. Then the running back quit the sport because he fell out of love with it. He sat out for an entire season before Joe Gibbs knocked on his door. The new head coach attempted to lure him back to football because he wanted his trade value.

Riggins agreed to play but only if the Redskins inserted a no-trade clause. However, this was a blessing in disguise for Gibbs because he helped the franchise to an unprecedented period of success. Riggins helped the franchise to three Super Bowls during his second tenure with the team. Meanwhile, his mind was in a better place and he was making more money than before (via Washington Post).

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12. Diego Costa

Costa was a defender’s nightmare because of his tenacity and penchant for the dark arts. He starred for Chelsea in the Premier League after he left Atletico Madrid. But he went AWOL after a massive fallout with the manager, Antonio Conte. Then he demanded a transfer but the team refused to sanction it. Costa traveled home to his native Brazil and refused to play for the Londoners.

Chelsea demanded that he return and fulfill the terms of his contract but Costa rejected them. In an explosive interview with Sky Sports, he told them that Chelsea treated him like a ‘criminal.’ Costa claimed that he was on the brink of renewing his contract before the coach intervened. In the end, he left the club and returned to Madrid. It was a grim time for both parties.

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11. Joe DiMaggio

MLB stars rarely engage in contract holdouts because they receive guaranteed contracts. That’s also why great players stay with bad teams because they’re making money. However, DiMaggio famously had a financial spat with the Yankees. He demanded a $40,000 salary but the franchise wasn’t willing to sanction that. They ended up at loggerheads with each other.

DiMaggio overestimated his star power because the Yankees didn’t back down. In the end, they gave him a $25,000 deal. This was much lower than the amount that he demanded. However, if he didn’t play the team wouldn’t pay him so he was in a no-win situation. Sometimes front offices hold all of the cards and the player must bend the knee (via PBS).

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10. Glenn Robinson

Robinson had a stellar college career at Purdue and entered the NBA Draft in 1994. His contract negotiations with the Bucks are the stuff of legend. That’s because he demanded an outrageous sum of money from the team. The franchise resisted but in the end, they agreed to give the rookie a ludicrous $100 million deal. It’s impossible in the modern day but the 1990s were a wild time.

Furthermore, they guaranteed every dime of the contract. Robinson was the winner because he wasn’t a $100 million player at the time. He became a two-time All-Star but he had a reasonably average career. Finally, he won a Finals ring when he moved to the Spurs in his last season as a professional. He achieved a lot and made a fortune (via Chicago Tribune).

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9. Deebo Samuel

Samuel was the 49ers’ most effective player in 2021. He demanded a trade after San Francisco refused to meet his demands of how he was being used. It was one of the most shocking holdouts of the year because he came off a great year. It appeared as though the wideout and the franchise were a match made in heaven. But that’s not the case and he wanted to leave (via KNBR).

The Jets were a franchise with a serious interest in him. They were ready to offer a first-round pick as well as multiple others in exchange for the star. However, it’s not that simple because the Niners didn’t have pressure to trade. Meanwhile, every day Samuel misses training will cost him $40,000. Even if he sits out, he may not become a free agent because of the lack of accrued playing time.

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8. Francis Ngannou

Ngannou is one of the most ferocious fighters on the planet. The giant Cameroonian possesses frightening knockout power. This helped him win the UFC heavyweight championship. He should be a promoter’s dream but that’s not how it turned out. The UFC refused to match his financial demands and one of the most bitter contract holdouts ever emerged.

They made him an offer and told him that if he didn’t like it, he could walk. Ngannou and his representative shrugged before nodding their assent. This left the UFC in an embarrassing situation because he flirted with boxing. He made the promotion appear to be cheap because they wouldn’t pay their star. Ngannou may be the winner at the end of all this (via Give Me Sport).

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7. Bo Jackson

Jackson was a young man of extreme principle. When the Buccaneers tricked him into missing his final season of college baseball eligibility, he said he’d never play for the franchise. Then Tampa Bay picked him in the first round of the NFL Draft. However, Jackson stunned them by declaring for the MLB Draft. He spent three seasons with the Kansas City Royals and became an All-Star.

Then, Al Davis lured him back to football with the Los Angeles Raiders. Jackson duly agreed and signed an NFL contract with the franchise. It was a massive demonstration of player power because he refused to allow the Bucs to bully him. They stood back in sullen silence as he showed his skills in the league. Jackson also became the first player to achieve NFL and MLB All-Star status (via Tampa Bay Times).

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6. Pierre-Emerick Aubemeyang

The soccer world thought that Arsenal pulled off a coup when they signed Aubemyang. The Gabonese striker proved that he was one of the best forwards in the world. However, he tired of being their focal point because the club showed few signs of progression. This put him at odds with the team’s manager, Mikel Arteta. Furthermore, Aubemeyang wanted more money.

Arsenal didn’t want to match his demands because of his age and their wage structure. After one of the most intense contract holdouts in recent memory, they sent him to Barcelona. Almost immediately, he became one of the Catalan giant’s biggest stars. He also made more money in Spain than in London. It’s safe to say that he was the winner because he achieved everything he wanted (via The Mirror).

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5. Alexei Yashin

Yashin had a great career with the Ottawa Senators before his relationship with the franchise collapsed. He believed that his contract allowed him to void the final year and become a free agent. However, the Senators disputed this and refused to release him. This created an impasse between the player and the franchise. But it continued to escalate (via The Globe And Mail).

The Russian sat out for the entire 1999-2000 season because he thought this would guarantee free agency. But Ottawa brought him to court and claimed he failed to meet the terms of his contract. The court of arbitration agreed and Yashin found himself back on the ice with the Senators. The fans didn’t give him a warm welcome but he had a decent final year in Canada.

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4. Harry Kane

Daniel Levy is one of the toughest negotiators in the world of soccer. The Spurs chairman refuses to allow players to leave for a dime under their value. Meanwhile, Kane was the team’s star player in 2021. But he was tired of carrying them on his shoulders and wanted to leave. Manchester City made their interest known and turned his head even further.

But Levy wanted outrageous money for the England captain. Kane made no secret of the fact that he wanted to leave. He said that he made a gentleman’s agreement with Levy before the season. But money is more important than honor in the modern world. In the end, City couldn’t afford Spurs’ valuation and Kane stayed. The team declined even further in 2022 (via Sportsmole).

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3. Conor McGregor

Irish MMA superstar McGregor had a meteoric rise to fame. However, his relationship with the UFC has had its ups and downs. One of the biggest came before UFC 200. First, the promotion booked McGregor to fight Nate Diaz in a rematch. But then he had a major dispute. He refused to engage in media duties because he wanted to focus on his preparation.

Then he pretended to retire as he played hardball with the promotion. Nonetheless, the UFC refused to back down. They pulled him from the fight and replaced him with Brock Lesnar. In the end, McGregor sat out for a few months after one of MMA’s biggest contract holdouts. He returned to action and defeated Diaz in a rematch (via FOX Sports).

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2. Ben Simmons

Australian basketball star Simmons is one of the most infamous athletes in recent years. The NBA rarely experiences contract holdouts but Simmons brought it to the next level. He refused to play for the 76ers in 2021 because of mental health issues. In the end, the franchise fined him around $10 million throughout the season.

This frustrated his team and his coaches. Furthermore, Philadelphia is one of the most hostile sports cities in the world. It’s not the best place for fans to hate an athlete. But Simmons didn’t care and forced an exit. Finally, he achieved his wish and moved to the Brooklyn Nets. Simmons also attracted heat in 2022 after missing key playoff games (via CBS Sports).

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1. Aaron Rodgers

Everybody knows Rodgers because he is one of the greatest quarterbacks of all time. The Packers star spent his entire career with the franchise and won a Super Bowl. He was also a two-time NFL MVP award winner. However, in 2020, he rocked the world with one of the most dramatic contract holdouts ever. He refused to train because he wanted to leave Wisconsin.

Then he failed to show up for preseason practice. Finally, the Packers agreed to negotiate his deal for a final season. Fans and analysts widely expected that the Broncos would trade for him in 2021. But that’s not what happened. In the end, Rodgers signed a new contract with the Packers and became even wealthier. It also put the highly-rated Jordan Love in a very strange position (via NBC Sports).

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50 Bitter Contract Holdouts That Rocked Pro Sports

50 Bitter Contract Holdouts That Rocked Pro Sports

44. Jorge Masvidal

43. T.J. Watt

42. Tyson Fury

41. Tom Brady

40. Cris Cyborg

39. Chandler Jones

38. Steve Larmar

37. Terence Crawford

36. Steven Gerrard

35. Jamal Adams

34. Kayla Harrison

33. Mark Messier

32. Kylian Mbappe

31. B.J. Penn

30. Chris Johnson

29. A.J. Brown

28. Juwan Howard

27. Nate Diaz

26. Sean Gilbert

25. Emmitt Smith

24. Darelle Revis

23. William Gallas

22. Le’Veon Bell

21. John Hannah

20. Kam Chancellor

19. Jon Jones

18. Phillipe Coutinho

17. Eric Dickerson

16. Ken Dryden

15. Al Iaquinta

14. Kelly Stouffer

13. John Riggins

12. Diego Costa

11. Joe DiMaggio

10. Glenn Robinson

9. Deebo Samuel

8. Francis Ngannou

7. Bo Jackson

6. Pierre-Emerick Aubemeyang

5. Alexei Yashin

4. Harry Kane

3. Conor McGregor

2. Ben Simmons

1. Aaron Rodgers

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