50 Bitter Contract Holdouts That Rocked Pro Sports

Darren - April 28, 2022

50 Bitter Contract Holdouts That Rocked Pro Sports

Darren - April 28, 2022

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