My Way or the Highway? 10 Epic Sports Contract Standoffs

Athletes often negotiate hard to secure more money or include better terms in their contracts.

PUBLISHED NOV 13, 2023

Image Source: Pio Esposito and Lorenzo Pirola of Italy clash with Nicko Sensoli of San Marino during the UEFA U21 Euro 2025 Qualifier between San Marino and Italy at San Marino Stadium / Jonathan Moscrop/Getty Images

Epic Sports Contract Standoffs

Image Source: Lighthouse Source/Getty Images

In the world of pro sports, where the money is big and the stakes are high, contract holdouts often steal the spotlight. Athletes often negotiate hard to secure more money or include better terms in their contracts. But who actually wins these high-stakes battles? From the adrenaline-pumping battles of football to the strategic maneuvering in baseball, here are the superstar athletes, clever negotiators and the teams they went up against.

1. Juwan Howard

Image Source: — Head Basketball Coach Juwan Howard of the Michigan Wolverines. Aaron J. Thornton/Getty Images)

Juwan Howard's rise from the "Fab Five" program at Michigan gave him the superstar status even before the 1994 NBA draft. Rather than settling for a typical rookie contract, Howard held out for a substantial payout, securing an impressive 11-year, $36 million deal with an option to opt-out after two seasons. This initial financial success was just the beginning. Howard eventually left that contract and signed a massive $100 million deal, becoming the first player in NBA history to reach such a milestone. In both the short and long term, Juwan Howard and his agent unquestionably emerged as the winners.

2. Alexei Yashin

Image Source: Ottawa Senators alumni Alexei Yashin #19 turns to skate up ice during the 2017 Scotiabank NHL100 Classic Ottawa Senators Alumni Game / Andre Ringuette/NHLI via Getty Images — Ottawa Senators alumni Alexei Yashin #19 turns to skate up ice during the 2017 Scotiabank NHL100 Classic Ottawa Senators Alumni Game / Andre Ringuette/NHLI via Getty Images

Alexei Yashin tried to break his contract but faced consequences. As Ottawa Senators captain, he wanted out before the 1999-2000 season and sought to void the final year of his contract for free agency. The Senators resisted. This sparked a battle between Yashin and the Senators. Yashin held out, hoping to become a free agent after a full season's absence. However, the Senators argued he owed them another year of service. So, he played for them in the 2000-01 season before being traded. Yashin later secured a lucrative deal with the New York Islanders.

3. Kam Chancellor

Image Source: Injured Seattle Seahawks Safety Kam Chancellor before the NFL game between the Seattle Seahawks and the San Francisco 49ers / Cody Glenn/Icon Sportswire via Getty Images — Injured Seattle Seahawks Safety Kam Chancellor before the NFL game between the Seattle Seahawks and the San Francisco 49ers / Cody Glenn/Icon Sportswire via Getty Images

Kam Chancellor, a key member of the Seattle Seahawks' "Legion of Boom" defense, along with Earl Thomas and Richard Sherman helped the team win a Super Bowl a couple of seasons ago. Chancellor wanted to secure a more lucrative deal like Sherman and Thomas. His holdout ended two weeks into the NFL season, and he returned without any additional money or a complete contract overhaul. Andrew Brandt of the MMQB provided an alternative perspective, suggesting that while it may seem the Chancellor "caved" on the surface, it's crucial to consider the forgiveness of fines and how the contract situation will eventually be resolved. At present, it's uncertain who the clear winner is in this situation.

4. Ken Dryden

Image Source: Former Montreal Canadien Ken Dryden skates during the Centennial Celebration ceremonies prior to the NHL game between the Montreal Canadiens and Boston Bruins on December 4, 2009 at the Bell Centre in Montreal, Quebec, Canada. / Richard Wolowicz/Getty Images — Former Montreal Canadien Ken Dryden skates during the Centennial Celebration / Richard Wolowicz/Getty Images

The Montreal Canadiens' rich history of success owes much to numerous players and coaches, and among them, goalie Ken Dryden stands as a true legend. Dryden was a formidable presence, unflinchingly stopping pucks with fearless determination. He embodied the Canadiens' winning spirit. Before his famous holdout in 1973, Dryden had already earned a Conn Smythe Trophy and two Stanley Cups. He was at the pinnacle of his career and wanted the compensation he deserved. However, the Canadiens stood their ground, leading Dryden to sit out the entire 1973-74 season. Eventually, he returned to his championship-winning form, secured a deserved contract, and raised Lord Stanley's Cup four more times.

5. Sean Gilbert

Sean Gilbert has a notable connection to this list – he's not only a holdout case but also the uncle of New York Jets cornerback Darrelle Revis, as reported by Mike Tanier in the New York Times. In 1997, Washington used the frustrating franchise tag on Gilbert. Unwilling to play under those terms, he chose to skip the entire season. By 1998, Washington's management grew frustrated and traded Gilbert to the Carolina Panthers. There, he signed a substantial $46.5 million contract. While he gained financially from the situation, his playing career in Carolina wasn't as successful, with five seasons, 15.5 sacks, and 140 tackles, falling well short of justifying the $46.5 million contract.

6. Don Drysdale and Sandy Koufax

One of the earliest instances of a holdout in baseball history involved two Hall of Fame pitchers, Don Drysdale and Sandy Koufax, who were teammates on the Los Angeles Dodgers in 1966. Despite being at the pinnacle of their careers, they sought an increase in their earnings.This holdout was not extravagant, as neither Drysdale nor Koufax missed any games. However, their refusal to take the field signaled an early indication of how athletes would approach contract negotiations in the future.

7. Chris Johnson

Image Source: Grant Halverson/Getty Images

Do you remember when Chris Johnson was the top pick in fantasy football drafts? The former 2,000-yard rusher was relishing a successful run with the Tennessee Titans. However, in preparation for the 2011 season, Johnson wanted a fatter paycheck. His holdout persisted until September 1, as reported by SI.com. That's when the Titans offered Johnson a four-year deal worth $53.5 million, to keep him with the team until 2016. But things didn't go as planned. Johnson continued to play in Tennessee until 2013, with his average yards per carry dropping to 4.1 during that period. His production declined while his earnings increased, typically an unfavorable outcome for the front office. In this case, the winner was Chris Johnson.

8. Pavel Bure

Image Source: Pavel Bure #10 of Russia during final match of League of Legends of World Hockey between Russia and Czech Republic at VTB / Oleg Nikishin/Epsilon/Getty Images — Pavel Bure #10 of Russia during the final match of League of Legends of World Hockey between Russia and the Czech Republic at VTB / Oleg Nikishin/Epsilon/Getty Images

Pavel Bure's contract dispute in 1998 resulted in him parting ways with the Vancouver Canucks. The tension and strained relationship between Bure and the Canucks organization was well-documented, as detailed by Tony Gallagher of the Province. Bure's frustration was palpable, and any hopes of reconciliation had faded. Consequently, he was traded to the Florida Panthers. Selecting a clear winner in this scenario is not straightforward. Bure was traded for the talented Ed Jovanovski, but the Panthers gained a prolific goal scorer while the Canucks acquired a centerpiece player who wasn't a distraction. In that sense, Bure didn't come out on top, making the Vancouver Canucks the winners.

9. JaMarcus Russell

Image Source: JaMarcus Russell looks to pass during the SEC Championship game between the Georgia Bulldogs and the LSU Tigers at the Georgia Dome in Atlanta/Mike Zarrilli/Getty Images — JaMarcus Russell looks to pass during the SEC Championship game between the Georgia Bulldogs and the LSU Tigers at the Georgia Dome in Atlanta/Mike Zarrilli/Getty Images

JaMarcus Russell's NFL career is one of the biggest busts in league history. Despite his shortcomings, he managed to secure a significant amount of money before ever playing an NFL down. After a prolonged holdout, Russell, the No. 1 pick in the 2007 NFL draft, signed a whopping six-year, $68 million contract. This massive payout raised eyebrows given his lack of NFL experience. Len Pasquarelli, writing for ESPN at the time, noted, "In terms of top overall picks, no one has held out longer than Russell since tailback Bo Jackson declined to sign with Tampa Bay altogether in 1986." While Russell's career quickly unraveled, his financial gains from this holdout situation were substantial. In the context of holdouts and financial success, JaMarcus Russell is an unexpected winner.

10. Eric Dickerson

Eric Dickerson, the NFL Hall of Famer, faced two contract holdouts during his illustrious career. In 1985, after his record-setting 2,105-yard rushing season, he held out for the Los Angeles Rams until they met his financial demands. The Rams gave in after he missed the first two games of the season. Five years later, he repeated the feat with the Indianapolis Colts, again successfully securing a significant sum of money. In terms of financial success through holdouts, Eric Dickerson emerged as a champion and set a standard for future NFL players. In that respect, he can be considered a winner.