The 25 Worst $100 Million Contracts in Sports History

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Team: Indiana Pacers

Contract value: Seven years, $126.6 million

Years: 2003-2010

Jermaine O'Neal actually almost went to San Antonio when he re-signed with the Indiana Pacers in the summer of 2003, and perhaps he should have. Instead of teaming up with Tim Duncan and winning at least one ring if not several more, he got mixed up in the Malice at the Palace incident in 2004-05, and after that battled constant injury problems. Before his contract expired in 2010, O’Neal had been traded twice and seen his averages plummet from a nightly 20-10 to something closer to 13-7.

Team: Cincinnati Reds
Contract value: Nine years, $116.5 million
Years: 2000-2008

When Ken Griffey, Jr. decided to sign with the Cincinnati Reds, it looked like one of the biggest free agent coups in history. Really, it’s almost impossible to overstate how big a star Griffey was; in Seattle, he had amassed 10 All-Star appearances, 10 Gold Gloves, and an MVP award. At age 29, he had already hit 398 career home runs. It looked like he was going to go down as one of the greatest players ever. Then he got to Cincinnati, and everything changed. Griffey averaged 110 games per season, made only three All-Star teams, and never made the playoffs.

Team: Detroit Tigers

Contract value: Nine years, $214 million

Years: 2012-2020

Burly, power-hitting first basemen do not age well. History has proven this to be true time and again. And yet, for whatever reason, baseball teams continue to give people like Prince Fielder massive contracts. How much did the Detroit Tigers regret their pact with Fielder? They traded him to Texas last winter after just one season in the Motor City. It kind of makes sense why, though: Fielder went from averaging 37 home runs per season to just 25 last year, and at age 30 it’s unlikely he’s going to suddenly see a surge in his power numbers.

Team: Los Angeles Angels of Anaheim

Contract value: 10 years, $240 million

Years: 2012-2021

You know it’s not a good sign when the second you sign a contract, the universal reaction is “what were they thinking?” That’s basically what happened when the Angels signed Albert Pujols, and it’s easy to see why. In what sport is it a good idea to hand a 32-year-old a 10-year deal with 100 percent of the money guaranteed? Pujols has, predictably, not lived up to his astronomical billing; in three seasons in L.A. he has yet to make an All-Star team after doing so nine times in St. Louis and his power numbers have declined precipitously. But hey, only seven years to go!

Team: Atlanta Hawks
Contract value: Six years, $123.7 million
Years: 2010-2017

The Atlanta Hawks couldn’t really be blamed for handing Joe Johnson an absolutely enormous contract in the summer of 2010. They wanted a superstar, and had an All-Star in Johnson to whom they could offer more money than any other team in the NBA. They did, and to be fair Johnson produced solid numbers at the outset of the deal. He has been an All-Star in three of the four years of the deal, although the Hawks obviously didn’t think much of that and traded him to the Nets in 2012. Johnson has seen his scoring average and shooting percentages discernibly dip from those in his prime, and with two years and about $48 million to go on the deal, it’s only going to become more of an albatross.

Team: Dallas Mavericks

Contract value: Seven years, $102.3 million

Years: 2001-2008

A sharpshooter who helped spark Dallas’ rise to respectability, Michael Finley earned a huge extension after making back-to-back All-Star teams in 1999-2000 and 2000-01. The honeymoon didn’t last, though, as Finley’s performance began to decline and the Mavericks decided to amnesty him in the summer of 2005. When a team would rather eat almost $52 million over three years just to not have you on the roster, it's never a good sign.

Team: New Jersey Devils

Contract value: 15 years, $100 million

Years: 2010-2025

The case of Ilya Kovalchuk is certainly a strange one. The New Jersey Devils thought they were locking up a franchise cornerstone by signing him first to a 17-year deal before—when that was rejected by the NHL—settling on a 15-year contract. However, just three years into the deal, Kovalchuk decided to retire from the NHL at age 30. He wasn’t done playing hockey, just done with America, which had to leave the Devils a bit frustrated. While they no longer had to pay him, they did have to replace one of their best players.

Team: New England Patriots

Contract value: 10 years, $103 million

Years: 2001-2010

While the New England Patriots were coming off a brutal 5-11 season under first year head coach Bill Belichick, there was optimism in the air when they locked up franchise quarterback Drew Bledsoe to a deal that would make him a “Patriot for life.” It turns out that “for life” actually means “less than a year,” as during the second game of the 2001 season Bledsoe would get injured, be replaced by a backup named Tom Brady, and shipped out of New England all in a span of 12 months. While he did make the Pro Bowl in his first season with the Buffalo Bills, Bledsoe struggled after that and retired following the 2006 season.

Team: Dallas Cowboys

Contract value: Six years, $108 million

Years: 2014-2019

Oh, Tony Romo. It’s not that the Dallas Cowboys’ quarterback isn’t good. He is. But he just has a penchant for making the worst possible plays in the worst moments. Nobody forgets the fumbled snap in the playoff game against Seattle, but how about in the first year of his massive contract extension going out and throwing three interceptions in the first half of his first game? Somehow, it doesn’t feel like this deal is going to end with anybody happy.

Team: Los Angeles Dodgers
Contract value: Seven years, $105 million
Years: 1999-2005

Kevin Brown was a trailblazer in baseball, the first man ever to receive a $100 million-plus contract. The Los Angeles Dodgers certainly thought they were getting a great deal, as the 33-year-old was coming off a season in which he had been an All-Star and posted a 2.38 ERA with the San Diego Padres. His first two years in L.A. went well, but soon injuries began to take their toll and Brown quickly devolved into an average pitcher at best. Later, he would be named by the Mitchell Report as one of the biggest steroid users on the Dodgers.

Team: Washington Bullets
Contract value: Seven years, $105.4 million
Years: 1996-2003

Juwan Howard made exactly one All-Star team in his career, but he sure picked the right year to do it. Posting a career-best 22.1 points per game, Howard entered free agency with a ton of leverage and earned a huge offer from the Miami Heat. It turns out the Heat were actually way over the cap and weren’t allowed to sign Howard, which meant he could return to Washington under a huge new contract despite having only spent two seasons in the NBA. Howard never reached his 1996 levels again, posting solid averages but playing for three different teams over the life of the deal.

Team: Cleveland Cavaliers
Contract value: Seven years, $107 million
Years: 1997-2004

Let’s hope signing LeBron works out better for Cleveland than it did with Shawn Kemp. Coming off a tremendous 1996-97 season, Kemp wanted a raise but was denied by Seattle. They in turn flipped him to Cleveland in a three-team trade, and once there he got the huge extension he wanted. And until the lockout, everything was fine. But then Kemp got enormously fat, lost his athleticism, and soon lost his ability on a basketball court.

Team: Baltimore Ravens
Contract value: Six years, $120.6 million
Years: 2013-2018

Perhaps nobody has timed a contract push better than Joe Flacco. The Baltimore Ravens’ quarterback knew he’d be entering free agency following the 2012 playoffs, and in his four playoff starts threw 11 touchdown passes and 0 interceptions as the Ravens won the Super Bowl. Since then? He has thrown more interceptions (23) than touchdowns (20), has been sacked 51 times, and gone 8-9. Not a great return on investment.

Team: Colorado Rockies
Contract value: Eight years, $121 million
Years: 2001-2008

Those Denver schools must really be something. At least, that’s why Mike Hampton claimed he signed with the Colorado Rockies in 2001, despite having to play in the pitcher’s hell known as Coors Field. Unsurprisngly, Hampton’s stint in Colorado was a complete disaster; he lasted just two seasons, posting an ERA of 5.75 in 62 starts before he was traded to Atlanta and began to salvage his career before being felled with elbow problems that led to Tommy John surgery.

Team: Philadelphia Phillies
Contract value: Five years, $125 million
Years: 2012-2016

Ryan Howard was already in decline when the Philadelphia Phillies signed him to a ridiculous $25 million per year extension, and the slugging first baseman has done little to reverse that downward trend. He spent the first two years of the extension battling injuries and hitting just 25 home runs combined. This season has been midly better, except he is posting a pitiful .310 OBP and is slugging just .384, easily the worst numbers of his career. The idea of having to pay this guy another $50 million has to keep Phillies executives up at night.

Team: San Francisco Giants
Contract value: Seven years, $126 million
Years: 2007-2013

Another “whoa” contract belonged to Barry Zito, who immediately upon signing with the San Francisco Giants lost the form that won him the Cy Young Award in 2002 and made him an All-Star three times with the Oakland A’s. Zito was never the ace the Giants had expected, battling injuries and posting a combined 4.62 ERA over his seven seasons in San Francisco. He did slightly redeem himself, though, by pitching masterfully and earning the win in Game 1 of the 2012 World Series.

Team: Toronto Blue Jays

Contract value: Seven years, $126 million

Years: 2008-2014

At no point did the Blue Jays’ extension with Vernon Wells make any sense for the team. Wells was certainly a good player, with two All-Star selections and lifetime averages of 26 home runs and a .281 batting average per season. But paying a player like that $18 million a year just didn’t make any sense, and that’s probably why the Blue Jays soon realized their mistake and sent Wells to the Angels via trade in 2011.

Team: Orlando Magic
Contract value: Six years, $126 million
Years: 2007-2013

It’s unclear what the Magic’s long-term vision was when they acquired Rashard Lewis in a sign-and-trade during the summer of 2007. This is what happens when teams have too much cap space for their own good, it seems. Lewis was a solid scorer in Seattle, putting up three consecutive 20-plus PPG seasons before hitting free agency. He never reached those numbers in Orlando, falling all the way to 11.7 PPG as he was traded straight up for another bad contract in Gilbert Arenas during the 2010-11 season.

Team: New York Mets
Contract value: Six years, $137.5 million
Years: 2008-2013

When they signed Johan Santana, the New York Mets thought they were getting the pitcher who had won two of the last four Cy Youngs and was a three-time All-Star with the Twins. Instead, what they got was a total of 109 starts over six years and a never-ending parade of injuries. Santana did throw the first no-hitter in Mets history in 2012, but also missed all of 2011, part of 2012, and all of 2013 with a shoulder injury.

Team: Boston Red Sox

Contract value: Seven years, $142 million

Years: 2011-2017

There really was not a single moment where Carl Crawford’s stint with the Boston Red Sox went well. He got off to a very slow start in 2011, and the fickle Red Sox fans quickly turned against him. He then injured his wrist in the winter and didn’t even make his season debut until July of 2012. About a month later, he went out for the season with Tommy John surgery, and just a week later he was traded to the Dodgers. While he has been better with the Dodgers, Crawford has been a shadow of the game-changing force he was in Tampa Bay.

Team: Atlanta Falcons
Contract value: 10 years, $130 million
Years: 2005-2014

The Falcons’ commitment to Michael Vick was never symbolized more than when team owner Arthur Blank pushed the injured Vick along the sidelines in a wheelchair after the quarterback and broken his fibula in 2003. Vick repaid the Falcons’ commitment by funding and running a dogfighting ring out of his home in Virginia, which eventually led to him being sent to jail and the contract being voided.

Team: Washington Wizards
Contract value: Six years, $111 million
Years: 2008-2013

It’s not Gilbert Arenas’ fault that the Washington Wizards handed him a huge contract right after a knee injury limited him to 13 games the season before. And it’s not his fault that while still recovering in 2008-09, he only played in two games all year. But what was Arenas’ fault was when he decided to bring a gun into the locker room to threaten a teammate in 2009-10. Regardless of who gets the blame, nobody can question that this deal is among the worst signed in the history of the NBA.

Team: New York Knicks

Contract value: Six years, $100 million

Years: 2001-2007

When a rule that allows a team to get rid of a terrible contract is named after you, that’s not a good sign. The “Allan Houston Rule,” more commonly known as the amnesty provision, was created because of how bad the New York Knicks’ deal with Houston was. While they didn’t actually use the amnesty on Houston, the Knicks were forced to pay him to sit and do nothing as he missed 32 games in 2003-04, 62 in 2004-05, and went into retirement in October of 2005.

Team: Washington Redskins

Contract value: Seven years, $100 million

Years: 2009-2016

Albert Haynesworth had shown that he was maybe not the most stable person in the world when he stomped on offensive lineman Andre Gurode’s face during a 2006 game. That didn’t stop the Washington Redskins and their free agent-happy owner Dan Snyder from handing him a huge contract in the 2009 offseason, though, following Haynesworth’s back-to-back Pro Bowl campaigns with the Titans. So what did they get in return? A sub-par 2009, failed fitness tests, and a public war of words with coach Mike Shanahan. Haynesworth recorded just 13 tackles in 2010, and was placed on the restricted list in December. He played one more season in the NFL before everybody realized he was not worth the trouble.

Team: New York Yankees

Contract value: 10 years, $275 million

Years: 2008-2017

No matter how much Alex Rodriguez produced at the plate, he was always going to have a hard time living up to his criminally insane $27.5 million per year salary. He did help the Yankees win the World Series in 2009, but everything since then has basically been a non-stop blooper reel. He admitted to using steroids and—gasp!—lying to Katie Couric about it, then was suspended for the entire 2014 season for his role in the Biogenesis scandal. With his production in steady decline (he is 38, after all), A-Rod still has three seasons and $61 million to go on his contract. Enjoy, Yankees fans.