The 25 Worst Contracts In Sports History

Image via Complex Original

Sports and big contracts have gone hand-in-hand for several decades now. Each year it seems like new records for athlete contracts are set, and expectations for the upcoming season are raised. However, as we all know, ridiculous dollar amounts can sometimes lead to epic fails on the field of play. Whether due to injury (we see you, Luis Castillo), laziness (you too, Eddy Curry) or even legal problems off the field (what up, Mike Vick) a number of issues can turn deals that once seemed sweet into sour ones with long-lasting aftertastes. So, in honor of Labor Day and all the hard-working Average Joes who dream of seeing six-figure salaries (much less eight or nine-figure ones), here are the 25 Worst Contracts in Sports History...

25. Mo Vaughn

Year: 1999
Contract: $80 million/Six years
Team: Anaheim Angels
Mo Vaughn's 40 home runs and 100-plus RBI seasons with the Red Sox made many consider him one of the Greatest Fat Baseball Players of All Time. Those numbers also got him the biggest MLB contract in the league in '99, but two productive yet non-stellar seasons with Angels, a season-ending knee injury, and battle with the bulge made those glory days in Boston a distant memory. He was later traded to the Mets where he continued to decline and ruin his rep. Oh yeah, that mention in the Mitchell Report years later didn't help either.

24. Kei Igawa

Year: 2006
Contract: $20 million/Five years
Team: New York Yankees
In Japan, Kei Igawa had a career record of 86-60 with a 3.14 ERA, making him one of the most sought-after Japanese players in recent history. The Yankees won the bidding war by putting up over $26 million to begin negotiating a contract with Igawa. In the years since signing his contract, the lefty has gone 2-4 with a 6.66 ERA and has spent far more time in the minor leagues than in Yankee pinstripes. His salary stretched out over major league innings pitched has equated to over $640,000 per inning. What's the Japanese translation for "Don't believe the hype?"

23. Per Kroldrup

Year: 2005
Contract: £5 million/One season
Team: Everton
In any sport, injuries remain the biggest threat to star athletes and the big contracts they receive. After Everton paid a hefty £5 million transfer fee to acquire Per Kroldrup from Udinese, the skilled Danish defender suffered a groin injury that required surgery. Kroldrup ended up only making one appearance in his year spent with the club. Grand opening, grand closing. *Hova voice*

22. Carl Pavano

Year: 2004
Contract: $39.95 million/Four years
Team: New York Yankees
Not much can be said about Carl Pavano that the stats don't already make pretty obvious. Over three seasons with the Yankees, homie went 9-8 with and ERA of 5.00. He also went to the DL with everything from broken ribs to a bruised buttocks. Calling this signing a pain in the ass for Yankees fans would be an understatement.

21. DeAngelo Hall

Year: 2008
Contract: $70 million/Seven years
Team: Oakland Raiders
After trading draft picks to Atlanta in order to get Hall, the Raiders sealed the deal with this ridiculous contract that included $24.5 million guaranteed. Hall was "unable to adapt to the Raiders' man-to-man style of defense" a.k.a. fam was getting torched on the regular by wideouts all over the league. By November he was released by the Raiders, who did so to avoid having to pay an additional $16.5 million in injury-guaranteed bonuses. Hall made $8 million in eight games played. SMH, yet they let Nnamdi Asomugha get away for less money overall this offseason.

20. Danny Tartabull

Year: 1992
Contract: $27 million/Five years
Team: New York Yankees
Danny Tartabull capitalized on his contract year in 1991 by having the sole All-Star season of his 14-year career. In the offseason the Yankees came calling and made him one of the highest paid players in the MLB. Tartabull would never produce in New York like he had with the Kansas City Royals and was often the subject of public ridicule via George Steinbrenner. It's safe to say the highlights of dude's time in New York were those two cameo appearances he made on Seinfeld.

19. Wade Redden

Year: 2008
Contract: $39 million/Six years
Team: New York Rangers
It was no secret that Wade Redden's numbers were on the decline in Ottawa as he entered free agency in 2008. So, why the Rangers thought he could somehow revive his career under the lights of the Big City we have no clue. As expected, Redden's numbers continued to drop and his time on the bench increased. Now the Rangers owe him millions through 2014. Is it us or do New York teams just love trickin' on overrated athletes no matter the sport?

18. John Koncak

Year: 1989
Contract: $13 million/ Six years
Team: Atlanta Hawks
Jon Koncak never made an All-Star team and only spent nine years in the league, but he made history in the short time he was there. As a reserve, his unheard of $13 million six-year contract at the time earned him more than Magic Johnson, Michael Jordan, and Larry Bird. SMH, all that and they couldn't even spell dude's name correctly.

17. A.J. Burnett

Year: 2008
Contract: $82.5 million/Five years
Team: New York Yankees
Never the type to miss out on scooping up big free agents, the Yankees targeted A.J. Burnett who had gone 18-10 and led the AL with 231 strikeouts while in Toronto the previous season. With the Yankees, Burnett has gone 32-25 and recorded a 4.81 regular season and 5.67 postseason ERA. Oh yeah, then there's that time in 2010 when he punched a door after a loss injuring his hand in the process. Classy.

16. Denílson de Oliveira Araújo

Year: 1998
Contract: 21.5 million
Team: Real Betis
When Real Betis made Denilson the highest-paid soccer player in the world, the last thing they expected was for their squad to go from the highest level of competition down to the Second Division (think going from the MLB to the minors). But that's exactly what happened only a year after signing the Brazilian World Cup winner. Even while playing at a lower-level, Denilson failed to produce for the team and was considered a liability before finally being sold to the French Club Girondins de Bordeaux in 2005. Even la joga bonito has it's share of ugly contracts.

15. Michael Vick

Year: 2004
Contract: $137 million/Ten years
Team: Atlanta Falcons
Usually it's lackluster performance or injuries that have owners regretting big contracts to athletes. However, for Arthur Blank it was Vick's federal charges and subsequent sentencing for dog fighting that screwed over the Falcons. The team attempted to have Vick repay $20 million, arguing that he had breached his contract. But after legal wrangling, Vick was only ordered to repay $3.5 million of the $35 million he received in the first two years of the contract. Years later and Vick has another $100 million contract and the Falcons are back to being a contender. #timehealsallwounds

14. Ben Wallace

Year: 2006
Contract: $60 million/Four years
Team: Chicago Bulls
Ben Wallace was a four-time Defensive Player of the Year and played a pivotal role in the Detroit Pistons winning a championship in 2004. However, those days of shutdown defense seemed like a distant memory during his two-year tenure with Chicago. Plagued by injuries, Big Ben averaged five points, 9.7 boards, and two blocks per game before being traded to the Cavs in 2008. See, good D isn't everything. Pause.

13. Stephon Marbury

Year: 2003
Contract: $76 million/Four years
Team: Phoenix Suns/New York Knicks
Coming off a season in which he made his second All-Star team and posted respectable stats of 20 points and eight rebounds per game, Marbury signed a contract extension with the Suns only to be traded to the Knicks three months later. After maintaining his 20 and eight average in the first season and a half with the Knicks, the nightmare began. Clashes with both Larry Brown and Isiah Thomas, a sex scandal, and a straight-up refusal to play at some points resulted in the Knicks paying Marbury $21.9 million to not play at all in 2009 before he was traded to the Boston Celtics. Oh yeah, did we mention that Starbury negotiated this $76 million contract without an agent? #mindfucked

12. Luis Castillo

Year: 2007
Contract: $25 million/Four years
Team: New York Mets
Signing an injury prone 32-year-old to a long term contract is just the kind of fuckery the New York Mets became known for in the late 2000s. Sadly (for Mets fans at least), it's also the kind of nonsense they perpetrated in the early 2000s, mid '90s, early '90s, early '80s, mid and late '70s...you get the picture.

11. Jim McIlvaine

Year: 1996
Contract: $33.6 million/Seven years
Team: Seattle SuperSonics
In the 1996 offseason, the SuperSonics were looking to add one more piece to their team which had just lost in six games to the Chicago Bulls in the Finals. Already led by Gary Payton and Shawn Kemp, the Sonics front office looked to 7-foot-1 Jim McIlvaine to fill their void at center. Of course giving $33 million to an unproven center pissed off Shawn Kemp who had been asking the team for a new contract after helping lead the Sonics to the playoffs for the previous six seasons. McIlvaine averaged 3.8 points and four rebounds per game in his first season with Seattle. Kemp's continuing frustration led to him being traded to the Cavs in the '97 offseason and the Sonics never made it to the NBA Finals or past the second-round again. Did McIllvaine have a big impact? Yup. The kind the Sonics were looking for? Fuck no.

10. Bobby Bonilla

Year: 1992
Contract: $29 million/Five years
Team: New York Mets
In 1992, Bobby Bonilla had just finished a season in which he made his fourth consecutive All-Star team and his third Silver Slugger award. But in his first season after signing with Mets, Bonilla's batting average dropped more than 50 points. Besides 1994, his numbers never really lived up to the potential he showed while in Pittsburgh. He was traded to the Orioles in 1995 but that wasn't the end of Bonilla's tumultuous relationship with the Mets. In 2000 it was revealed that "The Mets agreed to pay out the remainder of Bonilla's contract by deferring the $5.9 million that he was due. The Mets will pay him 25 equal payments of $1,193,248.20 every July 1 from 2011 until 2035, assuming an annual interest rate of 8% during the period 2011-2035." If Bonilla was an ex-girlfriend of the Mets, that contract was the illegitimate baby that requires beastly child support payments. Not that we've experienced that kinda thing...

9. Albert Haynesworth

Year: 2009
Contract: $100 million/Seven years
Team: Washington Redskins
Nine-figure contracts are pretty rare in sports, nine-figure contracts for defensive linemen are unheard of. Albert Haynesworth became the highest-paid defensive player in NFL history when he inked his deal with the Redskins after back-to-back Pro Bowl seasons in Tennessee. Haynesworth complained about the defensive scheme in '09 but things came to a boiling point during the 2010 training camp when the lineman refused to show up to practice and publicly clashed with head coach Mike Shanahan. Fat Albert would go onto post career-lows in tackles (13) and sacks (2.5) before being suspended for the rest of the season in December. During the offseason he was traded to New England for a fifth-round draft pick. (Insert HaynesWORTH-less joke here) #tooeasy

8. Vin Baker

Year: 1998
Contract: $87 million/Seven years
Team: Seattle SuperSonics
After putting up All-Star stats (19 points and eight rebounds per game), the Sonics rewarded Baker with one of the biggest contracts in the league at the time. Baker rewarded them by only playing in 34 games in the first year of his contract. The remaining years would be plagued by his battles with the bulge and the bottle before he was traded to the Celtics in 2002.

7. Alexei Yashin

Year: 2001
Contract: $87.5 million/Ten years
Team: New York Islanders
Yashin had an average of 38 goals per season over the his last four years in Ottawa, but a 10-year contract for a 28-year-old player with whispers about his lack of dedication was ridiculous—even by New York sports standards. Yashin's production faltered in his years with the Islanders and he recorded a career-low in 2003-04 only scoring 15 goals that season. New York bought him out of his contract in 2007 for $17.63 million. Yashin's annual $3.2 million hit on the team's salary cap will be felt through 2015. Ouch.

6. Mike Hampton

Year: 2001
Contract: $121 million/Eight years
Team: Colorado Rockies
When the Rockies gave Mike Hampton the largest contract in sports history at the time, they figured they would be getting the same dominant groundball pitcher who had gone 22-4 with a 2.90 ERA in 1999. However, once Hampton got to Coors Field he went 21-28 with a 5.75 ERA over two seasons before being dealt to the Braves. Pretty shitty for the same dude who said he chose to go to Colorado "for the school system." FOH, Mike.

5. Barry Zito

Year: 2006
Contract: $126 million/Seven years
Team: San Francisco Giants
The 2002 Cy Young Award winner had three All-Star seasons in Oakland but was he deserving of the biggest pitching contract in MLB history at the time? The San Francisco Giants thought so and agreed to pay the lefty $18 million per year. Since then, Zito has put up a record of 43-61 with an ERA of 4.52. The agent behind such a ridiculous contract? None other than Scott Boras. Yup, we're pretty sure dude has this on repeat anytime he thinks about the Zito deal.

4. Jerome James

Year: 2005
Contract: $30 million/Five years
Team: New York Knicks
It's safe to say that no player in the history of pro sports has benefited from the contract year phenomenon quite like Jerome James. Hell, this dude didn't even put up a whole year (or half of one) of stellar stats in order cash in on a big contract. All it took for James was two playoff series. While with the SuperSonics, James tripled his regular season stats in the 2004 playoffs posting 12.5 points and 6.8 rebounds in series against the Kings and Spurs. After his signing, James showed up to the Knicks training camp out of shape and spent most of his first season injured or on the bench. Things never improved as James continued to show poor performance in the few minutes that he did play and a lack of conditioning during team practices. The low-point came in the 2007-08 season when James earned $5.8 million for a season in which he played in only two games for a total of five minutes. SMH, at least he lived up to the "Big Snacks" nickname.

3. Oliver Perez

Year: 2009
Contract: $36 million/Three years
Team: New York Mets
Two biggest fears of GMs after giving out big contracts? Injuries and laziness. After signing Oliver Perez, the Mets got a big dose of both. Only three months after signing his $36 million contract, Perez went on the DL with patellar tendinitis. He made his return to the rotation in July only to have the same issue of patellar tendinitis come up again in August; this time requiring season ending surgery. In June 2010, Perez made another return to the DL with...wait for it...patellar tendinitis! After another frustrating season of injuries and refusal to do minor league work, the Mets released Perez in March 2011 still owing him another $12 million. Just another one of the many Mets Fails over the years.

2. Darren Dreifort

Year: 2001
Contract: $55million/Five years
Team: Los Angeles Dodgers
Why the Dodgers thought Darren Dreifort, a pitcher with a career record of 39-45 who had a well-known history of arm injuries deserved such a mega deal, we'll never know. Dreifort was plagued by arm and shoulder injuries almost immediately after signing his big contract and ended up only pitching in three of the five seasons on his contract. The legendary Scott Boras is a better hustler than your favorite rapper ever claimed to be.

1. Eddy Curry

Year: 2005
Contract: $60 million/Six years
Team: New York Knicks
Eddy Curry's deal was just another big contract that came in an era where the Knicks seemingly just threw millions of dollars to players who hadn't really proved their consistency. During his tenure with the Knicks, Curry routinely showed up to camp out of shape and showed a lack of effort that was reflected in career lows. One of his lowest points came in the 2008-09 season when he only played in three games and scored five points total for the season.