The Top 25 Worst Contracts in Sports History
By nesbittandy1
We’ve seen a number of really, really bad deals in sports over the years. Some that have damaged teams for years.
Let’s count down the 25 worst deals of all time.
25. Jerome James, New York Knicks
Then-Knicks GM Isiah Thomas for some reason gave James a 5-year, $30 million dollar deal in 2005 after the center played well in two playoff series for the Sonics the season before. Injuries and weight issues limited him to just 90 games in four seasons with the Knicks before he was a part of a trade with the Bulls, who immediately released him.
16. Carl Pavano, New York Yankees
It’s hard to put it all on the Yankees for this one as Pavano was a highly coveted free agent after the 2004 season. But the Yankees did give him $39.95 million over 4 years and got just nine wins over four years as injuries cost him the entire 2006 and limited him to just 11 innings in 2007.
15. Mike Hampton, Colorado Rockies
Hampton was the most sought-after left-handed free agent after the 2000 season and cashed in on what was then the richest deal in baseball history with his 8-year, $121 million deal with the Rockies. The 2000 NLCS MVP went 21-28 in two years with the Rockies before being traded to the Marlins who then sent him to the Braves.
14. Alexi Yashin, New York Islanders
Yashin was a great player in the NHL when the Islanders acquired him in a trade in 2001. They immediately gave him a 10-year, $87.5-million contract, which was the biggest deal in NHL history at the time. After six seasons, including one in which he played just a few games due to injury, the Islanders bought out his contract and had to keep paying him millions until the end of the 2015 season.
13. DeAngelo Hall, Oakland Raiders
The Oakland Raiders traded for Hall before the 2008 season and gave him a 7-year, $72 million deal. Then eight games into the season and a 2-6 start they cut him. They paid him $8 million for the 8 games, a $7 million signing bonus, and a $1 million base salary. Hall then went back to the Redskins, a team he had played for before, and went to the Pro Bowl in 2010.
12. Matt Cassel, Kansas City Chiefs
Cassel cashed in after leading the Patriots to a 10-6 record after Tom Brady was injured in Week 1 of the 2008 season. He and the Chiefs agreed to a 6-year, $63 million deal with $28 million guaranteed. In four years with the Chiefs, Cassel only had one winning record and one trip to the playoffs before the team moved on after trading for Alex Smith.
11. A.J. Burnett, New York Yankees
The right-handed pitcher signed a 5-year, $82.5 million deal with the Yankees in December of 2008. Burnett, who turned 32 a few weeks after signing the deal, was supposed to team up with C.C. Sabathia to form one of the best rotations in the game. While he went 13-9 in his first year, he only went a combined 21-26 the next two years and was traded to the Pirates before the 2013 season.
10. Eddy Curry, New York Knicks
Isiah Thomas and the Knicks took a big risk bringing on Curry, who had been diagnosed with an irregular heartbeat during his time with the Bulls. The Knicks, however, traded for the big man and signed him to a 6-year, $60 million dollar deal in 2005. He averaged 19.5 points and 7 boards in his second year but then his numbers started falling off in his third year and he only played in 10 games over his fourth and fifth seasons in New York.
9. Rick DiPietro, New York Islanders
The sports world did a double take when it was announced the Islanders had signed their 25-year-old goalie to a 15-year deal worth $67.5 million in 2006. The 15 years was the longest playing contract in NHL history. Did he live up to the deal? No, no he didn’t. While had a couple of good years after the deal, injuries limited him to just 50 games from 2008-2013 and he was waived by the Islanders who bought out his contract. They still owe him $1.5 million a year until 2029.
8. Carl Crawford, Boston Red Sox
The Red Sox thought they had their next star left fielder when they signed Crawford to a 7-year, $142 million in December of 2010. Crawford, however, played just two seasons in Boston, hitting .255 his first year and playing just 31 games in his second season, before being traded to the Dodgers.
7. Barry Zito, San Francisco Giants
The Giants thought they were doing the right thing when they gave Zito a 7-year, $126 million deal in 2006. But boy did it go wrong in a hurry. Zito went from looking like an ace to having just one winning season (2012) with San Francisco.
24. Wade Redden, New York Rangers
The defenseman’s name does not sit well with Rangers fans, as for some reason the team’s GM at the time, Glen Sather, gave him $39 million over six years in 2008. Redden scored had just 5 goals and had 35 assists in his first two years with the Rangers, then he spent two years in the Rangers’ minor league system, and then had his contract bought out by the Rangers.
6. Josh Hamilton, Los Angeles Angels of Anaheim
The Angels surprised everyone when they signed Hamilton to a 5-year, $125 million deal in December of 2012. With Albert Pujols and Mike Trout already in the lineup, the Angels thought Hamilton would be the missing piece to help lead them to the World Series. Instead he struggled mightily with injuries and his battle with his drug addiction and ended up being traded back to the Rangers after just two lackluster years.
5. Albert Haynesworth, Washington Redskins
The Redskins wasted no time in signing Haynesworth after free agency started in 2009, signing the defensive tackle to a 7-year, $100 million deal that is widely considered the worst free agent signing in NFL history. Haynesworth lasted two just two years with the team, including just 8 games in his second season because the team suspended him for conduct detrimental to the team. He was then traded to the Patriots after the season.
4. Mo Vaughn, Los Angeles Angels of Anaheim
The Angels made a big move in November of 1998, making the former Red Sox slugger and 1995 AL MVP Vaughn the highest paid player in the game with a 6-year, $80 million deal. And it didn’t go well at all. Vaughn, who had hit over .300 in each of his last six seasons with the Red Sox, never hit over .300 in his time with the Angels, missed his third year entirely due to injury and then was traded to the Mets.
3. Gilbert Arenas, Washington Wizards
Arenas hit the lottery in July of 2008 when he signed a six-year, $111 million deal. He then played in just two games in the 2008-09 season due to injuries and was then suspended for most of the 2009-10 season due to a handgun violation. Arenas was later traded to the Magic in December of 2010, two years after signing that $111 million deal.
2. Michael Vick, Atlanta Falcons
The quarterback became the then highest-paid player in the NFL just two days before Christmas in 2004 when he signed a 10-year deal worth $130 million with a $37 million bonus. Vick was only 24 at the time so the deal made sense and what later happened could not have been predicted by anybody. Vick took his final snap for the Falcons just two years later (the Falcons went 15-17 in those years) before spending 548 days in jail after pleading guilty to a felony charge for dog fighting.
1. JaMarcus Russell, Oakland Raiders
The No. 1 pick of the 2007 draft got a 6-year, $63 million deal ($32 million guaranteed) after holding out through his first training camp and Week 1 of the season. He won just seven games and threw for 18 TDs and 23 INTs before being released after his third season. Russell, who battled weight issues throughout his career, has been called the biggest bust in NFL Draft history.
23. Denny Neagle, Colorado Rockies
Neagle signed a 5-year, $51 million deal with the Rockies in December of 2000 and then went 19-23 with a 5.56 ERA in his first two years. He missed most of the 2003 season and all of the 2004 season and then never pitched in the majors again.
22. Adam Archuletta, Washington Redskins
For some reason Redskins’ owner Daniel Snyder thought it would be a good idea to make Archuletta the highest paid safety in the NFL in 2006 with a 6-year, $30 million deal. He recorded just 60 tackles in his first and only year with the Redskins and then was out of the league a year later.
21. Bobby Bonilla, New York Mets
This deal is a classic. The Mets didn’t want to pay him $5.9 million dollars that they owed in him 2000 so they asked if he’d take deferred payments from 2001 to 2035 with an 8-percent interest rate on the money. Bonilla said yes, of course, and now on July 1 of every year he gets a nice $1,193,248.20 check from the Mets.
20. Jay Cutler, Chicago Bears
Smiling Jay Cutler signed a 7-year, $126 million extension with $54 million guaranteed in January of 2014. He played a total of 20 games over the next two years and retired from the game of football. Then he returned to football with a one-year deal (worth $10 million) with the Dolphins and finished the season 6-10.
19. Alex Rodriguez, New York Yankees
A-Rod to the Yankees was supposed to bring tons of championships to the Bronx. Instead, A-Rod made $317 million from the team and was a part of just one World Series winning team (2009).
18. Vin Baker, Seattle Sonics
Baker had some solid years behind him when Seattle gave the power forward a new 7-year, $86 million deal in 2000. Weight issues and injuries plagued him for the next two seasons and then he was traded to the Celtics. During his time with Boston he opened about being an alcoholic and was never the player he was once was when he won a gold medal at the Olympics.
17. Allan Houston, New York Knicks
The Knicks left everyone scratching their heads when they announced in 2001 that they had re-signed 30-year-old guard Allan Houston to a 6-year, $100 million deal. It was such a bad move that the NBA later made up a rule because of it, allowing teams to release an unproductive player and remove their salary from their luxury tax numbers. The rule’s name? The Allan Houston rule. Houston played out four years of the deal and only appeared in 70 games over the last two seasons before retiring after the 2005 season, though he was still the highest paid player in the league until after the 2007 season.