Worst Professional Contracts of All-Time

Investments that never work out, for the team that is…

Negotiating a contract is always challenging for both a front office and a player. Long term deals often come with risk as front offices try to maximize a player prime years where they expect the most money.

Like many deals on this list, they leave teams with a contract they can not move as they pay for a performance that they never received. This list of sticky contract situations accurately summarizes the worst of the worst

1. Bobby Bonilla

Source: StephenDunn.com

Bobby Bonilla last stepped on a baseball field during the 1999 season, wherein 60 games he hit .160. Until 2035 however, he will be paid $1.2 million a year, which made him the 20th highest-paid player on the Mets roster in 2019.

After the 1999 season, the Mets were looking to rebuild and Bonilla was not in their future plans. The Mets still owed Bonilla $5.9 million for the 2000 season but did not outright release him. The team and Bonilla’s agent agreed to add an 8 % annual interest on the money from 2000-2011 which added up to $28.9 million. At one point, Bonilla was making more than Jacob Degrom, Steven Matz, and Noah Syndergaard to not play.

2. JaMarcus Russell

Source: Iconsportswire.com

In the 2007 NFL draft, the Oakland Raiders took Russell with the first overall pick. While the Raiders thought they had their franchise QB Russell’s tenure got off to a rocky start. He missed training camp before signing a six-year $68 million deal. The contract came with $32 million guaranteed and was the richest rookie deal in NFL history.

Russell, however, would turn into arguably the biggest bust in NFL history. In three seasons with Oakland, Russell was able to record just seven wins and 4,083 passing yards. Russell finished his career with more interceptions than touchdowns and never recorded more than two touchdowns in a game.

3. Rick Dipetrio

Source: USATodaysports.com

In 2006 the New York Islanders signed Rick Dipetrio to a 15-year deal worth $67.5 million. At the time it was the longest contract ever given to a player and would remain historic for the wrong reasons.

The Islanders thought they had found their franchise goalie in Dipietro. Injuries, however, began piling up just two years after the deal had been signed. During his career, the Islanders did make it to the postseason three times. In the playoffs, Dipietro went 2-7 , however, only one of those appearances came after the extension. Dipietro was ultimately cut in 2013 and will be paid 1.5 million annually through  2029 not to play for the Islanders.

4. Gilbert Arenas

Source: USAToday.com

In 2008 the Washington Wizards surprised the NBA world by signing Gilbert Arenas to a six-year extension $111 million deal. Arenas were coming off an injury-riddled season when he had appeared in just 13 games. His problems in Washington, however, would go beyond injuries.

After signing the extension, Arenas appeared in just 51 games for Washington from 2008- 2010 before being dealt to the Magic midway through the 2010- 2011 season. During the 2010- 2011 season, he shot 36.6 % from the field, which would have ranked him last in the NBA if he had enough shots to qualify. He was also suspended during the 2010 season for bringing guns to the Wizards locker room.

5. Chris Davis

Source: GregFlume.com

In 2016 the Baltimore Orioles and Chris Davis agreed to a seven-year mega-deal worth $161 million. At the time, Davis was coming off a league-leading 47 homerun campaign only two years after hitting a career-high 53. The deal seemed like a solid gamble for Baltimore but has become disastrous. Since 2015 Davis has hit more than 30 home runs once and has seen his playing time dwindle.

Additionally, over the past two seasons, David has failed to hit above .200 and struck out 331 times. His slugging percentage and OPs have both fallen by over 100 points while Davis only had 55 hits last season. From September 2018 to April 14th, 2019 Davis, set a major league record by going 54 at-bats without a hit.

6. Albert Haynesworth

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Following the 2008 season, the Redskins signed Haynesworth to a seven-year, $100 million deal. After leaving Tennessee, Haynesworth only lasted two years in Washington before being traded to New England.

In Haynesworth’s stint with Washington, he struggled mightily and only recorded 6.5 sacks along with 53 tackles. In his last year with the Titans, the defensive tackles had 51 tackles and 8.5 sacks. Haynesworth’s contract also came with $41 million guaranteed. During Haynesworth’s time in Washington, his work ethic was constantly called into question, causing him to clash with teammates and coaches. He was out of the NFL by 2011.

7. Carl Crawford

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In 2010 the Red Sox made a splash in free agency by signing Carl Crawford to a seven-year deal worth $142 million. In Tampa Bay, Crawford was known for his speed and ability to get on base. In  his first year with Boston, Crawford hit .255 which was the lowest mark of his career.  In 2012 he only appeared in 31 games due to injuries and was dealt to the Dodgers later that year in an August blockbuster deal.

In two years with the Red Sox, Crawford finished with a .260 average and 23 stolen bases. The deal came to represent the disaster that the 2010- 2011 teams were and his departure signaled a new era for the franchise. Crawford continued to struggle with the Dodgers and was released in 2016, with $34.6 million remaining on his contract.

8. Brock Osweiler

The Houston Texans took a leap of faith by signing Osweiler to a four-year deal worth $72 million in 2016. The Texans were hoping that the former Bronco could be the franchise quarterback they had been missing. The deal, unfortunately, turned out to be a disaster.

During Osweilers only season in Houston, the Texans went 8-6 and made the postseason. During the regular season, however, Osweiler lacked confidence and was unable to get on the same page with star receiver DeAndre Hopkins. In the playoffs, those struggles were amplified  against New England as he threw three picks and had a passer rating of 47.6 in a 34- 16 loss.

The following season Osweiler was dealt to the Browns for a second round pick by agreeing to take on Osweielrs contract.

9. Barry Zito

Source: BAS.com

When the Giants signed Zito to a seven-year deal worth $126 million in 2006, they thought they had their ace of the future. Zito was coming off a solid eight-year in Oakland, where he went 102-63. The Giant’s belief in Zito was reflected in the fact that his deal was the largest for a pitcher in MLB history at the time.

Zito, however, was never able to be that pitcher with the Giants as he struggled mightily. In 208 games for San Francisco, Zito went 63-80 with an ERA of 4.62. He only had one winning season in that span and failed to record an ERA lower than 4.03 in a single season. Although Zito did manage to win a ring in 2012, his time with the  Giants was filled with injuries and inconsistency.

10. Jay Cutler

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In 2013 Cutler signed a seven-year extension worth $126.7 million with Chicago. The Bears saw Cutler as their franchise QB, but it did not go as expected. During Cutler’s tenure, the Bears only made it to the playoffs once and lost in the NFC Championship game. His tenure was also full of drama, as his toughness was constantly questioned.

With Cutler under center, the Bears went 51-51. He led the league interceptions in 2014 with 18  and the Bears had one winning season after he signed his extension. Cutler was ultimately cut in 2017 as the Bears were able to save over $14 million against the cap.