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Top 5 Worst Contracts In Tri-State Hockey History

We will begin with hockey as we look at the top five worst tri-state hockey contracts in history. And here’s a warning…you may see the New York Rangers mentioned more than you think and I’m a Rangers fan.

In sports, there is a constant arms race to get the best possible players on your team. Some teams choose to get better gradually and draft extremely well and develop players. Another way teams choose to build their rosters is through spending money on players from other teams. Some general managers choose wisely and spend their money smartly while others frivolously throw money around like Floyd Mayweather on a shopping spree.

For teams in the tri-state area, it seems that many of the GM’s throughout history have a tendency to spend money but not always in the right ways. When the discussions of bad contracts in sports come up, New York and New Jersey teams are always near or at the top of those conversations. With that said, we will look at the worst contacts in tri-state sports history in the three major sports in the area. We will begin with hockey as we look at the top five worst tri-state hockey contracts in history. And here’s a warning…you may see the New York Rangers mentioned more than you think and I’m a Rangers fan.


Al Bello/Getty Images

Al Bello/Getty Images


T-5. Chris Drury, New York Rangers- 5-year/ $35.25million in 2007

This is the beginning of a theme for the next few lines of this article. Drury was a major signing for the Rangers along with Scott Gomez (more about him later). Prior to signing with the Rangers, Drury had accumulated 464 points with 193 goals in eight seasons. The Rangers believed that Drury teamed up with Gomez would lead a great 1-2 punch of offense for a team that was searching for goals. Well…that never happened.

Four years with the Rangers and his highest goal total was 25 in his first season with the team. After that season, Drury’s game took a steep turn downward as his points and goals decreased for the next three years of the contract. The Rangers eventually bought out Drury’s deal in 2011 and he soon retired after.


T-5. Bobby Holik, New York Rangers- 5 year/ $45 million in 2002

Many Ranger fans believe that Holik was let go by the Devils so that the Rangers could pick up a player that was passed his prime. For the most part, Holik played some great hockey with the Rangers during his time with the team.

In two seasons, Holik scored 41 goals and had 91 points with the Rangers during the two seasons of the contract. The problem was that the Rangers did not make the playoffs in those two seasons Holik was there. Then the NHL Lockout happened which took the entire 2004-2005 season. After the lockout and the creation of a salary cap in the NHL, the Rangers bought out the remainder of Holik’s contract which ended Holik’s good but unfulfilling stint with the team.


  1. Brad Richards, New York Rangers- 9 year/ $60 million in 2011

Richards was signed and was reunited with former coach John Tortorella who he won a Stanley Cup with in Tampa Bay in 2004. While Richards had decent numbers with a contract-high 66 points in his first season with the team, it always seemed that Richards didn’t fit with the team, the city or his former Stanley Cup winning coach, who on numerous occasions either scratched Richards or threw him on a fourth line. And while his numbers were good, the Rangers were not paying for good. They paid $60 million over nine years for great and they never really saw great.

A last ditch effort for Richards to resuscitate his Ranger career was during the 2014 NHL Playoffs as he scored five goals and 12 points during the Rangers run to the Stanley Cup Final. It was too little too late as Richards was bought out by the Rangers in the summer of 2014.


  1. Scott Gomez, New York Rangers- 7 years/ $51.5 million in 2007

This is the one that hurts. While 70 and 58 points seem good to some, Gomez hit 80-plus points just a couple of seasons before signing with the Rangers. As mentioned earlier, Gomez and Chris Drury were supposed to be the two that would lead the Rangers to the playoffs and maybe even beyond. The Rangers did make the playoffs in both seasons with Gomez with a first-round win in year one and a seven game series loss in year two of the Gomez/Drury experiment.

In the summer of 2009, the Rangers began to clear salary and Gomez and/or Drury were on the chopping block. The Rangers held on to Drury (no idea why) but traded Gomez to the Montreal Canadians to end the pain.


  1. Ilya Kovalchuk, New Jersey Devils- 15 years/ $100 million in 2010

This was the contract that shocked everyone. The Devils have always been known to be a little…cheap when it came to signing free agents. Kovalchuk was traded from the Atlanta Thrashers to the Devils in February 2010 and he proceeded to score 27 points in 27 games for New Jersey. In the summer of 2010, Kovalchuk became a free agent and while many assumed that he would go to the highest bidder nobody expected the highest bidder to be the Devils…to the tune of a 17 year/$102 million contract.

The initial contract was not approved by the NHL due to the Devils frontloading the first few years of the contract and leaving the remaining years worth almost nothing to help future salary numbers. They agreed to a 15 year/ $100 million deal that summer and it worked out well for the Devils for three seasons…that is until he abruptly retired from the NHL and began playing professionally in his native country of Russia. This one contract cost the Devils $3 million and a loss of three draft picks (the penalties were eventually lessened) all for a player to just quit and go home with 12 years left on a contract.


  1. Rick DiPietro, New York Islanders- 15 years/ $67.5 million in 2006

Number one was a tough decision. Kovachuk’s contract was by far the costliest contract in the NHL for the Devils but DiPietro’s was just above and beyond dumb.

A former number one overall draft in 2000 by the Islanders, DiPietro was highly touted goaltender coming out of Boston University. After a shaky first two seasons in the NHL, DiPietro began playing close to his potential even going 30-24-5 during the 2005-2006 season. Even with that season, DiPietro only had a career record of 58-62-5 at that point. But new Islanders general manager and former goalie Garth Snow took that record to mean that DiPietro was a no-brainer and signed him to a 15-year contract worth over $67 million. One NHL executive responded to what the contract meant to the NHL with the quote, “It means the owner is a moron.”

One All-Star appearance withstanding in 2008, DiPietro never lived up the contract with the list of injuries he suffered almost as long as the length of the contract. Concussions and knee issues hampered DiPietro’s career which was average at best. He ended his career with a 130-136-36 record in his 11 seasons on Long Island. DiPietro’s name still comes up as one of the worst deals ever constructed in the hall of bad contracts with people still trying to figure out the logic. On the brightside, DiPietro is beginning a new career in broadcasting with ESPN Radio NY and on MSG. However he should try to stay away from Nassau Coliseum if possible.

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Kahlil Thomas

Kahlil is the College Sports Editor for as well as a columnist, hosting the Bump 'N Run column once per week. He also co-hosts a weekly basketball podcast, The Box Out, every Thursday evening with fellow writer Jason Cordner.
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