The Worst Free Agent Signings in NHL History

NHL free agency generates a large amount of excitement throughout the hockey world every year.

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In some cases, an NHL team will make a great signing, acquiring a player through a low term, low paying contract who brings unexpected results and production to his new team. Maybe they lead the club to a Stanley Cup or two.

Related: The Best Free Agent Signings in NHL History

On the other hand, NHL teams may sign a player to a long term contract which pays an extremely high yearly salary. For whatever reason, these contracts tend to be the least successful, as teams tend to get less than desired production and results from these players who have expectations of greatness placed upon them.

The following five players are among the most infamous free agent signings in NHL history.

Jeff Finger, Toronto Maple Leafs

As has long been the case, the Toronto Maple Leafs were looking to upgrade their blue line through free agency in the summer of 2008. In order to address their need, the Maple Leafs signed Jeff Finger to a four-year contract worth $14 million.

Jeff Finger Toronto Maple Leafs
Jeff Finger came as an inexperienced defender to the Maple Leafs (Photo by Dave Sandford/Getty Images)

Having only played one full season in the NHL before signing with the Maple Leafs, it is a wonder as to why Toronto offered $3.5 million per season to a player who had yet to prove his place in the NHL. Finger had spent two seasons with the Avalanche, playing 22 games in 2006-07 and 71 games in 2007-08. In those 93 career NHL games, Finger had only scored 24 points but was becoming known league-wide for his strong defensive play.

When the 2008-09 season finally began, the Maple Leafs were hoping Finger would be a strong defensive defenseman. In 66 games, Finger set his NHL career high with 23 points, yet failed to live up to the hype in terms of his strong play in the defensive end. That found Finger watching the games from the press box on more than a few occasions. In his second season, Finger effectively played himself out of the lineup. His poor play limited him to 39 games with Leafs, in which he contributed 10 points.

Eventually, the Leafs chose to waive Finger, sending him to the minors where he played parts of two seasons with the Toronto Marlies. In those two seasons, Finger played 23 and 31 games, the last of his professional hockey career.

David Clarkson, Toronto Maple Leafs

After spending the first seven seasons of his NHL career with the New Jersey Devils, David Clarkson was hitting the free agent market for the first time. The Maple Leafs “won” the sweepstakes, signing the winger to a seven-year, $36.75 million deal.

With the Devils, Clarkson was an average player, if that. In 426 games with the club, he had 97 goals, 170 points and 770 penalty minutes. He did look good in the Devils’ playoff run in 2011-12, where they reached the Stanley Cup Final before falling to the Los Angeles Kings. Clarkson had three goals and 12 points in the 24 games played and was a plus-eight.

David Clarkson (photo: Amy Irvin)

There was a lot of pressure on the newcomer, especially coming into the hockey hotbed of Toronto. He was being labelled as the next Wendel Clark, and as even a fan of him and the Leafs as a kid. Clarkson didn’t fill that role. In 118 games as a Maple Leaf, he had 26 points and a minus-25 rating to go along with his 185 penalty minutes.

Right off the bat, Clarkson got off to a terrible start in Toronto. In his first preseason with the team, he jumped over the boards to get involved in a fight, resulting in an automatic 10-game suspension. It was all downhill from there.

Related: Doomed from the Start: David Clarkson’s Time in Toronto

After just a season and a half with the Maple Leafs, he was brilliantly flipped by the new general manager at the time, Lou Lamoriello, to the Columbus Blue Jackets in exchange for the injured Nathan Horton, who just sits on the team’s long-term injured reserve list.

The Clarkson era in Toronto brought a lot of hope to the city’s fans and the organization itself, but it all came crashing down rather quickly.

Sheldon Souray, Edmonton Oilers

In the 2007 offseason, the Edmonton Oilers went shopping for a star defenseman. They found their man in Sheldon Souray, signing him to a five-year contract worth $27 million.

Souray had spent the first nine seasons of his career between the New Jersey Devils and Montreal Canadiens and was coming off of a huge year with the Canadiens. He had scored 26 goals and 64 points in 81 games during the 2006-07 season, which he parlayed into a huge contract with the Oilers. Yet prior to his breakout season, Souray had played average hockey and was highly injury prone, missing significant portions of time, including the entire 2002-03 season.

Sheldon Souray (THW Archives)

In his first season with the Oilers, Souray was slated to make $6.25 million. However, similar to the majority of his career to that point, the Edmonton native was once again hampered by injuries. Sheldon ended up playing in only 26 games with the Oilers in the 2007-08 season, in which he only scored three goals and 10 points. Souray’s second season was his only successful campaign with the Oilers, in which he managed to play 81 games, scoring 23 goals, 53 points and was named an All-Star. It was the only season in which the Oilers got what they had paid for.

The following 2009-10 season witnessed much of the same from Souray, who once again battled a multitude of injuries. Due to an early concussion followed by a hand injury which later became infected, Souray was only able to play in 37 games. In his third season with the Oilers, Souray scored a mere 13 points and had a disastrous minus-19 rating, emphasizing the chronic frustration which characterized Souray’s time in Edmonton.

Prior to the 2010-11 season, Souray demanded a trade from the Oilers, but due to his high cap hit and inability to stay healthy, no teams were interested in his services. Unable to trade Souray, the Oilers eventually put Sheldon on waivers before he was loaned to the Hershey Bears of the AHL. Souray finished the year with the Bears before the Oilers finally bought out his contract in the summer of 2011, forced to pay Souray $3 million over two years to not play on their team.

Wade Redden, New York Rangers

When the 2008 free agency period began, the New York Rangers wasted no time in signing Wade Redden to a six-year contract, worth $39 million.

Wade Redden New York Rangers
Wade Redden didn’t bring the game he had in Ottawa to the Rangers. (Photo by Jim McIsaac/Getty Images)

Redden had become known as one of the better defensemen in the NHL, and as a result was a highly sought after player by many teams. Wade had played all previous 11 years of his NHL career with the Ottawa Senators, with which he was a force both offensively and defensively. On top of a strong game in his own end, Redden was a consistent contributor, scoring 101 goals and 410 points in his 838 games with the Senators.

In Redden’s first season with the Rangers, he had an average year to his standard, scoring 26 points in 81 games, his lowest point total in the past ten years of his career. In 2009-10, his second season, Redden saw a continued regression in his game, producing two goals and 14 points over 75 games. By this point, Rangers fans had become vastly irritated with Redden, as his play was nowhere near worth the $8 million he was paid in each of his first two seasons.

The following season, Redden was waived and played each of the next two seasons with the Connecticut Whale of the AHL. The decision allowed the Rangers to remove the burden of Redden’s salary off of their salary cap.

In 2012-13, Redden had his contract bought out by the Rangers. New York elected to pay Wade upwards of $3 million over a three year period for him to not play within their organization. In 2012-13 he played 23 games with the St. Louis Blues and was traded to the Boston Bruins to play another six, collecting seven points total is what turned out to be his last season.

Brad Richards, New York Rangers

In 2011, the Rangers made what turned out to be yet another terrible free-agent signing, securing the services of Brad Richards for nine years, at a cost of $60 million.

Richards, who entered free agency following a five year, $39 million contract with the Dallas Stars, was the most sought after player available in 2011 free agency. A proven number one center, Richards attracted league-wide interest before deciding to sign the Rangers.

In years prior, Richards had been a consistent player offensively. With the Tampa Bay Lightning, Richards scored 489 points in 552 games, alongside winning the Lady Byng Trophy, Conn Smythe Trophy and the Stanley Cup, all in 2003-04. With Dallas, Richards’ game continued to improve, scoring over a point per game with 227 points in 220 contests. Yet everything changed for Richards in his first season in the big apple.

New York Rangers Roadtrip
Brad Richards (Rich Kane/Icon SMI)

Earning a whopping $12 million salary, which included a $10 million signing bonus, Richards had an average season, one which was poor compared to his standards. Scoring 25 goals in 2011-12, Richards totalled 66 points, his lowest total in a full season since his sophomore year the Lightning. Richards’ second season with the Rangers was even less impressive, as Brad was limited to 34 points over 46 games in a lockout-shortened campaign. Although his points per game were up slightly, his 11 goals were less than impressive.

In 2013-14, Richards’ third season with the Rangers, the situation got even worse. Brad was only able to score 20 goals, his lowest goal total in a full season in the past 10 years. The 51 points he scored were the lowest full-season total of his career, which certainly did not warrant a $9 million salary.

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After being demoted to the team’s fourth line in the playoffs and rumours swirling that he would be made a healthy scratch, Richards was bought out by the Rangers at the end of the 2013-14 season.

The decision to buy out Richards meant that he would remain on the Rangers’ books for the next 12 seasons, until the year 2025-26. During this immense stretch of time, Richards is owed an unimaginable $20.6 million to not play for the Rangers.

Brad Richards’ contract will certainly go down in history as one of the worst free-agent signings of all time.

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70 thoughts on “The Worst Free Agent Signings in NHL History”

  1. Atleast Nash and St.Louis haven’t bombed in NY :) And the Gomez signing was bad. I mean REALLY bad. But i still haven’t figured out how Sather got Gomez traded to the Canadiens for McDonagh :D

  2. Do you ever stop to wonder that several of those Rangers “horrible” players played under Torts? After watching the circus in Vancouver last year, I suspect I know why they tanked in NYC.

  3. The Rangers picking up Alexander Frolov on a 1 year, 3 million dollar contract was rough. 43 games played. 7 goals and 16 points… Not worth the 3 mil. The Rangers try to pay like the Yankees but it just hasn’t ever worked out for them. Players for hire may work in Baseball, but not in Hockey.

  4. Detroit, Stephen Weiss, Mikael Sammuleson, Jordin Tootoo, Uwe Krupp, Darien Hatcher. AndKen Holland is considered a top GM??

    • None of them were signed to ridiculous contracts. Why not mention the great signings Holland has made. People who know hockey have high opinions of Holland, but you know better.

  5. The Canucks signing of Mark Messier should be on this list. As much as he is revered by Ranger fans (which is probably why it isn’t on the list?) he is absolutely despised by Canuck fans. He might as well have literally slapped each of us in the face and he still wouldn’t be hated nearly as much.

  6. Worse series of events? While not a FA signing… about the pens trade Markus Naslund for alek stojanov. Stojanov tallied 7 points in 3 nhl seasons along with 209 penalty minutes. Naslund? Could have played with Lemieux but “wasn’t big enough”…….tallied 395 goals and 869 points over 1,117 games played.

    nice one.

  7. The Brad Richards signing wasn’t nearly one of the worst ever. The Rangers won 6 playoff series in three years with Richards and the only reason he was bought out was because the new CBA created cap re-capture rules which made keeping a front loaded contract on the books like his impossible to keep.

  8. Brad Richards signing worse than Ville Leino? NOT! John Scott outscored this bozo last year. The ONLY goal he scored last year was in a Shootout. This guy was signed to score goals. He took the money and took almost every game off.
    Now he tolls for the KHL as not one NHL team would sign him. They likely could have done so cheap, seeing as he got a buyout in Buffalo that is still paying him. That says something. From what I saw and heard, it seems as if he showed ZERO leadership ability on the team.

  9. The Jagr deal was not that bad. Jagr led the caps in scoring all three seasons if i’m not mistaken.. The players around him did nothing but lay eggs out on the ice. Ironically he gets traded to the Rangers and scores 54 goals to break the all time Ranger record lol..

  10. Two Eastern Conference Final appearances and a Stanley Cup appearance during Richards tenure. In addition, his cap hit was only $6.6M a far cry from the $9M listed. Every big free agent has signing bonuses added in, so lets be fair and just use the cap hit. The buy out is steep, but doesn’t cost the Rangers cap space and for a team as rich as them, they can afford it based on what he brought to the team.

    In addition, he averaged 0.72 points per game with NYR. Not exactly the worst thing in the world, and based on the list you have an inherent bias against the Rangers. Holik is one thing, Redden is another, but to have Richards and not Yashin or DiPietro is hilarious.

    Also, Gomez was dealt for McDonagh and the cap savings landed the Rangers Gaborik. If you are going to do this, at least apply some more thought for fairness.

  11. How could there be worse than Ville Leino by the Buffalo Sabres? $27 million and scored ZERO goals for the entire season!! He’s now playing in Russia and the Sabres are still paying him $1 million per year!

  12. Steven Weiss by Ken Holland of the Red Wings. He seems to like riding the bench for something near 5M.
    It’s becoming apparent the guy has no pride.

  13. “Kovalchuk agreed to a 17-year, $102 million deal to remain with the Devils”
    By far the worst contract in NHL history

    • Kovalchuk lead the league among active players in goals scored at the time of his signing. For the devils, a team with goal scoring troubles at the time, going after Kovalchuk was a no brainer. They returned to the cup finals within only 2 seasons of his signing and falling just short after a comeback in a 6 game series. This is obviously an angry rangers fanboy upset over all their bad signings on this list. It happens, and still they managed to somehow get to the finals last year for 5 games (credit Lundqvist). Back to Kovalchuk though. Obviously after the lockout and playing in the KHL in his home country, he did not return. However how can anyone really blame the guy for leaving…his two experiences in the U.S. were in Atlanta, GA and Newark, NJ.

  14. Nathan Horton is in the midst of one right now. He was signed to a 37 million contract while awaiting surgery and has yet to play this season and may have retire to a degenerative back issue with his spine! Nice work by the team docs on that one boys!

  15. Ville Friggin’ Leino got paid 2.7 million for each goal he scored in a Sabres uniform. I’m not sure how much worse a free agent signing could get.

    • Dan Cloutier was acquired from Vancouver for two 2nd round picks & signed for 3 years/ 9 mil before playing his first game with the Kings. He played a total of 33 bad games.

  16. @Gary Read the subject of the article. It is Worst FREE AGENT signings. Not worst contracts. DiPietro would be top 3 easy if that was the article.

  17. Gomez landed NY Mcdonagh and Higgins.,…..You can scratch that one off!!! I hope Sather lands 10 more Gomez’s ….If the return is anywhere near a Mcdonagh!

  18. Lets see, Mike Rathje played 1 season before getting hurt and never played again for the Flyers after signing a huge contract. Speaking of huge, Bryzgalov was a HUGE mistake with a 9 year.51 million deal. Andrew Macdonald contract will soon be added to this list. Vinny contract is quite terrible as well.

  19. Scott Gomez Rangers singing should’ve made the list and Brad Richards should not. The rules changed after Richards signed his contract with hard CAP and recapture rules.

  20. Rick DiPietro’s 15 year contract with the New York Islanders has to be one of, if not the worst contracts in NHL history.

  21. if you think Brad Richards contract was worse than Gomez or Drury for the Rangers you must live in a cave. He did help lead the team to the Eastern Conference Finals and the Stanley Cup Finals. Am I glad we were able to shed his contract, yes, did he look sluggish at the end of both playoff runs, yes he did, but it’s not like he scored 5 goals. Gomez signing was best for bring us our new Captain in a trade. Drury was a total bust. At least Richards provided leadership, was 3rd on the team in goals his first season and 2nd in goals last season. Give the guy a little credit, his playoff goal in the closing seconds vs Washington changed that series. Do you remember who had the game-winning goal in game 7 against Pittsburgh last year, the series we were down 3-1? Yep, Brad Richards. Calling his contract one of the biggest busts is insane.

  22. Facts on Brad Richards are wrong. In the 2013-2014 season he was a good player just not worth the money. It was the 2012-2013 season where he was god awful, scratched, and Sather gave him one more chance. Also Scott Gomez is the worst contract of all time.

  23. Buffalo threw stupid money at Ville Leino, after having a halfway decent season in Philly, only to ask him to move from wing to center, and watched his performance tank. 29G, 36A in 137 games for $27M.

  24. Sabres buy out Leino contract: report

    Buffalo Sabres forward Ville Leino cleared waivers Wednesday and the team has used one of their two compliance buyouts on him, according to multiple reports.

    Leino, 30, had three years remaining on a six-year, $27 million contract he signed prior to the 2011-12 season. The annual average value of the remaining contract is $4.5 million per season.

    Leino signed the contract after he set career highs with 19 goals and 53 points for the Philadelphia Flyers in 2011-12. He did not have a goal in 58 games this season and had 15 assists. Leino has 10 goals and 46 points in 137 games with the Sabres.

    “Free agency starts first of July, and we’ll go from there,” Leino’s agent, Markus Lehto, told the Buffalo News, adding Leino was not surprised by the buyout. “His priority is to play in the NHL. He knows he’s a very good NHL player. Obviously, the past two seasons have been just average, I would say, but I’m not going to go and try and analyze what happened. I mean, we’ll just look forward.”

    The window for teams to offer a compliance buyout to players opened Monday. Under the Collective Bargaining Agreement, teams were given two special buyout provisions to be used after the 2012-13 and 2013-14 seasons that allow them to buy out a player’s contract while not having it count toward the salary cap. This would be the first compliance buyout used by the Sabres.

    Teams have until 5 p.m. ET on June 30 to decide to use a compliance buyout.

  25. Brad Richards wasn’t that bad. A bit much for what his output was? Sure, but guys at the top of the UFA heap generally get overpaid. And yes, his 2nd year in NY was god awful. But the only reason he was bought out was because the NHL closed a cap-circumvention loophole and, in doing so, retroactively changed the terms of his contract. If that doesn’t happen, Brad Richards is still a Ranger.

  26. The Flyers signing Peter Forsberg. A nice idea at the time, but his groin injuries, caused by a deformed foot, created a lot of controversy and limited the amount of time he actually played for the Flyers.

    • Na, he still produced and fetched them Kimmo Timonen and Scott Hartnell. Obviously, others included like Upshall and, at the time the best defensive prospect, Ryan Parent. They didnt work out, however Kimo ( still on the team ) and Hartnell ( first year not on the team ) were great.

      • Don’t quite have your facts correct. Paul Holmgren traded for the negotiating rights for both Hartnell and Timonen after the 2006-2007 season. Neither of those players were part of the Peter Forsberg trade. Scottie Upshall, Ryan Parent and 1st and 3rd round draft picks were traded to the Flyers for Forsberg.

  27. What about Washington’s signing of Jaromir Jagr? $77M over 7 years… That was abysmal! As was his explanation (after he was traded to the Rangers) of why he was so bad in DC…

    • Jagr led the team in scoring all three seasons in DC if i’m not mistaken.. The players around him did nothing but lay eggs out on the ice. Ironically he goes to the Rangers and breaks the all time Rangers goals record with 54..

  28. How can you list Jeff Finger without mentioning that the Leafs signed him because they thought he was someone else?

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