NHL free agency provides general managers with the ideal opportunity to improve the franchise. Instead of having to sacrifice top talent in a trade, teams can sign a player – only at the expense of big money. This can lead to a sudden turn around of a franchise or it could spell financial ruin for whatever the term of their huge contract blunder may be.
But over the past decade, every NHL team has struck out on at least one massive free agent signing. Budget-conscious teams like the Carolina Hurricanes, Arizona Coyotes and Winnipeg Jets have stayed away from handing out mega deals, but they still got burned on a number of free agent signings that just didn’t pan out the way they thought they would.
Teams like the Philadelphia Flyers and New York Rangers have set the standard for being terrible at managing their money. These teams have signed a number of big-named players, only to suffer eggs on their faces. One would imagine that after the first five major mistakes they made that they would learn, but they continue to make the same ridiculous signings to aging veterans with health issues.
Teams should go through these 31 awful free agent signings, and try to learn from them. Here is every NHL team’s worst free agent pickup in the last decade.
31. Anaheim Ducks: Sheldon Souray
For the most part, the Anaheim Ducks have been largely successful in free agency. Signing Teemu Selanne and Scott Niedermayer helped them win their first Stanley Cup in 2007, and they’ve avoided disaster contracts for the most part. But in the 2012 offseason, the Ducks took a chance on ageing and injury-prone defenceman Sheldon Souray – signing the former All-Star to a three-year contract worth $11 million. He scored seven goals and 17 points in the lockout-shortened 48-game season, and helped Anaheim win the Pacific Division.
But Souray suffered shoulder and wrist injuries, and sat out the entire 2013-14 season. In the summer of 2015, Souray formally announced his retirement, and the Ducks were burned with a pretty bad contract signing. At least it was at a low term, and didn’t cost too much money.
30. Arizona Coyotes: Mike Ribeiro
The Arizona Coyotes franchise has generally stayed away from handing out big contracts. They sure as heck chose a bad time to give out a lucrative deal when the team signed Mike Ribeiro to a four-year deal worth $22 million. Ribeiro was coming off 49-point season for the Washington Capitals in the 48-game regular season, so the deal looked smart for Arizona at the time.
But Ribeiro was dealing with personal struggles, and posted a disappointing 16 goals an 47 points. Ribeiro was bought out after his first and only year in The Desert. Management wasn’t happy with his apparent drinking issues off the ice. Ribeiro later admitted that he struggled with the Coyotes as he tried to repair his broken marriage. He later joined the Nashville Predators and briefly revived his career. Ribeiro has since retired.
29. Boston Bruins: Matt Beleskey
The Bruins have built the core of their team through great drafting (Patrice Bergeron, Brad Marchand, David Pastrnak, Tuukka Rask and Charlie McAvoy). But when it’s come to signing free agents, the Bruins have been burned more often than not. After scoring 22 goals and 32 points with the Anaheim Ducks in 2014-15, the Bruins gave Beleskey a five-year deal worth $19.8 million. A lot of money for a player who had one good season, and the Bruins have since regretted it.
Beleskey scored just 15 goals and 37 points in his first year with Boston, then missed half of 2016-17 due to injuries – scoring just eight points. Beleskey has appeared in just 14 games for Boston this year, tallying zero points. He’s spent the bulk of the 2017-18 season with their AHL affiliate, the Providence Bruins.
28. Buffalo Sabres: Christian Ehrhoff
This was a toss-up between Ehrhoff and Ville Leino. But the former cost he Sabres more money and term, so he gets the dishonour here. With new owner Terry Pegula on board, the Sabres were given the green light to spend more money. So they signed Christian Ehrhoff to a 10-year contract worth $40 million. Ehrhoff had scored 14 goals in each of his two seasons with the Canucks, surpassing the 40-point mark each time. The Sabres thought they had a legitimate top-pairing blueliner, but they could not be more wrong.
Ehrhoff lasted just three seasons in Buffalo, and never topped 33 points in a season there. Furthermore, the Sabres never made the playoffs once with Ehrhoff. The Sabres then bough him out during the 2014 offseason.
27. Calgary Flames: Dennis Wideman
Despite missing the playoffs for a third consecutive year in 2012, the Calgary Flames opted to pass on an inevitable rebuild and signed veteran blueliner Dennis Wideman to a five-year contract worth $26.25 million. Wideman didn’t do much to help the Flames get better, however. Coming off a 46-point season with the Washington Capitals, he contributed just 22 and 21 points in 2012-13 and 2013-14, respectively. Wideman had a strong 2014-15 campaign by scoring 56 points, but it was all downhill from there.
Wideman missed 31 games in 2015-16, and was suspended for hitting referee Don Henderson from behind. The following year was Wideman’s last in the NHL, and he tallied just 18 points in 57 games. He then retired and became an assistan coach for the Kitchener Rangers of the OHL.
26. Carolina Hurricanes: Joni Pitkanen
The Hurricanes have been able to stay away from horrible free agent signings. But whenever they hand out a bad contract, it tends to be an extension for one of their players. Just look at Jordan Staal, Cam Ward and Alexander Semin, among others.
But Carolina made one forgettable signing in the 2008 offseason, inking blueliner Joni Pitkanen to a three-year contract worth $12 million. Pikanen looked to rebound after a disappointing stint with the Edmonton Oilers, having posted a least 43 points in two seasons with the Philadelphia Flyers before. Pitkanen cracked the 40-point mark once in Carolina, but was otherwise an overpaid and unreliable player. Carolina made the playoffs just once with Pitkanen, making his contract even worse. Pitkanen last played for Carolina in 2013, and later joined Oulun Karpat in the Finnish Liiga.
25. Chicago Blackhawks: Cristobal Huet
Even though the Chicago Blackhawks owned a top goalie in Nikolai Khabibulin, they didn’t feel secure enough in goal. So they went out and signed French goalie Cristobal Huet to a four-year deal worth $22.4 million in the 2008 offseason. Predictably, the Blackhawks rolled with Khabibulin throughout the season, and Huet only started when the ‘Bhulin Wall’ went down with injuries. He posted a solid 20-15-4 record, but had a mere 2.53 goals against average and .909 save percentage.
The Blackhawks then let Khabibulin walk in the 2009 offseason, and rolled with Huet to start the following season. However, Antti Niemi stole the job from Huet and led he Blackhawks to their first Stanley Cup championship in 49 years. Huet was then sent to a team in Switzerland, and never played in the NHL again.
24. Colorado Avalanche: Carl Soderberg
After passing the 40-point mark twice with the Boston Bruins, Carl Soderberg made some bank via the Colorado Avalanche. Unable to reach a new contract with Boston, Soderberg signed a five-year contract worth $23.75 million in the 2015 offseason. Given his age (30), and the fact he only played two seasons in the NHL, the contract was a big risk for the Avalanche.
Soderberg posted a respectable 12 goals and 50 points in his first season with Colorado. But in his second season there, Soderberg tallied a woeful six goals and 14 points in 80 games. Mind you, that was a horrible season for all the players in Colorado. In 2017-18, the 32-year-old Soderberg is on pace for 18 goals and 42 points. That’s not terrible by any means, but it’s not exactly great. Given his age and inconsistent play, this will be a bad contract over the next couple of years.
23. Columbus Blue Jackets: Nathan Horton
In his prime, Nathan Horton was one of hockey’s premier power forwards. When healthy, he was a sure bet to post 20-goal and 50-point seasons, but he was never the same after suffering an ugly hit from Aaron Rome during the 2011 Stanley Cup Final. Horton played in just 89 games over the 2011-12 and 2012-13 seasons, but was among the top free agents heading into the 2013 offseason. The budget-conscious Columbus Blue Jackets opted to break the bank, and signed Horton to a whopping seven-year contract worth $37.1 million.
A back injury limited Horton to just 36 games in Columbus, where he tallied 19 points. Horton was then flipped to the Toronto Maple Leafs in 2015 for David Clarkson. Though he hasn’t formally retired, his back injury has all but ended Horton’s career. Columbus is very fortunate they were able to escape this contract.
22. Dallas Stars: Antti Niemi
Niemi won a Stanley Cup in his rookie season with the Chicago Blackhawks in 2010. He then followed it up with five strong seasons with the San Jose Sharks, where he won 30-plus games four times. The Finnish netminder then hit free agency in 2015. Despite the Dallas Stars already owning a quality No. 1 in Kari Lehtonen, the Stars gave Niemi a three-year contract worth $13.5 million. He and Lehtonen shared the net throughout the season, but the former was by far the better goalie.
Niemi had a solid 25-13-7 record, but a terrible 2.67 goals against average and .905 save percentage. Niemi posted a horrible .865 save percentage in the playoffs, and the Central Division-winning Stars were eliminated in the second round. The Stars placed Niemi on waivers after the 2016-17 season and bought out the final year of his contract.
21. Detroit Red Wings: Stephen Weiss
After nearly a decade of being heralded as the best GM in all of hockey, Ken Holland has seen his reputation take a hit. He’s handed out an awful amount of bad contracts – to his own players and to newcomers. But none were bigger wastes of money than Stephen Weiss – who received a five-year contract worth $24.5 million in 2013.
Weiss was supposed to slot in as a reliable top-six forward, having developed as a reliable 20-goal and 40-50 point player. But his tenure in the Motor City was a complete disaster, to say the least. Injuries limited Weiss to just 26 games in the 2013-14 season, and he posted just four points. The following year, Weiss scored just 25 points in 52 games. The Red Wings bought out his contract, ridding themselves of the worst deal handed out by Holland in the past decade.
20. Edmonton Oilers: Nikolai Khabibulin
After barely missing out on the playoffs in 2009, the Edmonton Oilers desperately looked for a new starting goalie. They signed former Stanley Cup champion netminder Nikolai Khabibulin to a four-year contract worth $15 million. This was despite a lacklustre four-year tenure in Chicago, and the fact he had just turned 36 years of age.
‘The Bhulin Wall’ struggled in his four years with the Oilers, who finished dead last in two of his four seasons there. Khabibulin never topped 12 wins in a season with Edmonton. He posted a total record of 33-67-14 with the Oilers, along with a .903 save percentage and woeful 3.00 goals against average. On the bright side, Khabibulin’s terrible play helped the Oilers net the first-overall pick in 2010, 2011 and 2012. That’s something to celebrate, right?
19. Florida Panthers: Dave Bolland
Dave Bolland was an integral piece of the Chicago Blackhawks’ Stanley Cup championships in 2010 and 2013 – scoring the Cup-clinching goal in the latter year. But salary cap constraints forced the ‘Hawks to reluctantly deal away Bolland to the Toronto Maple Leafs in the 2013 off-season. Bolland put up a solid 12 points in 23 games for Toronto during the 2013-14 season, but injuries piled up and forced him to miss the remainder of the campaign. Despite injury concerns, the Panthers signed Bolland to a massive five-year contract worth $27.5 million.
Over the next two years, Bolland only played a total of 78 games in the Sunshine State, scoring seven goals and 28 points. The Panthers dealt him away to the Coyotes in 2016, but Bolland’s agent said he’s unlikely to play hockey again with ankle and back injuries.
18. Los Angeles Kings: Simon Gagne
The Kings are one of the worst teams when it comes to extending their players. Marian Gaborik, Dustin Brown, Anze Kopitar and Jonathan Quick are among the players on this team that carry expensive-long term contracts as they enter their twilight years. But when it’s come to adding new players in free agency, the Kings haven’t been all that bad. However, the Simon Gagne signing (two years, $7 million in 2011), wasn’t one of the smarter decision by former GM, Dean Lombardi.
Gagne was well past his playing prime, and had battled a series of injuries over the past five years. He scored just 17 points in 34 games for the Kings in 2011-12, though they did manage to win the Stanley Cup. Gagne had just five points in 11 games the following season, and was traded back to the Philadelphia Flyers.
17. Minnesota Wild: Zach Parise
After missing the playoffs for the fourth-straight year, the Minnesota Wild signed defenceman Ryan Suter and sniper Zach Parise to matching 13-year contracts worth $99 million each. The former has been a Norris-caliber defenceman, and the workhorse Suter has turned the Wild into a perennial playoff team.
The same cannot be said about Parise, presently speaking. Though he scored at least 20 goals and 50 points in three of his first four years with the Wild, Parise’s play has massively declined. He missed 13 games last season, scoring just 19 goals and 42 points. Injuries have limited Parise to nine games in 2017-18, and he only has three points. He’s 34 years of age this offseason, and simply hasn’t have the time nor health to regain his old touch. It’s safe to say this contract is going to hurt the Wild for a long time.
16. Montreal Canadiens: Mike Cammalleri
After a disappointing first-round exit to the Boston Bruins in the opening round of the 2009 playoffs, the Montreal Canadiens decided to make some changes. They let fan favorites Saku Koivu and Alexei Kovalev walk in free agency, and signed veteran snipers Brian Gionta and Mike Cammalleri in the offseason. Gionta’s contract was money well spent, but the same can’t be said about Cammalleri.
Cammalleri joined the Habs on a five-year contract worth a total of $30 million. Cammalleri scored 26 goals and 50 points in his first season, but slipped to 19 goals and 47 points the next. During a nightmare 2011-12 season for the Habs, Cammalleri called out the team and referred to them as “losers.” The Habs then traded him to the Calgary Flames, and they got themselves out of a brutal contract.
15. Nashville Predators: Nick Bonino
It’s amazing. David Poile is easily the best GM in the NHL today, because he has gotten away with avoiding horrible contracts for the most part. Most of his money has been spent on keeping the top players that he drafted and/or traded for, including Shea Weber, Kyle Turris, Ryan Johansen, Pekka Rinne and others.
Over the past 10 years, Poile has avoided the toxic contract problems. However, 2017 pickup Nick Bonino is looking like a massive flop. After seeing the veteran lead the Pittsburgh Penguins to a second-straight Stanley Cup over his Preds in 2017, Poile signed Bonino to a four-year contract worth $16.4 million. Bonino hasn’t been the third-line centre Nashville hoped for. He’s on pace to finish with just 15 goals and 25 points. Consider this a rare blemish on Poile’s otherwise impressive resume.
14. New Jersey Devils: Anton Volchenkov
Volchenkov was among the NHL’s premier shutdown defencemen and consistent leaders in blocked shots. But he priced himself out of the Ottawa Senators budget, and signed with the New Jersey Devils for six years worth $25.5 million in the summer of 2010. Volchenkov was joining a New Jersey team that was coming off a second-place finish in the Eastern Conference, extended Ilya Kovalchuk long-term and had a world class goalie in Martin Brodeur. Volchenkov was supposed to be the final piece in the team’s championship quest.
But Volchenkov became a disappointment in New Jersey. He wasn’t even close to being the reliable shutdown defender, and often looked lost in the Devils’ neutral zone trap schemes. New Jersey did reach the Stanley Cup Final in 2012, but Volchenkov didn’t do much to contribute. He was later bought out and last played for the Nashville Predators in 2014-15.
13. New York Islanders: Andrew Ladd
After winning their first playoff series in 23 years, the New York Islanders were looking to add one more piece to compete for a Stanley Cup. So in the 2016 offseason, they signed former Winnipeg Jets captain Andrew Ladd to a seven-year contract worth $38.5 million. We aren’t even two years into the deal, but it’s already looking ugly.
Ladd finished 2016-17 with 23 goals and just 31 points – his lowest points total in nine years. Ladd was previously a consistent 20-goal, 50-60 point player. But given his age (32), and physical two-way style, Ladd has nowhere to go but down from here on out. He’s on pace to finish the season 16 goals and 32 points. That does not warrant five more years of this contract. Ladd hasn’t been able to fit with the Islanders, and they may want to consider buying him out in the next couple of years.
12. New York Rangers: Wade Redden
Gosh, we could write a novel about horrible contracts handed out by the New York Rangers over the years. Scott Gomez, Chris Drury and Brad Richards stand out, but none were worse than the Wade Redden signing in 2008. That year, the Blueshirts handed him to a six-year pact worth $39 million. Redden was previously the backbone of the Ottawa Senators blue line for a decade, helping them reach the Stanley Cup Final in 2007. A well-respected veteran with strong two-way play, Redden was supposed to bring a ton to the Rangers in their championship quest. Long story short: He did the opposite.
Redden’s first year with the Rangers was quite porous, as he tallied just three goals and 26 points while struggling in his own zone. Following a terrible 14-point campaign in 2009-10, the Rangers buried his contract in the minors – and bought out Redden in 2013. So ended the worst contract in franchise history.
11. Ottawa Senators: Sergei Gonchar
After losing top-pairing defenseman Anton Volchenkov in free agency, the Ottawa Senators quickly looked to fill the void. So they signed veteran standout Sergei Gonchar to a three-year contract worth $16 million. He was coming off an 11-goal and 50-point season with the Pittsburgh Penguins, so the deal looked like a bargain more than anything else.
Unfortunately for the Senators, Gonchar was nearing the end of his prime when they signed him. He posted a mere 27 points in his first season with the Senators, then tallied a mere 37 the following year. Gonchar would post a respectable 27 points in 45 games during the lockout-shortened 48-game season in 2012-13. But he took up too much cap space and was a major disapoinment in his first two seasons in the nation’s capital. Ottawa picked a bad time to hand out a big contract to a fading vet.
10. Philadelphia Flyers: Ilya Bryzgalov
How desperate were the Flyers for a legitimate No. 1 goalie? GM Paul Holmgren willingly shipped away franchise stars Mike Richards and Jeff Carter, ensuring that he had the cap space to sign veteran Ilya Bryzgalov to a nine-year contract worth $51 million in 2011. Bryzgalov had registered at least 26 wins in the previous four seasons, so the deal looked smart at first.
But Bryzgalov flopped in the City of Brotherly Love. He would last just two seasons in Philly, posting a total record of 52-33-10 with a woeful .905 save percentage and mere 2.60 goals against average. After just two years, the Flyers used a compliance buyout on Bryzgalov, getting out of his miserable contract that is by far the worst in franchise history.
9. Pittsburgh Penguins: Rob Scuderi
Scuderi never brought much offence, but he was an ideal shutdown defenceman that helped the Pittsburgh Penguins win the Stanley Cup in 2009. Scuderi was a physical player and could play against the opposition’s top line. After winning a Cup in Pittsburgh, Scuderi spent four productive seasons with the Los Angeles Kings – winning another championship with them in 2012. A year later, he returned to the Steel City on a four-year contract worth $13.5 million.
But Scuderi struggled to play like his old self in Pittsburgh, and was a major liability on defence. During the 2015-16 season, he was traded to the Chicago Blackhawks in exchange for Trevor Daley. The latter was a key piece of Pittsburgh’s 2016 and 2017 Stanley Cup championships, so at least they got out of Scuderi’s brutal contract in a fashionable way.
8. San Jose Sharks: Mikkel Boedker
The San Jose Sharks reached the Stanley Cup Final for the first time ever in 2016. However, they were notoriously outplayed and out-skated by a much faster Pittsburgh Penguins team that dispatched them in six games. Head coach Pete DeBoer noted the Pens’ superior speed, and knew his team had to add some wheels to get to the next level.
So they signed speedy forward Mikkel Boedker to a four-year deal worth $16 million, hoping he’d be the final piece of a championship puzzle. But Boedker struggled in his first season with the Sharks, scoring just 10 goals and 26 points. At this point of the season, he’s not going to come anywhere close to the 20-goal and 40-point form the Sharks had hoped when they signed him. The term wasn’t long, but Boedker is wasting ample cap space on a team that must re-sign or replace Joe Thornton this offseason.
7. St. Louis Blues: Paul Stastny
After coming up short in the playoffs over and over again, the St. Louis Blues decided it was time for a big move. They signed perennial Colorado Avalanche star Paul Stastny to a four-year contract worth $28 million in 2014. Stastny was coming off a 25-goal, 60-point season with Colorado, so the deal seemed like a fair one for both sides.
But in the midst of the final year of his contract, Stastny hasn’t been worth the money in St. Louis. He hasn’t topped 49 points in his first three seasons with the Blues, nor has he reached the 20-goal mark. It’s unlikely Stastny reaches 20 goals or 50 points in 2017-18. Furthermore, the Blues have only advanced past the second round once with Stastny. He simply hasn’t done enough to earn $7 million a season, but the Blues are lucky that they’ll have him off the books this offseason.
6. Tampa Bay Lightning: Matt Carle
A solid top-four defenseman with a pair of 40-point seasons under his belt, Matt Carle received a nice contract from the Tampa Bay Lightning in 2012. Carle returned to Tampa on a six-year deal worth $33 million, which was a lot of money and term for a guy who was never exactly a superstar.
Carle was never to regain his old form once he came back to Tampa, however. He never topped more than 31 points in a season, and was often a liability on defence. The Lightning did reach the Stanley Cup Final with Carle in 2015, but he did not play much of a factor. The Lightning bought out the final two years of Carle’s contract. He joined the Nashville Predators in 2016, but was bought out and later retired.
5. Toronto Maple Leafs: David Clarkson
Coming off their first postseason appearance in nine years, the Toronto Maple Leafs were looking to add that final piece for a shot at the Stanley Cup. So they went out and signed power forward David Clarkson, who was eager to join his hometown team. Clarkson received a seven-year contract worth $36.75 million even though his career high in points was 46.
Clarkson’s tenure in Toronto got off to a horrible start. He was suspended 10 games for leaving the bench to engage in a fight during a preseason game. Clarkson scored just five goals and 11 points in 60 games. The following year, he tallied just 10 goals and five assists. The Maple Leafs somehow got the Columbus Blue Jackets to take on his contract in exchange for Nathan Horton’s. Clarkson missed the entire 2016-17 season and was later traded to the Vegas Golden Knights. His NHL career is likely all but over now.
4. Vancouver Canucks: Loui Eriksson
This one’s a no-brainer. Despite an obvious need to rebuild after finishing third-last in the NHL in 2016, the Canucks were desperate to add a scorer. So GM Jim Benning signed Loui Eriksson to a six-year deal worth $36 million, hoping he could form some magic with fellow Swedes Daniel and Henrik Sedin. At first, the move looked geniues. Eriksson was one of the game’s more effective two-way players, reaching the 20-goal mark six times and the 60-point plateau five times. But Eriksson must regret signing away his future to Vancouver.
He had just 11 goals and 24 points in 65 games for the Canucks last year. He’s on pace to finish 2017-18 with 12 goals and 32 points. Did we mention he’s 32 years of age and is under contract for four more years? The Canucks may want to look at a buyout in the coming years.
3. Vegas Golden Knights: Vadim Shipachyov
A perennial star in the KHL for SKA Saint Petersburg, Vadim Shipachyov was one of the top free agents on the market in 2017. GM George McPhee worked his magic and signed Shipachyov during the playoffs. But Shipachyov clashed with management and refused to join their AHL team. Announcing his intentions to go back to Russia, the Golden Knights placed Shipachyov on waivers, before eventually tearing up his contract. Shipachyov would return to his KHL team, and the Golden Knights were left with eggs on their faces.
What hurts more is they weren’t able to even get a draft pick for him from another NHL team. Shipachyov had value, but Vegas was stuck left empty-handed. But at least it was only a one-year deal, so they won’t be feeling the long-term effects of the failed Shipachyov signing.
2. Washington Capitals: Brooks Orpik
When the Washington Capitals signed Brooks Orpik to a five-year contract worth $27.5 million in 2014, it felt like a double whammy move. Not only did the Capitals improve their blue line depth, but they weakened the rival Pittsburgh Penguins. Orpik was a backbone on the Penguins defence for a decade, shutting down the opposition’s top stars and helping them win the Stanley Cup back in 2009.
But Orpik hasn’t justified all the money in Washington. He’s been an inconsistent blueliner at best. To make matters worse, Orpik’s Capitals were eliminated by his old Penguins team in the 2016 and 2017 playoffs. Pittsburgh won the Stanley Cup both years. So much for the Capitals getting a reliable defenseman, and so much for weakening their arch enemies.
1. Winnipeg Jets: Olli Jokinen
Following their first season since returning to The Great White North from Atlanta, the Winnipeg Jets signed fading veteran Olli Jokinen to a two-year contract worth $9 million. Jokinen was entering his age-34 season, and was no longer the former superstar we saw with the Florida Panthers.
Jokinen tallied just seven goals and as many assists in 45 games with the Jets in 2012-13. The following year, he tallied 18 goals and 43 points, but the Jets once again finished near the bottom in the NHL standings. Jokinen was signed to bring in leadership and scoring depth for the Flames. But he didn’t do much of either, and the budget-conscious Jets didn’t receive all that much from the former Finnish standout. Easily their worst contract in the franchise’s young history.
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