Every NHL Team's Worst Free-Agent Signing of the Cap Era

Lyle Fitzsimmons@@fitzbitzFeatured ColumnistAugust 24, 2021

Every NHL Team's Worst Free-Agent Signing of the Cap Era

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    Sometimes, they're game-changers.

    When a team makes a bid for an unrestricted free agent and it works out, everyone's happy.

    Jerseys start selling. Wins start coming. And Stanley Cup parades seem possible.

    But when those free-agency gambles don't pay off...ouch.

    Losses pile up. Coaches get fired. And general managers start cleaning out desks, too.

    Each of the NHL's 31 veteran franchises has hit a home run in free agency since the salary cap was installed, and they've each made a faulty bet when it comes to a contract offer, too. In fact, even the soon-to-debut Seattle Kraken wound up with a head-scratcher or two when they dipped into the UFA pool this summer.

    This year's highest-profile UFA deal went to defenseman Dougie Hamilton, who took $63 million over seven seasons to ditch the Carolina Hurricanes for the New Jersey Devils.

    The B/R hockey writing types looked all the way back to 2005-06 to recall the biggest missteps each organization has made in the cap era—be it a player, a contract term or a total dollar value. Or in many cases, a combination of all three.

    Take a look at what we came up with and share a thought or two of your own in the comments.

Nos. 1-7: Ducks, Coyotes, Bruins, Sabres, Flames, Hurricanes, Blackhawks

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    Anaheim Ducks: Todd Bertuzzi (2007)

    The burly winger was a force over several seasons with the Vancouver Canucks, but the Ducks got the post-Steve Moore suspension version. Two years and $8 million wasn't a fortune, but he played just 68 games and scored 14 goals in 2007-08 before Anaheim bought out the deal halfway through. 


    Arizona Coyotes: Mike Ribeiro (2013)

    Given his status as a point-per-game player with the Washington Capitals, it's not surprising the Coyotes shelled out $22 million over four years for Ribeiro. But to say it didn't work out is an understatement. He slumped to 47 points in 80 games and was bought out after one season, with former general manager Don Maloney saying Ribeiro had "real behavioral issues" during his time with the franchise.


    Boston Bruins: David Backes (2016)

    Let the record show that Backes reached 30 goals twice and 20 goals four times during his time with the St. Louis Blues, which prompted the Bruins to lavish him with $30 million over five seasons. The production fizzled, however, and the Bruins dealt him to Anaheim after 39 goals in three-plus seasons.


    Buffalo Sabres: Ville Leino (2011)

    The summer of 2011 was a challenging one in Buffalo. Just a day after the Sabres dumped $40 million on Christian Ehrhoff, they doled out six years and $27 million to Leino, a 27-year-old winger with 30 NHL goals. Three years later, he'd added just 10 more to that total and was bought out of the deal's back half.


    Calgary Flames: Dennis Wideman (2012)

    Wideman was a serviceable enough defenseman who'd played parts of seven seasons with four NHL teams, but probably not worth the five years and $26.25 million he was offered by the Flames. He surpassed 22 points just once in the life of the contract and retired after the 2016-17 season.


    Carolina Hurricanes: Joni Pitkanen (2008, 2011)

    Pitkanen was one of the league's top young defensemen with the Philadelphia Flyers, and the Hurricanes looked to reinvigorate him after a lost season with the Edmonton Oilers. But the three-year, $12 million deal and three-year, $13.5 million extension look bad in retrospect after he reached 40 points just once.


    Chicago Blackhawks: Brent Seabrook (2016)

    It's good to win Stanley Cups. First, because they're fun. Second, because they help players get paid. Seabrook was one of those players, at age 30, who got an eight-year, $55 million contract in the afterglow of three titles. His performance—go figure—has fallen off, and Chicago shipped him out after the 2020-21 season.

Nos. 8-12: Avalanche, Blue Jackets, Stars, Red Wings, Oilers

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    Colorado Avalanche: Brad May (2005)

    Lots of things made this one ugly for the Avs. May wasn't at all a productive player in a Colorado uniform, but even worse, he'd been one of the triggers for the aforementioned Steve Moore incident while he played in Vancouver. He scored three goals in 64 games before a trade to Anaheim during the 2006-07 season.


    Columbus Blue Jackets: Nathan Horton (2013)

    After nine straight seasons with double-digit goals, including a peak output of 31, the Blue Jackets went all in on the 28-year-old power forward to the tune of seven years and $37.1 million. But the deal was a bust. Thanks to injuries, Horton played just 36 games and scored five goals before a trade to Toronto in 2015.


    Dallas Stars: Antti Niemi (2015)

    Niemi certainly arrived to the Lone Star State with plenty of goaltending street cred. He was a Cup champion in Chicago and a 30-plus game winner four times with San Jose before getting a three-year $13.5 million offer from the Stars. By the end of year two, though, he was a backup and got a buyout.


    Detroit Red Wings: Stephen Weiss (2013)

    It's easy to forget that Weiss was a pretty effective NHL center, scoring double-digit goals seven times and reaching 60 points twice with Florida. But the five-year, $24.5 million deal he got from the Red Wings was something Detroit fans wish they couldn't remember. He played 78 games in two years before a buyout.


    Edmonton Oilers: Sheldon Souray (2007)

    If only Souray could have been Chris Pronger. That's surely what the Oilers were still looking for when they inked the hulking Alberta native to a five-year, $27 million pact. Instead, they got one strong year, two injury-riddled years and a fourth year that saw him relegated to the AHL before a final-season buyout.

Nos. 13-17: Panthers, Kings, Wild, Canadiens, Predators

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    Florida Panthers: Dave Bolland (2014)

    Another ex-Blackhawk who won Stanley Cups and got paid. Bolland went from Chicago to Toronto, but struck it rich with the Panthers in 2014 when they ponied up $27.5 million over five seasons. He scored just six goals in the first season and one over 25 games in the second due to injuries. He hasn't played since.


    Los Angeles Kings: Simon Gagne (2011)

    Gagne was a productive winger with the Philadelphia Flyers, but he was already skidding when the Kings gave him two years and $7 million after he spent 2010-11 with Tampa Bay. He had 17 points with L.A. in 2011-12, then played just 11 games with the Kings the following season before a trade back to Philly.


    Minnesota Wild: Zach Parise/Ryan Suter (2012)

    You can't separate the matching 13-year, $99 million deals the Wild shelled out to both Parise and Suter in a July 4, 2012 spending spree. Parise remained a relatively consistent scorer and Suter was a credible presence on the blue line, but both were bought out nine years and nine days later, on July 13, 2021.


    Montreal Canadiens: Karl Alzner (2017)

    The 6'3", 219-pounder from British Columbia was one of the NHL's most durable defensemen during a prolonged stint with the Washington Capitals, but that fizzled in Montreal. He played one full season of 82 games with the Canadiens after getting five years and $23.125 million, but was bought out by 2020. 


    Nashville Predators: Nick Bonino (2017)

    One day, Bonino was helping the Pittsburgh Penguins to a Stanley Cup win over the Predators. A few days later, he was signed by Nashville for four years and $16.4 million with the hope he'd bring some of the title mojo with him. Instead, he scored three goals in 20 playoff games over three seasons before a trade.

Nos. 18-22: Devils, Islanders, Rangers, Senators, Flyers

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    New Jersey Devils: Ilya Kovalchuk (2010)

    The Devils got in on Kovalchuk thanks to a trade with the Atlanta Thrashers, but they had to compete to retain his services when he became a free agent after the 2009-10 season. They got him for 17 years and $102 million, but the NHL eventually nixed the deal and it was reworked. He lasted three seasons.


    New York Islanders: Andrew Ladd (2016)

    Count the Islanders in among teams that paid big money hoping players would replicate big numbers produced elsewhere. Ladd had scored 20-plus goals in five of six seasons before getting $38.5 million over seven years. He reached that number once in New York but skidded before a trade to Arizona in July.


    New York Rangers: Brad Richards (2011)

    If he'd been making regular NHL money, the 151 points Richards put up in three seasons with the Rangers wouldn't look bad. But given that he was on a nine-year, $60 million contract, it was underperforming on a big stage. New York bought him out just days after a run to the 2014 Stanley Cup Final.


    Ottawa Senators: Alexei Kovalev (2009)

    The Russian winger had been a prolific goal scorer with three NHL teams by the time the Senators signed him to a two-year, $10 million deal. At age 36, though, the magic was all but gone. He scored 32 goals in 132 games, was sent back to Pittsburgh in Year 2 of the pact and was back to the KHL soon after.


    Philadelphia Flyers: Ilya Bryzgalov (2011)

    The Flyers. Goaltending. Let's just say those two things don't tend to mesh well. Bryzgalov was coming off a solid run with the Coyotes in Phoenix when he picked up a suitcase packed with $51 million over nine years. By the end of two seasons, though, the Flyers were cutting and running with a seven-year buyout.

Nos. 23-27: Penguins, Sharks, Kraken, Blues, Lightning

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    Pittsburgh Penguins: Rob Scuderi (2013)

    Scuderi was a rugged defenseman who helped the Penguins scale the NHL mountain before he left town to sign with the Los Angeles Kings. Pittsburgh got him back four years later on a four-year, $13.5 million deal, but the sequel didn't pan out. He was pedestrian for two seasons before a trade out of town in 2015.


    San Jose Sharks: Mikkel Boedker (2016)

    Then 26, Boedker showed all the signs of an emerging NHL talent when the Sharks got him to agree to a four-year, $16 million deal. Instead, he submerged. The Danish import had 25 goals in 155 games before he was dumped to Ottawa in a multiplayer deal in 2018. He scored four more NHL goals.


    Seattle Kraken: Jaden Schwartz (2021)

    Yes, he hasn't played a shift. In fact, the team hasn't played a shift. But the idea that the Kraken, even in the hit-or-miss formative stages, shelled out $25.5 million over five seasons to a 29-year-old with some injury history is at least something of a head-scratcher. He'll be 34 when the deal wraps in 2026.


    St. Louis Blues: Jay McKee (2006)

    McKee was certainly a solid, workmanlike and capable NHL defenseman with the Buffalo Sabres through his first eight seasons. But the Blues overpaid, plain and simple. The four-year, $16 million deal was even more bloated 15 years ago. And McKee was gone to Pittsburgh after the close of Year 3.


    Tampa Bay Lightning: Vincent Lecavalier (2008)

    Go to any Lightning game these days and you'll see an arena dotted with Lecavalier's No. 4 jerseys. The fact that he led a Cup-winning team in 2004 allows for hero worship. But the 11-year, $85 million deal he got a few years after the title quickly soured as his numbers dipped. A buyout came after Year 4.

Nos. 28-32: Maple Leafs, Canucks, Golden Knights, Capitals, Jets

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    Ann Heisenfelt/Associated Press

    Toronto Maple Leafs: David Clarkson (2013)

    Clarkson had worked himself into an important role with the New Jersey Devils by the end of the 2012-13 season, when the Maple Leafs decided it was time to up the ante. They made Clarkson a seven-year, $36.75 million offer, but quickly regretted it. He lasted less than two seasons before a trade to Columbus.


    Vancouver Canucks: Loui Eriksson (2016)

    Eriksson certainly picked a lucrative time to score 30 goals. He maxed out in 2015-16 with the Boston Bruins, just in time to get the Canucks to jump on a six-year, $36 million contract. He scored 38 goals across the first five years of the deal before a salary-dump trade to Arizona this summer.


    Vegas Golden Knights: Vadim Shipachyov (2017)

    OK, this one doesn't have the long-term bruising that some of the others do. The Golden Knights have only been around a few years, and Shipachyov played exactly three games in the NHL. He signed a two-year, $9 million deal, but the pact was ripped up after the player headed back to the KHL. 


    Washington Capitals: Michael Nylander (2007)

    The 34-year-old Swede had made the rounds long before returning to Washington in 2007. Nylander played with the Hartford Whalers and five other teams, not to mention the Capitals, since 1992 on the way to a four-year, $16.5 million trip back in time. He spent two years in the NHL and two in the AHL.


    Winnipeg Jets: Olli Jokinen (2012)

    Jokinen, a 33-year-old from Finland, was trending well after a 23-goal season with the Calgary Flames in 2011-12, which prompted the Jets to dangle a two-year, $9 million deal. He scored just seven goals in Year 1 before ticking up to 18 in Year 2—still well short of what the Jets were expecting.