Ranking the 10 Worst NHL Unrestricted Free-Agent Contracts Since 2000

Lyle Richardson@@SpectorsHockeyFeatured ColumnistOctober 15, 2020

Ranking the 10 Worst NHL Unrestricted Free-Agent Contracts Since 2000

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    Tony Gutierrez/Associated Press

    It's been almost a week since the 2020 NHL free-agent market opened. A handful of unrestricted free agents, such as Alex Pietrangelo, Torey Krug and Jacob Markstrom, signed expensive long-term contracts despite a flattened salary cap and economic uncertainty generated by COVID-19 hanging over next season.

    Whether those signings end up among the NHL's worst remains to be seen. A number of UFA signings, such as the Minnesota Wild inking Zach Parise and Ryan Suter or the Vancouver Canucks signing Loui Eriksson turned into expensive failures over the past 20 years. Often, those deals failed to pan out because the player was past his prime or overpaid based on one strong season.

    Here's our ranking of the 10 worst NHL free-agent contracts handed out since 2000. They should all stand as cautionary tales for every general manager, warning of the folly of succumbing to auction fever during the opening days of free agency. The rankings are determined by contract, performance and effect upon a team's salary-cap payroll.

    The following rankings do not account for players such as former Philadelphia Flyers goaltender Ilya Bryzgalov who were acquired via trade and subsequently signed with their new team before the UFA market opened.

10. Columbus Blue Jackets Sign Nathan Horton

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    Jay LaPrete/Associated Press

    The Columbus Blue Jackets were seeking a scoring forward in the 2013 free-agent market to replace former captain Rick Nash, who was traded to the New York Rangers the previous summer. They thought they found him in Nathan Horton, signing him to a seven-year, $37.1 million contract on July 5, 2013.

    A skilled, physical right wing, Horton tallied 20 or more points in eight straight seasons from 2005-06 to 2012-13 and 50-plus points four times with the Florida Panthers and Boston Bruins. He was part of the Bruins' Stanley Cup championship in 2011 with 17 points in 21 postseason games and their run to the 2013 Cup Final with 19 points in 22 playoff contests.

    Horton, however, was also hampered by injuries during his final two seasons with the Bruins. A concussion sidelined him for the final four games of the 2011 Cup Final. A second concussion waylaid him for the final 36 games of the 2011-12 regular season and all seven of the Bruins' playoff games that spring.

    His injury history, however, didn't deter the Blue Jackets from signing him.

    Soon after the deal, Horton underwent offseason shoulder surgery that forced him to miss the first half of the 2013-14 season. He managed just 36 games before suffering a season-ending abdominal injury. That fall, he was diagnosed with degeneration of the lumbar region of his spine that ended his playing career.

    On Feb. 26, 2015, the Jackets traded Horton's contract to the Toronto Maple Leafs for David Clarkson. The Leafs would keep him on long-term injury reserve as a means of garnering some salary-cap wiggle room to invest in other players.

    Horton cannot be blamed for the way his playing career ended. Nevertheless, his injury history should've been a red flag to Jackets management.

9. Toronto Maple Leafs Sign David Clarkson

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    Julio Cortez/Associated Press

    After spending seven seasons with the New Jersey Devils, David Clarkson hit the free-agent market for the first time in 2013. The Toronto Maple Leafs snapped him up with a seven-year, $36.75 million contract.

    A physical right wing who tallied 30 goals in 2011-12, Clarkson followed up with 15 goals and 24 points in 48 games during the lockout-shortened '12-13 campaign. The Toronto Sun (h/t Joe Yerdon of NBC Sports) heralded Clarkson's arrival with a front-page spread on July 6, comparing him to fabled Leafs captain Wendel Clark.

    Clarkson, however, was no power forward like Clark.

    He managed just five goals and 11 points in 60 games during his first season with the Leafs in 2013-14, including an automatic 10-game suspension for leaving the bench during a preseason game against the Buffalo Sabres to take part in a fight. The following season was no better as he netted 10 goals and 15 points in 58 games.

    Traded to the Columbus Blue Jackets in 2014-15, Clarkson saw action in just 26 games with his new team as injuries began to take a toll. He was placed on long-term injury reserve after failing his training-camp physical in 2016.

    Clarkson's playing career was over, but his contract would be passed around. The Jackets traded it to the Vegas Golden Knights in 2017. Two years later, they traded it back to the Leafs, who used it to exceed the salary cap for 2019-20. 

8. New York Rangers Sign Wade Redden

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    Keith Srakocic/Associated Press

    The New York Rangers were in the market for a skilled top-pairing defenseman when the 2008 NHL free-agent market opened. They thought they found him in Wade Redden, signing him to a six-year, $39 million contract.

    Redden had completed 11 seasons with the Ottawa Senators and was considered among the league's best puck-moving blueliners. He was a key part of the Senators' defense corps for most of his tenure in Ottawa, including their run to the 2007 Stanley Cup Final.

    While his production dropped to 38 points over 80 games in 2007-08, it didn't deter the Rangers from signing him. While the annual average value of Redden's new contract was $6.5 million, he earned $8 million in actual salary in each of the first two seasons.

    The Rangers would soon regret that deal as Redden's best seasons were behind him. He managed just 26 points over 81 games in his first season with the Blueshirts. His production dropped in 2009-10 to just 14 points in 75 games.

    Redden was waived and demoted to the minors for the next two seasons. He received a compliance buyout following the lockout-shortened 2012-13 season and signed a one-year, $1 million deal with the St. Louis Blues. He was traded to the Boston Bruins later that season. On Jan. 9, 2014, he announced his retirement.

7 and 6: New York Rangers Sign Chris Drury and Scott Gomez

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    Frank Franklin II/Associated Press

    The implementation of the NHL salary-cap system in 2005 didn't prevent the New York Rangers from making expensive forays into the unrestricted free-agent market two years later. Seeking depth at center on July 1, 2007, they signed Scott Gomez to a seven-year, $51.5 million contract and Chris Drury to a five-year, $35.25 million deal.

    Gomez was a two-time Stanley Cup champion and winner of the 1999-00 Calder Memorial Trophy with the New Jersey Devils. He was one year removed from a career-high 84-point performance in 2005-06. Though his production the following season dropped to 60 points, that didn't prevent the Rangers from giving him an annual average value of $7.36 million.

    Drury, meanwhile, was also a former Calder Trophy winner (1998-99) who won a Stanley Cup with the Colorado Avalanche. A skilled two-way forward who co-captained the Buffalo Sabres, he was coming off a career-high 37-goal, 69-point effort in 2006-07. Signing him cost the Rangers an annual salary-cap hit of $7.05 million.

    It didn't take long for those two contracts to become burdensome for the Rangers.

    After two years, they shipped Gomez to the Montreal Canadiens in a six-player deal. He lasted three seasons with the Canadiens before they used a compliance buyout in 2013. He went on to play four more seasons with five teams, including a brief return to the Devils in 2014-15, before retiring in 2016.

    Drury tallied 58 and 56 points, respectively, in his first two seasons with the Rangers, but his performance declined as injuries began to catch up with him. He managed 32 points over 77 games in 2009-10 and five points in 24 games the following season. The Rangers bought out the final season of his contract in 2011, and he retired soon afterward.

5. New York Rangers Sign Brad Richards

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    Chris Szagola/Associated Press

    Brad Richards entered the 2011 free-agent market with an impressive 10-year NHL resume. It's what motivated the New York Rangers to outbid the Calgary Flames, Los Angeles Kings and Toronto Maple Leafs to sign the center to a nine-year, $60 million contract. The annual average value was $6.67 million, but the deal was heavily front-loaded, paying $57 million in actual salary over the first six years.

    The Rangers' pursuit of Richards was understandable. He won a Stanley Cup with the Tampa Bay Lightning in 2003-04, along with the Conn Smythe Trophy and Lady Byng Trophy. The only time he tallied fewer than 62 points was when he netted 48 in 56 games during an injury-shortened 2008-09 with the Dallas Stars. He was coming off a 77-point performance in 72 games with the Stars in 2010-11.

    Richards tallied a respectable 66 points in 82 games during his first season (2011-12) with the Rangers, as well as 15 points in 20 playoff games. However, those weren't the types of numbers worthy of the $12 million in actual salary he made that season. He followed up with 34 points in 46 games during the lockout-shortened 2012-13 season and 51 points over 82 games in 2013-14.

    With Richards dropping down the roster depth chart as his play declined, it was clear his contract was an expensive mistake. The Rangers used a compliance buyout to shed his cap hit from their books. While it won't count against their salary-cap payroll, they will be paying him two-thirds the remaining value of his contract until 2025-26.

    That buyout wasn't the end of Richards' NHL career. He signed a one-year, $2-million contract with the Chicago Blackhawks in 2014-15, helping them win a Stanley Cup as a checking-line forward. He joined the Detroit Red Wings for 2015-16 and retired on July 20, 2016.

4. New York Islanders Sign Andrew Ladd

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    Paul Sancya/Associated Press

    The New York Islanders were coming off their first playoff series victory since 1993 when they headed into the 2016 free-agent market seeking an experienced winger with leadership skills. Then-general manager Garth Snow signed Andrew Ladd to a seven-year, $38.5 million contract.

    Ladd seemed the perfect fit. A Stanley Cup champion with the Carolina Hurricanes in 2006 and Chicago Blackhawks in 2010, he captained the Atlanta Thrashers/Winnipeg Jets from 2010-11 to 2015-16. A physical two-way left winger, he had five seasons with 23-plus goals and four with 50 or more points. He also tallied 46 points in 48 games during the lockout-shortened 2012-13 campaign.

    Only a year removed from a career-best 62-point season in 2014-15, Ladd seemed to be a solid addition to the Islanders. However, his production dropped sharply with his new club. While he managed 23 goals in 2016-17, he also had just eight assists. His numbers fell to only 29 points the following season.

    Ladd appeared in just 26 games in 2018-19 before a torn ACL ended his season. He spent all but four regular-season games last season in the minors and saw action in just one playoff game during the Isles' run to the 2020 Eastern Conference Final.

    With the Islanders carrying $72.6 million invested in 20 players with Mathew Barzal and Ryan Pulock to re-sign, Ladd's $5.5 million annual cap hit has become a headache for current general manager Lou Lamoriello. The winger has a 15-team no-trade list, and the decline in his play means Lamoriello will have a difficult time finding suitors to take that contract off his hands. 

3. Vancouver Canucks Sign Loui Eriksson

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    Brynn Anderson/Associated Press

    After missing the playoffs in 2016, the Vancouver Canucks sought a winger to skate alongside the Sedin twins. They thought they found the right fit by signing right winger Loui Eriksson to a six-year, $36 million contract.

    Eriksson had played well with the Sedins on Sweden's national team, so it was assumed he'd mesh with them on the Canucks. A three-time 70-point winger with the Dallas Stars earlier in his NHL career, Eriksson was coming off a 30-goal, 63-point performance with the Boston Bruins in 2015-16.

    Things didn't work out as hoped for Eriksson or the Canucks. He managed 24 points in 2016-17, 23 the following season and 29 in 2018-19 as age and injuries began to affect his play.

    During that period, the Sedins retired while the Canucks transitioned toward younger, faster talent such as Elias Pettersson, Brock Boeser and Quinn Hughes. Eriksson tumbled down the depth chart, managing just 13 points in 49 games last season.

    Eriksson's $6 million annual average value has become a millstone for the Canucks, sparking trade and contract-buyout rumors. His contract may have cost them the opportunity to re-sign Jacob Markstrom and Tyler Toffoli.

2 and 1: Minnesota Wild Sign Zach Parise and Ryan Suter

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    Jim Mone/Associated Press

    The Minnesota Wild stunned the hockey world in July 2012 by signing left wing Zach Parise and defenseman Ryan Suter. Considered the two top players in that summer's UFA market, the duo inked identical 13-year, $98 million contracts.

    While the average annual values of both contracts were $7.5 million, they were heavily front-loaded. Parise and Suter were each set to earn $12 million in actual salary during the first two seasons, $11 million during the third, $9 million for the following five years, $8 million in 2020-21, $6 million in '21-22, $2 million in '22-23 and $1 million for the final two years. They also received full no-movement clauses.

    The Wild considered Parise and Suter the foundational pieces who would turn them into a Stanley Cup contender. However, they haven't made much progress in the years since those two signed those hefty contracts. In the last eight years, they have only advanced to the second round twice.

    Parise and Suter aren't to blame for that failure to improve. They've often been the Wild's best players and leaders during their tenure. However, the management through most of that period failed to adequately build up the roster around them.

    With Parise now 36 and Suter 35, they're no longer in their playing primes. Injuries have also frequently sidelined Parise. However, they still have five more seasons remaining on their contracts with their combined $16 million cap hit making a big dent in the Wild's payroll.

    The club is continuing to pay big money to two depreciating assets.

    Player contract details via NHL.com and Cap Friendly.