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Frank's worst free agent signing of all time from each of the 32 NHL teams. Frank names the biggest NHL free agent busts in league history.
With the 2026-27 NHL season fast approaching following the conclusion of free agency, it's a good time to think about some of the worst free agent signings in history.
In this column, we're going to dive into each NHL team's worst free agent signing of all-time.
So, without further ado, let's get right into it. Do note that only contracts carrying an average annual value (AAV) of at least $4 million were considered.
Anaheim Ducks
Todd Bertuzzi - Two years, $8 million ($4 million AAV)
Bertuzzi’s production was not disastrous, as he recorded 40 points in 68 games during the 2007-08 season. However, Anaheim placed him on waivers and bought out the final year of his contract after just one season, making the short-lived deal one of the poorest returns on a major free-agent investment in Ducks history.
Boston Bruins
David Backes - Five years, $30 million ($6 million AAV)
Backes remained useful early in the contract, but his role declined rapidly as he moved through his 30s. He was a healthy scratch late in the 2019 Stanley Cup Final and was later waived. Boston eventually included a first-round pick and prospect Axel Andersson in the trade that sent Backes to Anaheim for Ondrej Kase.
Buffalo Sabres
Ville Leino - Six years, $27 million ($4.5 million AAV)
Leino earned his contract after a productive run with Philadelphia but never came close to replicating it in Buffalo. He scored only 10 goals and 46 points in 137 games with the Sabres, including zero goals during his final season. Buffalo used a compliance buyout with three years and $13.5 million remaining on the deal.
Calgary Flames
James Neal - Five years, $28.75 million ($5.75 million AAV)
Neal was signed to provide dependable goal-scoring but finished his first Calgary season with only seven goals and 19 points in 63 games. He was also scratched during the playoffs before the Flames traded him to Edmonton for Milan Lucic after just one year. The Oilers retained 12.5% of Lucic’s remaining salary in the trade.
Carolina Hurricanes
Scott Darling - Four years, $16.6 million ($4.15 million AAV)
Carolina acquired Darling’s negotiating rights and immediately signed him to become their starting goaltender. Instead, he went 15-25-9 with a 3.20 goals-against average and an .887 save percentage over two seasons. He was waived, traded to Florida, and bought out with two years remaining, although health also contributed to this poor showing.
Chicago Blackhawks
Cristobal Huet - Four years, $22.5 million ($5.625 million AAV)
Huet was part of Chicago’s 2010 Stanley Cup-winning team, but he lost the starting job to Antti Niemi during the championship run. With two expensive seasons still remaining, the Blackhawks loaned him to Switzerland to remove his cap hit from the NHL roster. He never played another game for Chicago.
Colorado Avalanche
Teemu Selanne - One year, $5.8 million
Selanne arrived in Colorado as part of a high-profile package with Paul Kariya, but the experiment never worked. Nagging knee problems limited the Hall of Famer to 16 goals and 32 points in 78 games, by far his least productive season to that point in his career. He was eventually demoted to the fourth line and scratched during the playoffs.
Columbus Blue Jackets
Nathan Horton - Seven years, $37.1 million ($5.3 million AAV)
This was a catastrophic outcome rather than a reflection of Horton’s effort or ability. A degenerative back condition limited him to only 36 games for Columbus before ending his career. The Blue Jackets eventually traded his uninsured contract to Toronto for David Clarkson, who was also carrying a significant long-term commitment, one that the Leafs wanted to get rid of.
Dallas Stars
Martin Hanzal - Three years, $14.25 million ($4.75 million AAV)
Hanzal was expected to give Dallas a big, dependable two-way center, but recurring back problems prevented that from happening. He appeared in 38 games during his first season and only seven in his second. Hanzal never played during the final year of the contract, finishing with 12 points in 45 games for the Stars.
Detroit Red Wings
Stephen Weiss - Five years, $24.5 million ($4.9 million AAV)
Detroit signed Weiss to replace Valtteri Filppula as its second-line center, but injuries and declining production derailed the plan almost immediately. Weiss managed only 11 goals and 29 points in 78 games over two seasons. The Red Wings bought out the final three years of his contract in 2015.
Edmonton Oilers
Milan Lucic - Seven years, $42 million ($6 million AAV)
Lucic scored 23 goals in his first Edmonton season, but his skating and production deteriorated quickly afterward. He finished with 104 points in 243 games before being traded to Calgary for James Neal after three seasons. Edmonton also had to retain 12.5% of Lucic’s remaining salary.
Florida Panthers
Dave Bolland - Five years, $27.5 million ($5.5 million AAV)
Bolland’s contract was an immediate risk because of his injury history. He never became the top-six center Florida envisioned, recording 28 points in only 78 games over two seasons. The Panthers eventually attached former first-round prospect Lawson Crouse to Bolland’s contract to get Arizona to take him on.
Los Angeles Kings
Ilya Kovalchuk - Three years, $18.75 million ($6.25 million AAV)
Kovalchuk returned from the KHL at age 35, but he never settled into a consistent role with the Kings. He recorded 43 points in 81 games and was removed from the lineup indefinitely early in his second season. Los Angeles terminated his contract in December 2019, less than halfway through the deal.
Minnesota Wild
Thomas Vanek - Three years, $19.5 million ($6.5 million AAV)
Vanek still provided some offense, producing 39 goals and 93 points in 154 games, but he never became the difference-making scorer Minnesota expected. His defensive limitations and inconsistent play eventually pushed him down the lineup. The Wild bought out the final season of the contract after only two years.
Montreal Canadiens
Karl Alzner - Five years, $23.125 million ($4.625 million AAV)
Montreal signed Alzner to strengthen its defense, but his mobility declined almost immediately. He produced only 13 points in 95 games for the Canadiens before being waived and assigned to the AHL. Montreal bought out the remaining two years of his contract in 2020 and carried the resulting cap penalties for several more seasons.
Nashville Predators
Matt Duchene - Seven years, $56 million ($8 million AAV)
Duchene was productive at times and even set a Nashville record with 43 goals during the 2021-22 season, so this was not a complete on-ice failure. However, the Predators bought him out with three years and approximately $20 million in salary remaining. That decision created six seasons of dead-cap charges, making the original commitment extremely costly.
New Jersey Devils
Ilya Kovalchuk - 15 years, $100 million ($6.67 million AAV)
This choice is a bit controversial because Kovalchuk played well and helped New Jersey reach the 2012 Stanley Cup Final, but the unprecedented length of the contract created enormous long-term risk. After only three seasons, he voluntarily retired from the NHL and returned to Russia with 12 years and $77 million remaining.
The departure turned the signing into one of the league’s most infamous contract sagas.
Ilya Kovalchuk gave the #NJDevils a 2-0 lead in Game 6 of the Eastern Conference Final vs. the Rangers on May 25, 2012. The Devils went on to win, 3-2, on Adam Henrique’s OT goal to clinch the series & send the Devils to the Stanley Cup Final. pic.twitter.com/1MVfjqfzJk
— New Jersey Devils History (@DevilsOfYore) May 25, 2026
New York Islanders
Andrew Ladd - Seven years, $38.5 million ($5.5 million AAV)
Ladd was expected to replace some of the leadership and scoring lost when Kyle Okposo and Frans Nielsen departed, but injuries and declining production quickly reduced his role. He eventually spent time in the AHL. To move the remaining contract, the Islanders sent Ladd, two second-round picks and a conditional third-round pick to Arizona.
New York Rangers
Wade Redden - Six years, $39 million ($6.5 million AAV)
Redden’s contract became a symbol of excessive free-agent spending in a salary-cap league. After two disappointing NHL seasons, the Rangers buried him in the AHL for two years to remove his cap hit. New York then used an accelerated compliance buyout with two seasons remaining on the agreement.
Ottawa Senators
Evgenii Dadonov - Three years, $15 million ($5 million AAV)
Dadonov recorded only 20 points in 55 games before Ottawa traded him after one season. The deal became even more damaging when the organization failed to properly disclose his no-trade list to Vegas. The resulting NHL sanction was revised in 2026, moving Ottawa’s first-round pick to No. 32 and imposing a $1 million fine.
Philadelphia Flyers
Vincent Lecavalier - Five years, $22.5 million ($4.5 million AAV)
Lecavalier scored 20 goals during his first season in Philadelphia, but his role diminished rapidly afterward. He became a frequent healthy scratch and produced only 20 points in 57 games during his second year. The Flyers traded him to Los Angeles midway through the contract while retaining half of his remaining salary.
Pittsburgh Penguins
Ziggy Palffy - Three years, $13.5 million ($4.5 million AAV)
Palffy was still productive, recording 42 points in 42 games during the 2005-06 season. However, a lingering shoulder problem caused him to retire halfway through the first year of the contract. The signing was a failure by outcome rather than performance, as Pittsburgh received only half a season from its major free-agent addition.
San Jose Sharks
Mikkel Boedker - Four years, $16 million ($4 million AAV)
Boedker was signed after a 51-point season to provide speed and secondary scoring for a Stanley Cup contender. He produced only 63 points in 155 games over two seasons and never secured the major offensive role San Jose envisioned. The Sharks traded him to Ottawa halfway through the contract as part of the Mike Hoffman transaction.
Seattle Kraken
Philipp Grubauer - Six years, $35.4 million ($5.9 million AAV)
Grubauer was signed to be the expansion franchise’s long-term starting goalie, but he struggled through most of the contract and was waived and assigned to the AHL in January 2025. He rebounded during the 2025-26 season, but his overall Seattle record stood at 70-90-16 with a 3.00 goals-against average and an .894 save percentage through five seasons.
St. Louis Blues
Torey Krug - Seven years, $45.5 million ($6.5 million AAV)
Krug remained productive when healthy, but he missed time during each of his first four seasons and posted a career-worst minus-31 rating in 2023-24. He then missed the entire 2024-25 season following major ankle surgery. Blues general manager Doug Armstrong said in May 2025 that Krug was not expected to play again, although his contract runs through 2026-27.
Tampa Bay Lightning
Matt Carle - Six years, $33 million ($5.5 million AAV)
Carle initially handled a regular role, but his effectiveness steadily declined as the contract progressed. He recorded only two goals and seven assists in 64 games during his final Tampa Bay season while frequently being used as a healthy scratch. The Lightning bought out the final two years of the agreement in 2016.
Toronto Maple Leafs
David Clarkson - Seven years, $36.75 million ($5.25 million AAV)
Clarkson was supposed to bring scoring, physicality and leadership to Toronto, but he managed only 15 goals and 26 points in 118 games. Less than two seasons into the contract, the Maple Leafs traded him to Columbus for the injured Nathan Horton. The move showed how desperate Toronto was to escape a deal that had become almost immediately unworkable.
Utah Mammoth
No qualifying bad signing yet
Utah has only had two years in franchise history, so they don't have a qualifying worst free agent signing just yet. Its first major qualifying free-agent addition was Anders Lee, who signed a three-year, $16.2 million contract this past July. This was a lucrative deal which carries a bit of risk, but let's see how it unfolds.
Vancouver Canucks
Loui Eriksson - Six years, $36 million ($6 million AAV)
Eriksson recorded only 38 goals and 90 points in 252 games during five disappointing seasons in Vancouver. The Canucks eventually sent him to Arizona with Jay Beagle, Antoine Roussel, a first-round pick, a second-round pick, and a seventh-round pick in the trade for Oliver Ekman-Larsson and Conor Garland.
October 15, 2016. Loui Eriksson makes his Canucks debut and scores a goal!
It just happened to be on the wrong net.
📽️: Sportsnet | NHL pic.twitter.com/HylGp9LThw
— CanucksArmy (@CanucksArmy) February 7, 2024
Vegas Golden Knights
Vadim Shipachyov - Two years, $9 million ($4.5 million AAV)
Shipachyov arrived from the KHL as one of the Golden Knights' most notable additions but played only three NHL games, scoring one goal. He was assigned to the AHL, left the affiliate, and was suspended by the organization. Vegas terminated the contract in November 2017, allowing him to return to Russia.
Washington Capitals
Michael Nylander - Four years, $19.5 million ($4.875 million AAV)
Nylander produced 37 points in 40 games during his first season before undergoing shoulder surgery, but his role diminished after he returned. Washington could not find a trade partner because of his salary and no-movement clause. The Capitals eventually loaned him to the AHL and then Europe to clear his cap hit from the NHL roster.
Winnipeg Jets
Steve Mason - Two years, $8.2 million ($4.1 million AAV)
Mason was signed to form a tandem with Connor Hellebuyck but appeared in only 13 games, going 5-6-1 with a 3.24 goals-against average. After one season, Winnipeg sent Mason, Joel Armia and two draft picks to Montreal for minor-league defenseman Simon Bourque. Montreal immediately bought out the final year of Mason’s contract.
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