Free agency is rarely a good place to spend money as an NHL general manager.
Teams typically have to overpay to lure talented free agents away from their previous teams, and with a hard salary cap, these moves — particularly the ones with longer term — tend to age worse.
These are the worst free agent contracts of the salary-cap era (2005-06).
1. Jeff Skinner
Position: Left wing
Year: 2019
The contract/team: 8 years, $72 million with the Buffalo Sabres
The skinny: How can a contract be so bad so soon? Consider that the COVID-19 pandemic has forced a flat salary cap for the foreseeable future in the NHL, and Skinner is clogging up almost 10 percent of Buffalo’s cap for the next six seasons.
That’d be a problem if Skinner were producing at an elite level, instead he has scored just 21 goals in 112 games and already been a healthy scratch over his two seasons since he signed the deal.
Did we also mention there’s six more seasons left?
2. Ilya Bryzgalov
Position: Goalie
Year: 2011
The contract/team: 9 years, $51 million with the Philadelphia Flyers
The skinny: The Flyers signed Bryz to be their franchise goalie, and he was one of the great characters in hockey, and this contract fortunately gave us all insights into his belief system via Philadelphia’s appearance on HBO’s “Road to the Winter Classic” series in 2011-12.
Bryzgalov played just 99 games in a Flyers uniform, posting ghastly numbers (.905 save percentage, 2.60 goals-against average) before they bought out the contract after just two seasons.
Making matters worse, the Flyers offloaded future star Sergei Bobrovsky in 2012 to make room for Bryzgalov in net.
3. David Clarkson
Position: Right wing
Year: 2013
The contract/team: 7 years, $36.7 million with the Toronto Maple Leafs
The skinny: Clarkson was a 30-goal scorer in New Jersey when the Maple Leafs made him one of the highest-paid players of the 2013 offseason.
The contract was panned at the time and made worse by the fact Clarkson scored just five goals in 60 games in the first year.
He spent only a season-and-a-half in Toronto before he was traded to Columbus. The Blue Jackets employed him for just 26 games before injuries derailed his career.
4. Milan Lucic
Position: Left wing
Year: 2016
The contract/team: 7 years, $42 million with the Edmonton Oilers
The skinny: Lucic was a stalwart for the Boston Bruins, helping them to the Stanley Cup Final twice and a Cup win in 2011.
After a year in Los Angeles, Lucic was rewarded with the long-term deal in Edmonton that was widely panned from the moment it was signed.
But his heavy style of play aged poorly, and Edmonton traded him to rival Calgary in 2019, where he’ll undoubtedly play out the remainder of his contract.
5. Ville Leino
Position: Left wing
Year: 2011
The contract/team: 6 years, $27 million with the Buffalo Sabres
The skinny: Leino parlayed a career year in Philadelphia where he scored 19 goals and had 53 points into the long-term contract in Buffalo.
But Buffalo tried to make Leino a center, and that backfired as Leino had just 10 goals and 46 points in 134 games for the Sabres before his contract was bought out after just three seasons.
6. Dave Bolland
Position: Center
Year: 2014
The contract/team: 5 years, $27.5 million with the Florida Panthers
The skinny: Bolland was a hero for two Stanley Cup championship teams in Chicago and cashed in by signing the huge contract with the Panthers as a 28-year-old.
However, he played just 78 games and posted only 28 points in a Florida uniform before injuries forced him out of the league.
Bolland received his entire contract despite the fact he could not play beyond the 2015-16 NHL season.
7. Matt Moulson
Position: Left wing
Year: 2014
The contract/team: 5 years, $25 million with the Buffalo Sabres
The skinny: Moulson earned the contract by playing with John Tavares, but when he was no longer playing next to Tavares his production cratered.
Moulson scored 30-plus goals in three consecutive seasons with the New York Islanders, however in Buffalo he scored just 35 goals in 239 games.
He was exiled to the AHL — placed on loan with the Kings minor-league affiliate — for the final two seasons of the contract.
8. Wade Redden
Position: Defenseman
The year: 2008
The contract/team: 6 years, $39 million with the New York Rangers
The skinny: Redden was a perfectly serviceable defenseman, however he was 31 when he signed a six-year contract in a league that was getting faster each year.
Redden’s foot speed diminished quickly, and he played only 156 games in a Rangers sweater before they banished him to the AHL in a cap-savings maneuver. His contract was bought out by New York in 2013.
9. Jeff Finger
Position: Defenseman
Year: 2008
The contract/team: 4 years, $14 million with the Toronto Maple Leafs
The skinny: Finger was 28 and had played just 94 NHL games when he signed his multi-year contract with the Maple Leafs on July 1, 2008.
Then-Toronto GM Cliff Fletcher had to justify the deal from the start, but it quickly became indefensible as Finger scored just 33 points in 105 games before his contract was buried in the AHL.
10. Vincent Lecavalier
Position: Left wing
Year: 2009
The contract/team: 11 years, $85 million with the Tampa Bay Lightning
The skinny: Lecavalier was a star who had delivered the Stanley Cup to Tampa when he signed the lengthy, back-diving contract – that only would’ve expired after the 2020 season.
However he was 29 when the deal kicked in, and his skillset diminished shortly thereafter.
The Lightning bought out Lecavalier’s deal after just four seasons when the NHL gave teams compliance buyouts after the 2013 lockout.
