Worst Hockey Contracts of All Time

Bad hockey deals aren't a new thing. Teams have been overpaying underperforming players for years.

Worst Hockey Contracts of All Time

Sean Avery played only 23 games with the Dallas Stars after signing a four-year, $15.5 million deal in 2008.

Bad contracts in hockey aren't a new thing.

Going back a half-century, teams have ended up overpaying players who underperform on the ice for years.

But who has the ugliest deal of them all?

These are the worst contracts in hockey history.

25. Alexei Yashin

Year signed: 2001

Team: New York Islanders

Contract: 10 years, $87.5 million

Return on investment: Yashin averaged 0.84 points per game with the Islanders, good for 13th in the NHL among all centers from 2001 to 2007.

Bottom line: Referred to (unflatteringly) as Alexei Cash-in, Yashin was productive for the Islanders despite constant questions about his dedication.

The Russian centerman registered 290 points in 346 games on Long Island, before he was bought out in June 2007.

24. Sheldon Souray

Year signed: 2007

Team: Edmonton Oilers

Contract: 5 years, $27 million

ROI: Souray scored more goals in one season in Edmonton (23 goals in 2008-09) than he did in his other two years combined (7 goals between 2007-08 and 2009-10).

Bottom line: "Get the hell out," Hall of Fame head coach Pat Quinn told reporters about Sheldon Souray, after the hard-shooting blueliner asked to be dealt from Edmonton.

The Oilers received one impact season from Souray — he racked up 23 goals in 2008-09. Otherwise, Souray's tenure in Edmonton was pockmarked by serious injuries and a public spat with team management over how these injuries were handled.

Edmonton bought out Souray in June 2011.

23. John LeClair

Year signed: 2001

Team: Philadelphia Flyers

Contract: 5 years, $45 million

ROI: LeClair scored just four goals in 36 playoff games during this five-year deal.

Bottom line: On one hand, the titanic John LeClair was one of the dominant power forwards of his generation, ringing up 235 goals in a five-year span from 1995 to 2000.

On the other hand, in the summer of 2001, the free-agent winger was coming off a serious back injury and was 31 years old.

You can guess how this one went. Over the life of this contract, LeClair scored just 90 goals, ending his NHL career with cross-state rival Pittsburgh.

22. Mark Messier

Year signed: 1997

Team: Vancouver Canucks

Contract: 5 years, $30 million

ROI: After signing Messier, the Canucks went from a 77-point team to a 64-point team.

Bottom line: If a bad contract is measured by how much a player is reviled after leaving town, Messier would "win" this contest in a landslide.

Whether it's right to blame Messier or not, he's deemed the man who destroyed the late 1990s Canucks.

His ballyhooed arrival in Vancouver is still regarded as the catalyst for the eventual trade of fan-favorite Trevor Linden. Kirk McLean, Martin Gelinas, and Pavel Bure soon followed.

And while Messier was productive, his 162 points over three Canuck campaigns were a far cry from expectations. Vancouver also didn't make the playoffs once with the Hall of Fame center.

The Canucks cut short the Messier era, declining to pick up the team option on him after the 1999-00 season.

21. Milan Lucic

Year signed: 2016

Team: Edmonton Oilers

Contract: 7 years, $42 million

ROI: Lucic scored 23 goals in his first season in Edmonton, but followed with just 16 over his next two years.

Bottom line: Milan Lucic was supposed to ride shotgun for Connor McDavid on the ascending Oilers.

Instead, after one solid season in Edmonton, Lucic crashed and burned, scoring just 16 goals in the 2017-18 and the 2018-19 seasons combined. Not coincidentally, the Oilers missed the playoffs in both campaigns.

In a swap of bad contracts, Edmonton sent Lucic to Calgary for James Neal in the summer of 2019. We'll see if the veteran forwards can redeem themselves on opposite sides of the Battle for Alberta.

20. Cody Hodgson

Year signed: 2013

Team: Buffalo Sabres

Contract: 6 years, $25.5 million

ROI: Hodgson played just 189 games over the life of this contract.

Bottom line: It made sense on paper.

The 22-year-old Cody Hodgson was coming off a career season and appeared on the cusp of NHL stardom, so the Sabres locked him down for six years.

But a rare muscle disease prevented Hodgson from fulfilling his potential, and his contract was bought out in 2015. He retired the next season.

19. Mikhail Grabovski

Year signed: 2014

Team: New York Islanders

Contract: 4 years, $20 million

ROI: During the expansion draft, the Islanders had to include a first-round pick to get the Golden Knights to take the last year of Grabovski's contract.

Bottom line: Over his career, Mikhail Grabovski was the recipient of not just one, but two ill-advised contracts.

One year after inking Grabovski to a five-year, $27.5 million dollar pact, the Maple Leafs bought Grabovski out in July 2013.

The next summer, the Islanders bet on the Belarusian forward. In return, New York received 18 goals over two injury-plagued campaigns.

Because of concussions, Grabovski was unable to finish out this contract.

18. Brad Richards

Year signed: 2011

Team: New York Rangers

Contract: 9 years, $60 million

ROI: Richards scored just 28 points in 55 playoff games with the Rangers.

Bottom line: Three seasons into his nine-year agreement with the Rangers, Brad Richards was toiling on the fourth line.

When the former Conn Smythe winner was signed with New York in July 2011, the 31-year-old was hoping to rekindle the same magic with head coach John Tortorella that brought them the Stanley Cup in Tampa Bay in 2004.

But while New York did reach the Eastern Conference finals in 2012 and the Stanley Cup Final in 2014, Richards's game continued to deteriorate. Following their loss in the Stanley Cup Final, the Rangers bought him out.

The next year, Richards won another Stanley Cup, this time with the Chicago Blackhawks. Meanwhile, New York will be paying out Richards until 2026.

17. Vincent Lecavalier

Year signed: 2008

Team: Tampa Bay Lightning

Contract: 11 years, $85 million

ROI: In the four years leading up to this extension, Lecavalier averaged 39.8 goals per season. In the four years after this extension, he averaged 25 goals per game.

Bottom line: "This guy is the franchise," then-Tampa Bay Lightning coach Barry Melrose said of Vincent Lecavalier. "He is going to be a Tampa Bay Lightning probably until he retires."

Things were looking up in the Sunshine State when Tampa Bay inked the 28-year-old Lecavalier to an 11-year extension in July 2008.

Lecavalier was coming off a 40-goal campaign. New owners Oren Koules and Len Barrie had bravado. Veteran coach Melrose was going behind the bench for the first time in 13 years.

What could go wrong, except everything?

Melrose was fired 16 games into the new season. In February 2010, Koules and Barrie sold the Lightning. And in June 2013, with six years left in what was supposed to be a retirement contract, Tampa Bay bought out the rest of Lecavalier's deal.

Lecavalier didn't perform poorly from 2008 to 2013, scoring more than 20 goals four times, but he had become a merely good player making franchise star money.

16. Tuomo Ruutu

Year signed: 2012

Team: Carolina Hurricanes

Contract: 4 years, $19 million

ROI: Ruutu scored 19 goals over the life of this contract.

Bottom line: Tuomo Ruutu scored just nine goals two years into his generous four-year extension before Carolina shipped him off to New Jersey.

In fairness, Ruutu's in-your-face style made him injury-prone. Ruutu didn't fare much better with the Devils, adding just 10 goals to close out his NHL career.

In 2015-16, his final NHL campaign, Ruutu went 32 games without scoring a point, before he notched an assist in the second period of the last game of the year.

15. Stephen Weiss

Year signed: 2013

Team: Detroit Red Wings

Contract: 5 years, $24.5 million

ROI: Weiss scored just 29 points in two seasons in Detroit.

Bottom line: Stephen Weiss was a rock-steady performer in Florida, notching over 40 points in six straight seasons. Meanwhile, Detroit was looking for a pivot to anchor their second line for the years to come, so they turned to the 30-year-old Weiss in the summer of 2013.

But Weiss's production sunk like a rock, in part because of injuries. The centerman didn't even manage to score 40 points over his entire Red Wings career, totaling just 29 points in two years.

Weiss was bought out in June 2015. Detroit is paying him off until 2021.

14. Matt Moulson

Year signed: 2014

Team: Buffalo Sabres

Contract: 5 years, $25 million

ROI: The Sabres paid $714,285.71 for each goal that Moulson scored for them.

Bottom line: Buffalo thought they were getting a reliable 20-goal scorer when they landed the 30-year-old Matt Moulson in the summer of 2014. They got a lot less than that.

Moulson scored 35 goals in 253 games for the Sabres. To compare, in 2011-12, he scored a career-high 36 goals for the Islanders.

Moulson finished out the last two years of his contract in the AHL.

13. Ilya Bryzgalov

Year signed: 2011

Team: Philadelphia Flyers

Contract: 9 years, $51 million

ROI: Bryzgalov's save percentage in Arizona was .917. It dropped to .905 in Philadelphia.

Bottom line: The 31-year-old Ilya Bryzgalov was considered one of the best goalies in the NHL when Philadelphia lured him away from Arizona with a nine-year contract in June 2011.

Just two middling campaigns later, the Flyers bought out Bryzgalov.

Bryzgalov played just 40 more NHL games before calling it quits after the 2014-15 season.

Philadelphia will be paying the eccentric Russian netminder off until 2027.

12. Martin Lapointe

Year signed: 2002

Team: Boston Bruins

Contract: 4 years, $20 million

ROI: Lapointe scored just two goals and four points in 18 playoff games with the Bruins.

Bottom line: When Martin Lapointe's agent told Ken Holland what Boston was giving Lapointe, the Detroit general manager allegedly replied: "You're lying."

The Bruins, however, weren't kidding around when they gave a grinder coming off a career-best 27-goal season $20 million dollars.

It took Lapointe three years in Boston to score 27 goals. He ended up with 40 as a Bruin before moving on to Chicago after the canceled 2004-05 season.

11. Nathan Horton

Year signed: 2013

Team: Columbus Blue Jackets

Contract: 7 years, $37.1 million

ROI: Horton played 36 games with the Blue Jackets and hasn't played in six of the last seven seasons of his contract.

Bottom line: Columbus thought they were reeling in a goalscorer in his prime when they inked the 28-year-old Nathan Horton to a seven-year pact in July 2013.

Unfortunately, Horton's back didn't cooperate, and he played just one season with the Blue Jackets, scoring five goals.

He hasn't played since. Horton is in the last year of his contract, currently being paid out by Toronto, which swapped out David Clarkson's equally pernicious contract for his in 2015.

10. Wade Redden

Year signed: 2008

Team: New York Rangers

Contract: 6 years, $39 million

ROI: Over the life of this contract, Redden played in 185 NHL games — and 119 AHL games.

Bottom line: When the Rangers sent Wade Redden to the minors in September 2010, the defenseman became the highest-paid player ever to suit up in the AHL.

This was just two seasons after New York signed Redden to a massive six-year contract.

Redden toiled for two seasons in the AHL, before the Rangers bought him out in January 2013.

The move paved the way for the defender's brief return to the NHL in 2012-13, his last season in the league.

9. Dave Bolland

Year signed: 2014

Team: Florida Panthers

Contract: 5 years, $27.5 million

ROI: Bolland spent the last three years of this contract on the Coyotes roster, but he never played a game for Arizona.

Bottom line: Dave Bolland, a well-rounded, two-time Stanley Cup winner, was a big addition for the perennial loser Panthers in the summer of 2014.

However, injuries conspired to cut short Bolland's Florida career, as he notched just 28 points over parts of two seasons before retiring in 2016.

8. David Clarkson

Year signed: 2013

Team: Toronto Maple Leafs

Contract: 7 years, $36.75 million

ROI: Clarkson scored just 15 goals in 118 games with the Leafs.

Bottom line: This is considered the worst contract in Maple Leafs history, which is saying something.

It's not to say that Clarkson wasn't a solid player. When the hard-nosed winger hit the open market in the summer of 2013, the speculation was that as many as 20 organizations showed interest.

But committing seven years to a merely solid 29-year-old was a mistake from the beginning. This, compounded by injuries, resulted in Clarkson scoring just 15 goals in two seasons with the Leafs.

Toronto traded Clarkson to Columbus in 2015 for Nathan Horton. It was an exchange of bad contracts — the injured Horton never suited up for the Maple Leafs. Clarkson played just 26 games for the Blue Jackets, before they passed on his poison pill contract to the expansion Golden Knights.

The injured Clarkson never played for Vegas.

But what goes around comes around. In 2019, Vegas sent Clarkson's contract back to Toronto. In a convoluted, but clever bit of salary cap manipulation, Clarkson and Horton's contracts (Horton is still on the books, too) will give the Maple Leafs more cap space in 2019-20.

Meanwhile, for Clarkson, it doesn't matter who's cutting his checks — he's still getting them. He's now the coach of his local high school hockey team.

7. Chris Gratton

Year signed: 1997

Team: Philadelphia Flyers

Contract: 5 years, $16.5 million

ROI: Gratton scored just 23 regular-season goals in a Flyers uniform.

Bottom line: Four first-round draft picks. That's what Philadelphia ended up giving Tampa Bay after the Flyers signed Chris Gratton to a controversial five-year, $16.5 million dollar pact.

The 22-year-old pivot was the third overall pick of the 1993 draft, but he also had scored an unremarkable 67 goals in his first four years in the NHL.

The Lightning returned the picks to Philly, in exchange for Mikael Renberg and Karl Dykhuis. Meanwhile, Gratton, mainly because of an eye-popping $9 million signing bonus, became the second-highest-paid player in the league during the 1997-98 season.

However, after notching just one goal in 26 games in 1998-99, Philadelphia gave up on Gratton, returning him to Tampa Bay, for, you guessed it, Renberg.

Gratton lasted in the NHL for another decade, carving out a career as a solid two-way center.

6. Sean Avery

Year signed: 2008

Team: Dallas Stars

Contract: 4 years, $15.5 million

ROI: Avery played just 23 games in Dallas before they cut him.

Bottom line: Even Sean Avery's head coach and teammates in Dallas didn't want him in the locker room.

Just 23 games into his first season with the Stars, Avery was suspended after making crude, public comments about another player's girlfriend. He was not welcomed back with open arms by his teammates.

"Their voice was heard loud and clear," Dallas general manager Brett Hull admitted.

The Stars were at least able to avoid buying out Avery. They cut the pesky winger in March 2009, but the Rangers claimed him.

5. Ville Leino

Year signed: 2011

Team: Buffalo Sabres

Contract: 6 years, $27 million

ROI: Buffalo 10 goals for $27 million, which translates to $2.7 million per goal.

Bottom line: Ville Leino called his last year in Buffalo, "Jail."

In 2013, Leino painted "Jail," which he turned into a hoodie for his fashion company Billebeino in 2017.

Leino described his last season in Buffalo on Instagram: "I was playing my third year in Buffalo Sabres with long and big contract. Things weren't working with me and the team. I was getting a lot of pressure and heat and there was no way out of it. I felt trapped and down. All I could do was get up every morning and go to work and try to make it work. This painting reflects those feelings that I was going through on that period of time."

Of course, the Sabres probably felt just as trapped as Leino by the six-year deal that they handed out to the then 27-year-old in July 2011. The Finnish forward scored just 10 goals in 137 games in Buffalo, before the Sabres bought him out in June 2014.

Leino never played another game in the NHL.

4. Bobby Holik

Year signed: 2002

Team: New York Rangers

Contract: 5 years, $45 million

ROI: Holik's 2003-04 Rangers finished 22 points out of the playoffs.

Bottom line: Perhaps no contract was more emblematic of the Wild West that was NHL spending in the pre-salary cap era than the five-year, $45 million dollar deal that the Rangers gave Bobby Holik in July 2002.

While there's no doubt that Holik was an integral part of two Stanley Cup-winning New Jersey squads, the 31-year-old was, well, 31. He also was more of a second-line center than a frontline pivot.

Holik was a solid performer under the Madison Square Garden lights, but was far from a difference-maker. New York failed to make the playoffs in his first two years on Broadway, and the Rangers bought out his contract in July 2005.

3. Rick DiPietro

Year signed: 2006

Team: New York Islanders

Contract: 15 years, $67.5 million

ROI: Over the life of his 15-year contract, DiPietro won 72 games for New York. That's near a million per win— $937,500 per victory, to be exact.

Bottom line: When the Islanders signed 24-year-old goaltender Rick DiPietro to a 15-year contract in September 2006, it was the longest NHL contract ever handed out.

It's a still-standing record, tied in 2012 by the New Jersey Devils and Ilya Kovalchuk.

Beset by injuries, DiPietro managed just two healthy seasons. In a particularly painful five-year stretch, between 2008 to 2013, the netminder played just 50 games.

DiPietro was bought out after 2012-13, with eight seasons left on his mammoth contract. He retired the next year.

New York will be paying DiPietro through 2029.

2. Jeff Finger

Jeff Fingers — Jeff Finger scored eight goals in 105 games with the Maple Leafs.

Year signed: 2008

Team: Toronto Maple Leafs

Contract: 4 years, $14 million

ROI: Finger was given his outright release halfway into the contract.

Bottom line: This signing was so inexplicable hockey analytics guru Daniel Tolensky made a strong case that Maple Leafs management had literally confused Finger with another defenseman.

Finger played just 94 games for Colorado when Toronto rewarded him with a lucrative four-year offer. He skated in just 105 more games for the Leafs before the organization waived him in October 2010.

"It’s not so much just a business move," Toronto head coach Ron Wilson admitted. "We’ve got seven guys better than him right now."

Finger never appeared in the NHL again.

1. Derek Sanderson

Year signed: 1972

Team: Philadelphia Blazers (WHA)

Contract: Five years, $2.65 million

ROI: Sanderson scored just three goals for the Blazers before Philadelphia bought him out.

Bottom line: The World Hockey Association's Blazers made Derek Sanderson the highest-paid professional athlete in the world in 1972. The beneficiary of an upstart league that wanted to compete with the NHL, Sanderson, a good-but-not-great forward, made more money that year than Bobby Hull, Wilt Chamberlain, Joe Namath, or Pele.

Speaking of Hull, the 33-year-old was lured to the WHA about a month before Sanderson with a similarly unheard-of million dollar offer. But when the Winnipeg Jets signed the winger, the 10-time NHL All-Star was still considered one of the sport's premier talents.

Not so with Sanderson. While Sanderson was just 26, he was nowhere as accomplished as Hull. What Sanderson oozed was charisma — enough that Philadelphia was willing to bet on his box-office appeal.

But injuries and increasing substance abuse hampered Sanderson's chances of living up to his record-setting pact. After just eight games with the Blazers, Sanderson was bought out by ownership for a million dollars.

The fast-living Sanderson continued in the NHL for five more seasons on five different teams, before hanging up the skates for good.