When signing a new player, the dollar amount on the contract is key. I recently wrote a piece on Vancouver’s potential cap space issues. They have a lot of average players on big-money ‘no-trade’ contracts. Often, teams will shell out big bucks to get their man. However, this does not always guarantee success. For every Connor McDavid, there is an overpaid Loui Eriksson. NHL contracts are always closely scrutinized, here are some of the worst offenders.
1. Rick DiPietro
In 2006, the New York Islanders were so confident in the ability of their starting goalie. DiPietro became the first-ever goalie to be drafted first overall in 2000. Despite only posting a .915 save percentage over six years, the Islanders handed him a massive $67.5 million contract over 15 years. Apparently, the NHL front office had actively discouraged the team from doing this. His numbers during 06-07 were painful as he went 32-19-9 with a .919 save percentage and a horrific 2.58 GAA.
Their gamble did not pay off and ‘Rickiety’s’ career would soon be derailed by injuries and inconsistency. The Islanders bought out his contract in 2013 and he has not returned to pro hockey since then. This will forever rank as one of the most baffling contracts in hockey history. Although, it did serve as a blueprint as how not to handle a negotiation. DiPietro only suited up a total of 318 times in 13 years. This cemented his status as one of the worst busts of all time.
2. Ilya Bryzgalov
Goalies seem to be a particular issue when it comes to contracts. In 2011, the Philadelphia Flyers needed a solid goalie. Signing Ilya Bryzgalov to a nine-year, $51 million contract seemed a smart piece of business. Over 4 seasons in Phoenix he had always impressed and had helped them to the playoffs the season prior. Philly traded away Jeff Carter and skipper Mike Richards to LA to make the cap space work; this would be a massive oversight.
Bryzgalov was more famous for his bizarre media interviews than his play. Horrendous in the net which including a poor 2011-12 playoff campaign. During this stretch, Bryzgalov posted a dismal 3.46 GAA and a .887 save percentage in 11 games. “I have zero confidence in myself,” he said after one loss against Winnipeg and it showed. After less than two seasons, the Flyers bought out the remaining seven years of the Russian’s contract. He would round out his NHL career with short stints in Edmonton, Minnesota and Anaheim.
3. Ville Leino
Looking back, it seems strange that Buffalo took such an expensive gamble on a player who proved so little. Detroit signed Ville Leino as an undrafted free agent in 2008. He was already in his mid-20s and played two part-time seasons with the Wings. Traded to the Flyers in 2010, he proceeded to tear up the 2010 playoffs with 21 points in 19 games (still a joint record for a rookie). This was apparently enough for the Sabres to sign him to a six-year, $27 million contract.
Three underwhelming seasons followed where he didn’t score higher than 25 points. Regularly a healthy scratch during his final season, Buffalo put Leino on waivers in 2014. He returned to Europe to play his career in his native Finland, Switzerland and Latvia before retiring in 2017. This was a classic case of an unproven player unable to live up to the pressure of a high price contract.
4. Milan Lucic
It’s easy to see why the Oilers had faith in the deal. In 2016, Milan Lucic seemed like the perfect linemate and bodyguard for Connor McDavid. Eight fine years in Boston and a Stanley Cup win appeared to justify the seven-year, $42 million contract he was given. For the first season at least, Lucic’s crash and bash style proved effective. He put up 55 points and guided the Oilers back to the playoffs. Sadly, the momentum didn’t last and his next two seasons his production declined. 2017-18 saw a career-low 20 points and Edmonton’s once-promising future had completely passed.
Desperate to part ways, Lucic waved his no-trade clause. In the summer of 2019, the Oilers traded Lucic to rivals Calgary. Ironically, his replacement James Neal would prove to be an excellent replacement. Lucic continues to struggle with the Flames and so far, only has 20 points to his name even going on a 28 game goal drought. His star appeal has faded after his unfortunate tenure in Alberta.
5. Wade Redden
For the most part, Wade Redden was a consistent star during his 11-year stint with the Ottawa Senators. However, his numbers saw a drastic decline during his final two seasons, not helped by his huge $13 million, 2-year contract. After the loss of Zdeno Chara in 2005, Redden struggled to find good form. Despite some serious warning signs, Rangers GM Glen Sather signed him to a six-year, $39 million contract in 2008.
Redden would struggle mightily in the Big Apple and faced constant criticism from the New York media. After two underwhelming seasons, the Rangers bit the bullet and put their high price blueliner on waivers in 2010. He would spend the next two years in the minors with Hartford Wolf Pack and Connecticut Whale before brief NHL returns with Boston and St Louis. Redden’s high price failure would overshadow his mostly stellar career.
6. Alexei Yashin
Drafted 2nd overall in 1992, Yashin originally looked like a great future prospect for Ottawa. Runner up for the Hart trophy in 1999 after an incredible 94 points season, his production and play stunned all in the nation’s capital. Off the ice, Yashin had an acrimonious relationship with Senators management and refused to play in 1999/00 due to a contract dispute. In 2001, the Islanders (yes, them again) swooped for him in a noteworthy trade which included Zdeno Chara and a second overall pick.
Upon his arrival, GM Mike Milbury promptly signed the Russian star to a 10-year, $87.5 million contract. This would prove to be another expensive mistake for the Isles. After a great 75 point first season in 2001-02, Yashin’s production went into decline in the seasons afterwards, not helped by the team constantly shifting players. Eventually, the Islanders lost patience with their expensive star and in 2007 they bought out the remaining years of his contract which netted him a cool $17.63 million. Yashin would spend the final five years of his career back in his native Russia, retiring in 2012.
7. David Clarkson
This is one contract that Leafs fans will never live down. David Clarkson was a good player during his time at New Jersey but never scored more than 46 points in a season. Toronto brass took the bold step of handing him a seven-year, $36 million contract. Question marks were immediately raised and Clarkson repaid their faith with 11 points in 60 games during 2013-14. After only posting 15 points in 2014-15 the Leafs traded Clarkson to Columbus Blue Jackets for Nathan Horton (who hadn’t played since 2013).
Injuries would limit Clarkson to just 23 games in Columbus over one and a half seasons. Recently his contract has become an albatross among NHL clubs. The Jackets traded his contract to Vegas in 2017 in order to let them select William Karlsson. Ironically his contract was traded back to the Leafs in 2019 for Garrett Sparks. Clarkson was a tragic case of an average player who was grossly overpaid.
Fun fact: I was in attendance at the ACC for his first-ever Leafs goal in 2013; the relief among supporters was palpable.
8. Sheldon Souray
In 2007 Souray was hot property in the free-agent market. His 64 points for Montreal the previous season made him a hot commodity. The Oilers signed Souray to a five-year, $27 million deal. Sadly, injuries limited him to just 23 games in his first season. He rebounded with 53 points in 2008-09 and gained a third All-Star appearance. However, his injury problems continued during the next season which saw him only appear in 37 games. Souray asked for a trade but unsurprisingly there were zero takers for his huge contract.
The Oilers would put him on waivers and assign him to AHL side Hershey Bears before buying out of his contract in 2011. Souray would play two further seasons with Dallas (where he was briefly a fan favourite) and Anaheim. He never regained the scoring prowess of his final year in Montreal.
9. Dave Bolland
Although he scored the cup-winning goal in 2013 for Chicago, Dave Bolland was never a big-time player. That didn’t stop the Florida Panthers from shelling out an astonishing five year, $27.5 million deal. Quickly people criticized the size of the deal. Especially since Bolland had never scored more than 37 points in a season. Bolland never really got an opportunity to justify his huge price tag because his time in Sunrise, Florida was plagued by injuries.
Over two seasons Bolland only played in 78 games much to the frustration of Panthers fans and played his last professional game in 2015. His contract was traded to Arizona in 2017 for draft picks. The fact that Florida management felt comfortable giving such a big contract to a player coming off a 12 point season in 2013/14 is still a mystery. ‘The Rat’ got caught in a trap early and was unable to bug opponents like had done in the Windy City.
10. Roberto Luongo
As a Canucks fan, I feel I have to bring this one up. Purely because years later it is still an ongoing issue for us. Roberto Luongo was always a tremendous talent and Vancouver owed a lot of him. A star from the very beginning during his time with the Islanders and Panthers, Luongo was a great capture for the Canucks. In 2009, he inked a 12-year $64 million contract. As time went on, this contract became more and more of a major issue. The emergence of Cory Schneider and then Eddie Lack (yes, I know!) relegated their former captain and star to bench and twitter duty.
Getting out of this jam still hasn’t been fully resolved as Luongo high price contract and no-trade clause proved to be a major headache for management. “My contract sucks!” Luongo said mournfully and until 2013/14 Canucks fans cursed under their breath. Finally, he waived his no-trade clause which sent him back to Florida for Jacob Markstrom and Shawn Matthias. However, the Canucks still agreed to pay 15% of his salary. When he retired in 2019, Vancouver was still stuck with paying the remaining three years of his contract. The $3 million per year we are forced to shell out shows how poorly Vancouver handled this deal.
Honourable Mention: Derek Sanderson
This contract won’t make the official list as it is not an NHL contract. However, it deserves mentioning because of the size and how disastrous it was. Derek Sanderson was a key component of the Boston Bruins in the mid-’60s and early ’70s. He famously provided the assist for Bobby Orr‘s ‘Superman celebration in the 1970 Stanley Cup Finals. A big celebrity in Boston and known for his party lifestyle, Sanderson had designs on being a premier athlete.
In 1972, he made the astonishing decision to move to the World Hockey Association. The Philadelphia Blazers paid Sanderson a then-record $2.6 million contract. This made him the highest-paid athlete in the world. Tragically this did not kick start the WHA and the move was a major disaster. Injuries limited Sanderson to just eight games and six points. Faced with a big-time flop, the Blazer decided to get rid of their superstar. Sanderson was paid $1 million to end his contract and re-sign with Boston. His career never truly recovered as alcohol and drug addictions spoiled what was a promising career.
I don’t know how you don’t look at Jeff Skinner as the worst contract of all time. Even, last year, at the writing of this article his production was massively under performing. $9 million for that???