Historical Worst NHL Contracts:
What were the worst contracts in the NHL each year of the salary cap era? Scroll down and find out. Or you can scroll down even further to see the worst 10 contracts of the salary era list that I made back in 2020 after publishing my book on the subject. The contents of my first two books will be posted for free on my blog during the 2022/23 season to promote my new book.
2022: Winner: Erik Karlsson, runner-up: Marc-Edouard Vlasic
2021: Winner: Erik Karlsson, runner-up: Jeff Skinner
2020: Winner: Marc-Edouard Vlasic, runner-up: Brent Seabrook
2019: Winner: Milan Lucic, runner-up: Brent Seabrook
2018: Winner: Zach Parise, runner-up: Bobby Ryan
2017: Winner: Bobby Ryan, runner-up: Zach Parise
2016: Winner: Andrew Ladd, runner-up: Zach Parise
2015: Winner: David Clarkson, runner-up: Nathan Horton
2014: Winner: David Clarkson, runner-up: Jordan Staal
2013: Winner: Roberto Luongo, runner-up: James Wisniewski
2012: Winner: Vincent LeCavalier, runner-up: Scott Gomez
2011: Winner: Vincent LeCavalier, runner-up: Wade Redden
2010: Winner: Chris Drury, runner-up: Scott Gomez
2009: Winner: Chris Drury, runner-up: Scott Gomez
2008: Winner: Rick DiPietro, runner-up: Chris Drury
2007: Winner: Nikolai Khabibulin, runner-up: Derian Hatcher
2006: Winner: Nikolai Khabibulin, runner-up: Glen Murray
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What have been the worst 10 NHL contracts signed since the salary cap was introduced in 2005? The following has been clipped from my latest book "The Definitive Guide to Salary Cap Management", which outlines all the worst deals that each NHL team inked in the last 15 years.
“This is a great day
for all Lightning fans.”
Vincent Lecavalier notched 40 goals and 92 PTS in 2008 and was a year from unrestricted agency when the Lightning locked him up with this massive 11-year extension. Former player agent Brian Lawton had been officially hired as VP of Hockey Operations a month earlier, prompting Jay Feaster to quit as General Manager 2 days before this was signed, claiming Lawton and the owners were running the team and his services were no longer required. Lawton was named Feaster’s successor, and made his first big splash with this pact.
If the Lecavalier contract was a specific point of contention that contributed to Feaster’s departure, he would eventually get the last laugh, as it started turning sour before it even had a chance to start. The star dropped from 92 PTS in 2008 down to 67 PTS in 2009. Vinny’s days as an elite goal producer were formally behind him and struggled to stay healthy after turning 30, which is a risk when giving an 11-year contract to a 29-year-old. Over 4 seasons, the center scored at a 67-point rate before Tampa used a compliance buyout to escape this liability.
Vinny landed on his feet, procuring another generous sum of money from the Flyers that you can read about on their worst contracts list. Don’t feel bad for Vinny though, he’ll continue getting $2M+ pay cheques from the Lightning until 2027. Scientists will have cloned dinosaurs before Vinny stops banking that Tampa money.
"In all of our discussions with Rick, he made it clear that he
wanted to be an Islander for the rest of his career, but it was of equal
importance to Rick that we work out a deal that would allow us to continue to
build a Stanley Cup contender for years to come. This deal is great news for
our franchise and our fans."
When Garth Snow signed Rick DiPietro to this 15-year contract in 2006, it sent shockwaves through the hockey world. Regardless of how it would eventually play out, credit Garth for his creativity. This was a minor coup in salary cap circumvention, as nobody had yet conceived the notion of signing free agents to a ridiculously long term in order to get the cap hit down. Unlike the “back-diving” revolution this inspired, DiPietro did not get his agreement front loaded (Mike Richards got a slight back-dive in 2007, then Lecavalier got a full back-dive in 2008).
It could be argued that this contract is only bad because DiPietro couldn’t stay healthy. The success of this investment would have been different had DiPietro been able to sustain a high level of goaltending. The former 1st overall draft pick was mostly a league average goaltender for 63 GP the season prior, posting a 3.02 GAA and .900 SV%. He was eventually bought out, but don’t feel bad for Ricky…he’ll be getting $1.5M per year from the Islanders until 2029. Humans will be flying around in starships, he’ll still be cashing Islanders pay cheques.
“31-year-old Wade
Redden, a reasonably dependable puck-moving defenseman who had a dreadful
2007-08 in Ottawa and has never been regarded as a game-changer over 11 seasons
with the Senators.”
On July 1st 2008, the two top defensemen available on the free agent market were Wade Redden and Brian Campbell, with the latter having a higher offensive ceiling. Campbell rightfully landed the bigger pay day, but Redden was not far behind. A big difference between the pair was that Wade was 2 years older, as Sather was taking an enormous risk signing a 31-year-old to a 6-year term. The GM surely drew inspiration from the 6-year extension Dan Boyle had signed a few months earlier for the same wage at the same age.
While Boyle would age gracefully, Redden would not. He dropped from 38 PTS down to 26 PTS in year one, spiralling further down to 14 PTS in year two before getting demoted to the AHL. Eventually Redden was bought out. Correct me if I’m wrong, but Wade Redden should be the highest paid player in AHL history (injury rehabs notwithstanding). I sure hope he paid for every single road meal that AHL team ate.
“I know he left a lot
of money on the table by accepting the offer we made to him. There were people
that were offering a lot more than we were.”
As free agency neared in 2011, Glen Sather convinced his owner to buy out the remainder of Chris Drury’s contract to make room to take a big run at 31-year-old Brad Richards following a 77-point campaign. Glen won the bidding with $60M, claiming afterwards that other teams were offering “a lot” more money. Giving a 9-year term to a player at this age was insane, but the salary was front loaded in such a way that he could retire after 6 seasons, helping lower the cap hit.
Richards was quasi productive for the first two years then dropped to 50 PTS in year three at age 33 and was bought out. This is among the most expensive buyouts in NHL salary cap history, but was a CBA amnesty buyout that would not count against their future cap. Brad’s lucrative “Golden Parachute” would pay him million dollar cheques until 2026.
“You guys just here
to blame someone. You never look yourselves in the mirror, eh? You're always
good. You never make the mistakes. Your articles are always perfect. In
reality, what have you done for this city? If you ask yourself, what have you
done besides only criticize? Not much.”
“I am who I am. Life
is too beautiful to be sad, to be depressed. The sun comes up every day and
it's beautiful.”
Ilya Bryzgalov had been in the Vezina trophy conversation for the previous 2 seasons (78 wins + 35 goals saved above average) before reaching the open UFA market for the first time at age 31. The Flyers won the bidding process, though you’ll never hear anyone involved in this debacle claim victory. The Flyers opted to offer a ridiculous 9-year term that would take him to his 40th birthday in an attempt to lower his annual cap hit. Year one was almost average, posting 38 wins, 16 losses with a 2.48 GAA and .909 SV%, which was borderline decent for his compensation rate (that was before posting an .887 SV% in 11 playoff games).
By year two, his play had eroded further, and his relationship with the Philadelphia media became contentious. After 99 regular season GP with -20 goals allowed below average, management decided to pull the plug, using one of their compliance buyouts afforded by the new CBA. They did not want to risk this situation spiraling any further down the toilet bowl. But you don’t need to feel bad for Ilya, he’ll be collecting $1.6M per year until 2027. Elon Musk will be walking around on Mars before Ilya’s Flyers cheques stop coming…
"It's pretty
exciting. We ranked them both as number ones, and we never expected to get both
of them."
Glen Sather’s desire to pluck Scott Gomez from the New Jersey Devils was two-fold, not only did he want Scott wearing Rangers blue, but he also wanted one of their biggest rivals to be deprived of a key piece to their Stanley Cup championships. It was as much about inflicting pain on an enemy as it was about bolstering his own roster. Gomez had long been a fine player, but paying this much money for a 60-point guy was certifiably insane. Pavel Datsyuk had signed for significantly less money a few months earlier during an 87-point seasons, while Danny Briere’s 95 PTS earned him a smaller salary the same day as Gomez.
Gomez was signed on the same day as Chris Drury (more to come on him), and Sather could not have been happier. Gomez scored 70 PTS in year 1 and thus commenced the diminishing returns. There should be more conspiracy theories about how Sather managed to trade this albatross to Montreal for Ryan McDonagh. Did the Montreal GM lose a bet? Was there blackmail involved? At one point in Montreal, Gomez went over 365 days without scoring a goal. Ouch!
"I promise you
we’ll give it everything we have night in and night out to uphold our end of
the contract."
Bryan Murray had seen one season of Bobby Ryan in Ottawa (70 GP, 48 PTS) before signing the winger to this early extension. That stat line warranted maybe a $5M salary (adjusted for cap inflation), but Murray was forced to overpay to entice Bobby to pass up an opportunity at unrestricted free agency. The team had paid a heavy price to acquire him (Silfverberg and a 1st round pick) and it would have been embarrassing if they lost him to unrestricted free agency 2 years later.
Bobby had some big moments in the 2017 playoffs, but that’s not worth $7.25M AAV…not even close. Bobby won the title of the worst contract in the whole NHL for 2017. He would average 44 PTS per 82 GP over 5 seasons before being bought out, signing a 1-year deal with the Red Wings shortly thereafter.
"I think the
Oilers have been missing a little bit of attitude and a little bit of swagger
over the last couple of years, and that's something that I bring to a team as
well.”
Milan Lucic came to Edmonton as a tough guy with offensive upside who could potentially play with McDavid while also protecting him out on the ice. Milan did flash some of that upside when he potted 50 PTS in year one, but that success proved fleeting, dropping to 34 PTS in year two, 20 PTS in year three. The flaw in the logic behind his acquisition is that he’s far too slow to play with Connor, or even Draisaitl for that matter.
From a production
standpoint, Milan peaked at age 22 and began to decline by age 25. By age 29 he
was washed up and nothing better than a bottom 6 banger who is being paid like
a top 6 guy who can score. Milan was the winner loser of my 2019 Worst NHL Contract
Award. Someway somehow, Ken Holland managed to convince the Flames to take this
deal off their hands in exchange for James Neal. The
Flames were responding to criticism that they lacked toughness in the playoffs,
and over-compensated.
“You can’t just go
pick up a Brent Seabrook. If you don’t have someone like that, to be the
performer that he is on the ice as well as the leader he is off the ice, if you
don’t have Brent, you’re looking for the exact same player. We know what he’s
all about”
Brent Seabrook was a warrior who helped the franchise win 3 Stanley Cups. It’s defensible why Stan Bowman felt this reward was necessary, but giving an 8-year deal to a 31-year-old with all those hard miles on his odometer is bad asset management. Stan should have made Seabrook’s previous contract his last and gone full-term on that treaty instead of 5-years.
Brent was a decent player in season one when he scored 39 PTS, but the depreciation kicked in the following campaign. By year three his ice time dropped under 20 minutes per game and he started becoming a healthy scratch. In year four he suffered a serious injury to his hip, requiring multiple surgeries. The best-case scenario for the organization is for Brent to finish the rest of the contract on “Robidas Island”. The bad news is that it seems like the old vet is determined to resume his career, and is dedicated to making a full recovery.
“At the end of the
day it's not all about money for me. It's about being in a good place for my
family and being on a team that's going to contend every year. You'd be crazy
not to want to be a part of this group and this organization. We'll see what
happens.”
Garth Snow gave a 7-year contract to a 30-year-old player coming off a 46-point season. This turned sour right out of the gate, with Andrew Ladd dropping down to 31 PTS in 78 GP in year one. He’s a good character guy, but it’s never good to see that large of a point decline happen right away, especially at that age when an athlete is less likely to bounce back.
Andrew scored 29 PTS in year two and was in the AHL by year three. This is the greatest contract Kevin Cheveldayoff never signed. Ladd was part of the infamous UFA class of 2016, one of the most astounding collection of calamities in the last 15 years.
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