Being the General Manager of the Edmonton Oilers is not an easy job. Most of the people who have filled those shoes since their days of Stanley Cup glory have failed miserably. Was every GM just a bad choice? Or does being the northern most city in the NHL inhibit effective/efficient free agent recruitment? Peter Chiarelli made some marvelous moves in taking Boston to a Stanley Cup, then took the Edmonton job and fell flat on his face. Edmonton was supposed to be one of the small markets that would benefit from spending restrictions thrust upon the big markets, and never parlayed that into parity.
Craig MacTavish’s name barely appears on the Oilers best contracts list, but is the largest shareholder in the blunder catalogue. The good news for Oilers fans is that they have two of the league’s best players locked into bargain contracts for at least another year. The McDavid window is still wide-open, making this a more desirable free agent destination. Granted, luring Jack Campbell to that suddenly desirable situation immediately back-fired. The Oilers have among the worst lists (#6) as you can see on the rankings report card below. They also rank 29th in PTS per 60 (their best list was #1 in that category). If they win the Cup, Nurse will have to be removed (Campbell would need to play playoff games to earn removal).
This was originally published in my 2020 book The Definitive Guide to Salary Mismanagement, and has now been updated with new contracts. I will continue to update each team’s list every summer going forward. The rule is that only active contracts can move up or down. Expired deals cannot pass each other (with a few exceptions). The book is still available on Amazon, though some of the stats on active contracts are now out of date. You may yet find it interesting because there were detailed stat graphics that you won't find here. One thing you won't find here are entry level contracts because they all come from the same cookie cutter and require less skill at the negotiating table.
Updated June 28, 2024: Adjusted for $88M cap and updated stats for Nurse and Campbell with no change in the order.
1. Milan Lucic
Adjusted Cap Hit: $46.8M, $6.7M (avg)
Value Returned: $15.5M, $2.2M (avg)
% Earned: 33%
"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.
2. Sheldon Souray
Adjusted Cap Hit: $41.6M, $8.3M (avg)
Value Returned: $18.9M, $3.8M (avg)
% Earned: 45%
"Yeah, there are some players that don't necessarily want to play in Edmonton, but I think those players have other markets they wouldn't want to play in as well.”
Edmonton landed Sheldon Souray as one of the big prizes on the 2007 UFA market at age 30, but wasn’t inked until 2 weeks into the frenzy. Roman Hamrlik had agreed to similar terms in Montreal 10 days earlier. 6 games into his Oilers career Souray suffered a major shoulder injury in a fight that cost him 55 games. He successfully recovered with an impressive 53-point campaign that included 23 goals and 268 shots.
The injury bug struck again the following year, as a concussion and broken hand landed him on IR for a majority of the season. Sheldon emerged from that with a grievance about how the Oilers handled his injuries and was subsequently demoted to the AHL, where he played for one season before being bought out.
3. Darnell Nurse
Adjusted Cap Hit: $75.1M, $9.4M (avg)
Value Returned: $35.7M, $4.5M (avg)
% Earned: 48%
"I think any time that you have a team and a management group that believes in you like our team in Edmonton does, it always feels good.”
If you read my summary of Darnell Nurse’s previous bridge deal on the Oilers best contracts list, that provides a hypothesis of how he eventually received $74M. You should read that before reading this. Ken Holland may very well have been willing to give his best defenseman an expensive long-term extension 2 years earlier, they just didn’t have the cap space to meet the asking price. Nurse scored above a 50-point pace in the pandemic shortened 2021 season, beating his previous career high by 12 PTS against a defensively porous Canadian division. That stat line was worth approximately $8.5M in expected salary. So, $9.25M isn’t a reach, at least if you believed that level of offensive output was sustainable.
One season later, before this contract had even begun, Nurse regressed into a $7M player. It seems that 50 PTS was a fluke, and you could expect about 40 PTS going forward. There are some other intangibles like toughness and physical play that increase his worth, but there has to be some concern about the sustainability of the whole package into his mid 30s. At the right price, every GM in the league would love to have this guy. Sadly, he’s at least $2M above “the right price” and that disparity is at risk of growing even larger as this progresses. Maybe they are paying him too much, but they unquestionably would have been a worse team had he left in free agency.
4. Jack Campbell
Adjusted Cap Hit: $25.1M, $5.0M (avg)
Value Returned: $10.0M, $2.0M (avg)
% Earned: 40%
Nothing stings more than a hard whiff on a big UFA goalie contract that turns awful immediately. No honeymoon period, no enjoying the new toy, just 100% brutality from day one. That’s what Edmonton received in Jack Campbell, who couldn’t stop a beach ball from the start. Jack dropped from a .911 SV% with Toronto down to .888 with the Oilers. Evidently the defensive system in Toronto had something to do with his success as a Leaf, and his play completely collapsed upon arrival in Edmonton. According to goalie guru Kevin Woodley, the type of shots that give Campbell trouble was not a strength of the Oilers defense, and had the right expert taken a look at the numbers, this disaster could have been avoided. 3.5 years still remain (at the date I’m posting this) and its not impossible that he figures out and repairs the problem, but if that happens, I’ll demote this deal further down the list, and in the even less likely even that he carries them to a championship or wins the Vezina, it will be removed entirely. He’s currently in the AHL working on a solution.
5. Shawn Horcoff
Adjusted Cap Hit: $46.5M, $7.7M (avg)
Value Returned: $19.0M, $3.2M (avg)
% Earned: 41%
"Having him under contract long-term is something that has been on our radar for a long time and we are extremely pleased to finalize this deal.”
Shawn Horcoff had just scored 50 PTS in 53 GP in 2008 at age 28 in a season cut short by injury when Kevin Lowe secured his autograph on a 6-year extension that wouldn’t start until after his 30th birthday. The negative growth in his output started immediately. We never got to find out what he might have solicited on the open market, but I’m still comfortable declaring this an overpayment. Mike Riberiro had just signed a similar deal a few months earlier in the middle of an 83-point season.
Shawn would only top 30 PTS twice in six years, finishing with an average of 33 PTS per 82 GP at the price point of a 70-point player. Eventually Horcoff was shipped out of town for Phillip Larsen and a 7th round pick with 2 years remaining, going to Dallas where his ice time was slashed.
6. Nikolai Khabibulin
Adjusted Cap Hit: $22.0M, $5.5M (avg)
Value Returned: $5.3M, $1.9M (avg)
% Earned: 34%
"The Edmonton Oilers made such a big commitment. There weren't too many opportunities with such a long term out there"
At age 36, Nikolai Khabibulin was no longer the goalie who had won the Stanley Cup with Tampa. His stint in Chicago was mostly a failure, but managed to play some good hockey in the final year, such that enough General Managers were surely interested in soliciting his autograph on a new deal. There had to be plenty of offers with a similar salary, but none that went 4 years expiring at age 40. Tim Thomas had elicited a 4-year term from Boston at age 35 a few months earlier, but he was about to win the Vezina trophy.
Nikolai ran into injury issues in year one, derailed by surgery to repair a herniated disc. When he returned the following season, he was demonstrably bad and would eventually be overtaken as the starter by Devan Dubnyk. On the bright side, he did help the team secure 3 consecutive first overall draft picks, so perhaps this wasn’t quite so bad after all. If they brought him in for his playoff experience, it was irrelevant, as he backstopped them to zero playoff appearances.
7. Mark Fayne
Adjusted Cap Hit: $17.9M, $4.5M (avg)
Value Returned: $4.2M, $1.0M (avg)
% Earned: 23%
“We made a case for our situation here in Edmonton. It was a compelling story for them, as it was for me to tell. The situation is improving here, in spite of the fact that the results have lagged, but it was a compelling enough situation that at the end of the day we were able to quickly react to these players.”
The Oilers knew they weren’t acquiring offensive production when they signed Mark Fayne, but they had to at least be expecting an NHL defenseman for that kind of dough, the same terms received by Nicklas Grossman 2 years earlier. Fayne only lasted 2 years before being demoted to the minors, putting up decent numbers with the Bakersfield Condors in year three.
By year four Mark was completely out of the NHL, and he has not played pro hockey since this agreement expired. He was unable to crack the Oilers roster at a time when they were desperate for decent defensemen. Management preferred to eat the sunk cost in the minors.
8. Benoit Pouliot
Adjusted Cap Hit: $24.2M, $4.5M (avg)
Value Returned: $4.2M, $1.0M (avg)
% Earned: 43%
“Pouliot was our most important addition because we needed someone with speed. We talked about size, we talked about increasing our competitiveness and he’s a guy who tracks the puck very well and pressures the puck very well. He’s a great skater and we really felt we needed to add that element.”
Craig MacTavish might have understood that what he offered Benoit Pouliot was 40% more than what you’re supposed to pay a 30ish point player, but if you want to lure free agents to Edmonton, you have no choice but to overpay. Or maybe he was expecting the 27-year-old winger to evolve into a more productive player.
The team gave Benoit every opportunity to succeed over the first two years, posting the two highest average ice times of his career. By year three, the balloon popped, producing just 14 PTS in 67 GP with a big ZERO PTS in 13 playoff games before being bought out. Pouliot played 1 more season for a little over $1M before retiring.
9. Nikita Nikitin
Adjusted Cap Hit: $11.4M, $5.7M (avg)
Value Returned: $3.2M, $1.6M (avg)
% Earned: 28%
“Nikita was playing better, he started off slowly, I don’t think he was in the best shape that he could have been, we have to get that rectified next year”
The Blue Jackets gave the Oilers permission to negotiate a new contract with Nikitin before he was set to hit the UFA market, then traded his rights for a 5th round pick after an agreement was reached. MacTavish paid an exorbitant sum to acquire a 3rd pairing defenseman, and the harsh criticism of the acquisition began the day it was signed.
Needless to say, the experiment did not go according to plan, as they got just 53 NHL games, and an overpriced defenseman for their farm team. Although he is NOT the most expensive defenseman in Oilers farm team history. Nikita returned to Russia at the conclusion of this accord, marking the end of his North American career.
10. Ladislav Smid
Adjusted Cap Hit: $18.0M, $4.5M (avg)
Value Returned: $3.9M, $1.0M (avg)
% Earned: 22%
"We feel he’s a guy who can come in and play big minutes. He’s a guy who can kill penalties and gives the coaching staff options."
Ladislav Smid had played 7 seasons for the Oilers, never scoring more than 15 PTS in a season, mostly just piling up hits and blocks. The Czech defenseman was a few months away from unrestricted free agency when Steve Tambellini made him this generous offer.
Smid only played 17 games with the Oilers under this treaty, as he was traded to the division rival Calgary Flames for a prospect (who only played 2 more games in the NHL) and a future back-up goalie. Ladislav played 126 games and scored 9 PTS. A back injury did contribute to the decline, but he also missed a big chunk of time as a healthy scratch.
11. Andrej Sekera
Adjusted Cap Hit: $38.0M, $6.3M (avg)
Value Returned: $14.8M, $2.4M (avg)
% Earned: 39%
"He's a very smart player, strong player. He can log a lot of minutes. He can defend. He can play your power play, very versatile."
The early months of Peter Chiarelli’s reign in Edmonton was met with boundless optimism, when he drafted Connor McDavid then signed Andrej Sekera and Cam Talbot within the span of a week. The commentary from pundits was largely positive when the 29-year-old Sekera inked a 6-year ticket and they were mostly proven right over the first two seasons as this investment yielded a respectable return, helping the Oilers earn a rare playoff appearance.
That’s where the good news came to a crashing halt as he tore his ACL in the second round and was never the same player, leading to a buyout in the summer of 2019. Would this have turned out to be a good contract had that ACL never torn? It’s entirely possible and he was a candidate for injury exemption, but there was still significant risk handing out a contract that would not expire until age 35. The risk of decline on the back half was already high. Andrej went on to sign a 1-year deal with Dallas at a fraction of his previous salary.
12. Zack Kassian
Adjusted Cap Hit: $13.6M, $3.4M (avg)
Value Returned: $3.2M, $0.80M (avg)
% Earned: 23%
“I don’t think Tkachuk realizes that we’re in the same division and I have a great memory.”
The only season when Zack Kassian came even close to earning $3.2M was 2019/20, when he scored at a 47-point pace playing on a line with McDavid and Draisaitl. There are a lot of minor leaguers who could approach that level of production playing that many minutes with two of the league’s best players. It just so happens; Zack signed this extension in the middle of that campaign. At the time, the battle of Alberta was a raging inferno, and Kassian was feuding with Matt Tkachuk. Surely that helped inspire Holland that they needed his toughness now more than ever. Kassian stoking the fire in that rivalry helped him make $13M.
Then in 2021, he was booted off the McDavid line, and scored 5 PTS in 27 GP which was worth about $750K. Basically, McDavid made him rich and this pact became almost instantly regrettable. His 2021/22 season wasn’t much better, as he continued playing at a sub $1M level. Afterwards, the Oilers desperate to clear cap space had to trade draft picks to dump the contract on Arizona.
13. Boyd Gordon
Adjusted Cap Hit: $11.8M, $3.9M (avg)
Value Returned: $3.3M, $1.1M (avg)
% Earned: 28%
"We know what we're getting. I don't think much has changed in his game."
In the six years prior to signing with the Edmonton Oilers, Boyd Gordon had not surpassed 23 PTS in a season, yet for some strange reason they paid him like a 40-point producer. Chris Kelly and Kyle Brodziak had received similar deals in the previous year after producing much higher point totals. We shouldn’t be shocked that the Oilers had to pay a premium to lure this UFA to northern Alberta, as that seems to be the common theme emerging from this list.
Gordon did produce 8 goals and 21 PTS in year one and 13 PTS in year two before Boyd was bounced to the Arizona Coyotes for another bad contract in Lauri Korpikoski. Gordon scored 4 PTS in 65 GP for the Coyotes.
14. Andrew Ference
Adjusted Cap Hit: $16.8M, $4.2M (avg)
Value Returned: $7.7M, $1.9M (avg)
% Earned: 46%
"Andrew Ference is a really big piece for us. Our depth on defence we have substantially improved. I've had my eye on him all year thinking he would be a perfect fit for our group"
Andrew Ference was an Edmonton boy who returned home on July 5th 2013 at age 34, two years removed from winning the Stanley Cup with Boston. The Oilers were still trying to fill the void left by Chris Pronger, and Mac T really believed this was the solution, with the playoff drought at 7 years and counting. Ference was even named team Captain before he’d ever played a game in an Oilers jersey.
They laid a heavy burden on his aging shoulders in year one, playing him over 21 minutes per game (higher than his previous 4 seasons with the Bruins), but it was a downhill journey after that. It soon would become clear that he was no longer the same player and that Father Time had nailed him with a heavy hip check. By year three, he lost the “C” when the team started making him a regular healthy scratch. Ference only played 6 games before he suffered a hip injury in January, ostensibly ending his career.
Ference later confessed that the suffered an abdominal injury in Boston that was believed to have caused the hip issue. Mac T might have bought damaged goods, which wasn’t necessarily diagnosable by Edmonton physicians at the time of purchase.
15. Kris Russell
Adjusted Cap Hit: $17.8M, $4.5M (avg)
Value Returned: $9.2M, $2.3M (avg)
% Earned: 52%
"I want to have Kris back. I thought he was really good for our team the way he approaches the game, the way he battles, his poise, his skating."
Kris Russell was one week away from a return trip to the UFA market at age 30 when Peter Chiarelli decided to lock him up for a further 4 years. Russell had never been much of an offensive defenseman (peaking at 34 PTS in 2015), gaining most of his notoriety for evolving into a shot blocking specialist.
If you play in a fantasy hockey format that counts blocked shots, you might think I’m crazy for ranking this among their worst contracts (his 223 blocks in 2018 helped me win a championship in a very deep and competitive league). There may be a price where that kind of skill brings some value, but it’s substantially less than $4M. When his ice time plunged to 16.8 minutes per game in year three, he became mostly useless even to those of us who coveted those blocked shots.
16. Mikko Koskinen
Adjusted Cap Hit: $14.6M, $4.9M (avg)
Value Returned: $11.0M, $3.7M (avg)
% Earned: 75%
"Mikko has a lot of experience as a No.1 goalie and has performed well both internationally and for our club"
Mikko Koskinen had very little experience as a No. 1 goalie in the NHL when Peter Chiarelli decided to roll the dice with a 3-year extension. This was heavily scrutinized in the media and was a major catalyst in the firing of Chiarelli shortly thereafter. Frankly, by the time it was done it wasn't an outrageous price to pay for a 1B goaltender, finishing with a .907 SV%. But history will always remember it as terrible because it got the GM axed so quickly after it was signed. Koskinen left the NHL to play in Switzerland when this was done.
17. Steve Staois
Adjusted Cap Hit: $17.1M, $4.3M (avg)
Value Returned: $9.7M, $2.4M (avg)
% Earned: 57%
"Steve exemplifies what it means to be an Edmonton Oiler and we couldn't be happier with this long-term extension"
Steve Staios had enjoyed a long NHL career with over 600 games played and had been with the Oilers since 2001. The veteran defenseman had scored 28 PTS in 2006, plus an additional 6 PTS in 24 playoff games, before inking this 4-year pact the following November at age 33. The Oilers blueline was still reeling from the loss of Chris Pronger, so making this commitment to a gritty defender probably made perfectly logical sense to Kevin Lowe, hoping to stabilize a massive problem (Daniel Tjarnqvist was their leading defenseman in average ice time that year, Marc-Andre Bergeron their top scoring D). Steve suffered a serious knee injury 2 days after this was signed, which later required surgery.
Staois peaked in ice time at 22 minutes in year one, but that also started a downward trend that finished with 14.7 minutes per game in year four. The offense was much lower than 2006, averaging 16 PTS per 82. The Oilers were able to unload him on Calgary for a 3rd round pick before it expired. Steve didn’t do much for the Flames, which might have been part of the reason Lowe was willing to ship him to a division rival.
18. Nail Yakupov
Adjusted Cap Hit: $6.2M, $3.1M (avg)
Value Returned: $2.4M, $1.2M (avg)
% Earned: 39%
“Our growth is going to be internal, incremental growth, and Yak is a by-product of that strategy. There was a lot of discussion around Yak about the potential to trade him, and again I’ve said, it’s not my preference or is it good strategy to trade developing players. So he’s been rewarded with a two-year contract.”
It was becoming apparent by the end of Yakupov’s ELC that he was a bust as a 1st overall draft pick, such that the Oilers were able to procure his signature on 2-year bridge deal at a wildly smaller price that your average first overall pick. Nail dropped to 23 PTS in 60 GP in year one, but the St. Louis Blues were still willing to gamble that there was untapped upside, trading a 3rd round pick to acquire the Russian winger.
That’s where this venture turned especially sour, as Yaks dropped to a 4th line depth player who scored 9 PTS in 40 GP. Players who are terrible defensively generally don’t make good 4th liners. Over 2 seasons he played 100 games and scored just 32 PTS, arguably the worst 1st overall pick since Patrick Stefan. He would ink one more cheap deal with the Colorado Avalanche, where he scored 16 PTS in 58 GP. That was the “nail in the coffin” for his NHL career, as he left for Russia in the summer of 2018.
19. Fernando Pisani
Adjusted Cap Hit: $17.0M, $4.3M (avg)
Value Returned: $6.7M, $1.7M (avg)
% Earned: 39%
"We are very concerned about Fernando's medical condition and we wish him nothing but a full and healthy recovery"
Fernando Pisani had reached cult hero status in Edmonton in July 2006 after leading the playoffs in goals, including 5 game winners. The winger was a late bloomer who had only logged 2 full seasons in the NHL by age 29, and was paid nearly double what his statistics/experience warranted.
In the first year of his new deal (as he was turning 30 years old), Pisani’s scoring output dropped by nearly 10 PTS despite a significant increase in ice time. By year two, Pisani was diagnosed with colitis and missed a chunk of the season. Injuries would continue to dog Fernando until this expired, and he was considered for injury exemption. Unfortunately, he was overpaid from day one and was performing well below his pay grade even when healthy. Had the injuries never happened, this would have ranked higher up the list.
20. Kailer Yamamoto
Adjusted Cap Hit: $6.5M, $3.3M (avg)
Value Returned: $2.7M, $1.4M (avg)
% Earned: 42%
The Edmonton Oilers thought they were buying a 40-point player when they reached this agreement with Kailer Yamamoto, but he regressed to a 35-point scorer in year one, prompting the team to ship him off to Detroit for a buyout. All things considered, he was not too far off the production you’d expect from this pay grade, but the team is under such difficult cap constraints that overpaying even by a little bit was deemed unacceptable. It didn’t take long for Seattle to sign him for half the price, where it’s entirely plausible he gets back on track.