Edmonton Oilers 15 Worst Contracts (2005-2022)

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. Next summer it may even be expanded to top 20. The book is still available on Amazon, though some of the stats on active contracts are now out of date.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.

My latest book The Hockey Economist’s Betting Prospectus is now available. It's a comprehensive commentary on the last 3 years of hockey betting, broken down by team, by category, by strategy, by season. There is plenty of useful information for bettors of all skill levels. It covers pre-pandemic, peak-pandemic, post-pandemic. What worked, what failed. Lessons learned, market trends, team-by-team analysis. What impact did the pandemic have on hockey betting? The market differences between these 3 seasons are discussed at length, and there's a lot to talk about. To read more, visit the Amazon store.
 
Enjoy! Please note: The formatting on the graphics got scrambled being copied from Excel into Google Blogger. It's among the reasons my blog is looking for a new home.

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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 a few more years. The McDavid window is still wide-open, making this a more desirable free agent destination.
 
 
1. Milan Lucic

Signed By:	Peter Chiarelli		Position:	F
Date:	2016-07-01		Age July 1st:	28
Term:	7 years		Playoff GP:	31
Total Money:	$42M		Playoff PTS:	9
Cap Hit:	$6M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	43.8	449	168	648
Per 82 GP	6.3	82	31	118	14.3

"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

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
 

Signed By:	Kevin Lowe		Position:	D
Date:	2007-07-12		Age July 1st:	30
Term:	5 years		Playoff GP:	0
Total Money:	$27M		Playoff PTS:	0
Cap Hit:	$5.4M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	39.0	144	76	452
Per 82 GP	7.8	82	43	257	24.2

"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.”

- Kevin Lowe

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
 

Signed By:	Ken Holland		Position:	D
Date:	2021-08-06		Age July 1st:	27
Term:	8 years		Playoff GP:	0
Total Money:	$74M		Playoff PTS:	0
Cap Hit:	$9.25M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	74.0	0	0	0
Per 82 GP	9.3	0	0	0	0.0

"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.”

-Darnell Nurse

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 can 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. Shawn Horcoff
 

Signed By:	Kevin Lowe		Position:	F
Date:	2008-07-16		Age July 1st:	30
Term:	6 years		Playoff GP:	6
Total Money:	$33M		Playoff PTS:	6
Cap Hit:	$5.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	43.4	389	158	515
Per 82 GP	7.2	82	33	109	16.6

"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.”

– Kevin Lowe

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.
 
 
5. Mark Fayne
 

Signed By:	Craig MacTavish		Position:	D
Date:	2014-07-01		Age July 1st:	27
Term:	4 years		Playoff GP:	0
Total Money:	$14.5M		Playoff PTS:	0
Cap Hit:	$3.6M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	16.6	147	17	143
Per 82 GP	4.2	82	9	80	17.1

“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.”

– Craig MacTavish

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.
 
 
6. Nikolai Khabibulin
 

Signed By:	Steve Tambellini		Position:	G
Date:	2009-07-01		Age July 1st:	36
Term:	4 years		Playoff Wins:	0
Total Money:	$15M		Playoff SV%:	0.000
Cap Hit:	$3.75M		Stanley Cups:	0

 

	Avg Adj Cap Hit	GP	W	GAA	SV%
Total	5.1	117	33	3.00	0.903

"The Edmonton Oilers made such a big commitment. There weren't too many opportunities with such a long term out there"

– Nikolai Khabibulin

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. Benoit Pouliot
 

Signed By:	Craig MacTavish		Position:	F
Date:	2014-07-01		Age July 1st:	27
Term:	5 years		Playoff GP:	13
Total Money:	$20M		Playoff PTS:	0
Cap Hit:	$4M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	22.5	180	84	291
Per 82 GP	4.5	82	38	133	15.5

“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

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.
 
 
8. Nikita Nikitin
 

Signed By:	Craig MacTavish		Position:	D
Date:	2014-06-25		Age July 1st:	28
Term:	2 years		Playoff GP:	0
Total Money:	$9M		Playoff PTS:	0
Cap Hit:	$4.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	10.6	53	11	92
Per 82 GP	5.3	82	17	142	18.6

“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”

– Craig MacTavish

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.
 
 
9. Ladislav Smid
 

Signed By:	Steve Tambellini		Position:	D
Date:	2013-04-01		Age July 1st:	27
Term:	4 years		Playoff GP:	0
Total Money:	$14M		Playoff PTS:	0
Cap Hit:	$3.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	16.7	126	9	73
Per 82 GP	4.2	82	6	48	16.0

"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."

– Jay Feaster

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.
 
 
10. Andrej Sekera
 

Signed By:	Peter Chiarelli		Position:	D
Date:	2015-07-01		Age July 1st:	29
Term:	6 years		Playoff GP:	11
Total Money:	$33M		Playoff PTS:	3
Cap Hit:	$5.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	35.5	221	77	347
Per 82 GP	5.9	82	29	129	20.2

"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."

– Peter Chiarelli

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.
 
 
11. Zack Kassian
 

Signed By:	Ken Holland		Position:	F
Date:	2020-01-29		Age July 1st:	29
Term:	4 years		Playoff GP:	20
Total Money:	$12.8M		Playoff PTS:	6
Cap Hit:	$3.2M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	12.9	85	24	76
Per 82 GP	3.2	82	23	73	11.8

“I don’t think Tkachuk realizes that we’re in the same division and I have a great memory.”

– Zack Kassian

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.
 
 
12. Boyd Gordon
 

Signed By:	Craig MacTavish		Position:	F
Date:	2013-07-05		Age July 1st:	29
Term:	3 years		Playoff GP:	0
Total Money:	$9M		Playoff PTS:	0
Cap Hit:	$3M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	10.9	207	38	198
Per 82 GP	3.6	82	15	78	13.5

"We know what we're getting. I don't think much has changed in his game."

– Coyotes GM Don Maloney

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 Phoenix Arizona Coyotes for another bad contract in Lauri Korpikoski. Gordon scored 4 PTS in 65 GP for the Coyotes.
 
 
13. Andrew Ference
 

Signed By:	Craig MacTavish		Position:	D
Date:	2013-07-05		Age July 1st:	34
Term:	4 years		Playoff GP:	0
Total Money:	$13M		Playoff PTS:	0
Cap Hit:	$3.25M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	15.5	147	32	139
Per 82 GP	3.9	82	18	78	19.7

"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"

– Craig MacTavish

Andrew Ference was an Edmonton boy who returned home on July 5^th 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.
 
 
14. Kris Russell
 

Signed By:	Peter Chiarelli		Position:	D
Date:	2017-06-23		Age July 1st:	30
Term:	4 years		Playoff GP:	1
Total Money:	$16M		Playoff PTS:	0
Cap Hit:	$4M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	16.6	240	55	239
Per 82 GP	4.2	82	19	82	18.9

"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."

– Peter Chiarelli

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.
 
 
15. Mikko Koskinen
 

Signed By:	Peter Chiarelli		Position:	G
Date:	2019-01-21		Age July 1st:	30
Term:	3 years		Playoff Wins:	0
Total Money:	$13.5M		Playoff SV%:	0.897
Cap Hit:	$4.5M		Stanley Cups:	0

 

	Avg Adj Cap Hit	GP	W	GAA	SV%
Total	4.6	109	58	3.00	0.907

"Mikko has a lot of experience as a No.1 goalie and has performed well both internationally and for our club"

– Peter Chiarelli

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.