How did the Edmonton Oilers get this broken?

Wow just wow.  What more can you say about what has happened to the Edmonton Oilers? They seem like a broken group don’t they? The looks on the faces of players, the body language on the ice, the interviews in the dressing room, this group of players is going through a difficult time right now… and no one seems to have an answer as to why?

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Ten years ago. I wrote a piece on 10 things wrong with the Edmonton Oilers (from a fan’s perspective), the number one item on that list was goaltending. Here we are a decade later and goaltending is still an issue.

Where is the team that many predicted would be a serious Cup contender in September? What has happened to the Oilers powerplay that was the best of all-time last season? What has happened to the goal scoring? What happened to surrounding Connor McDavid with a supporting cast that would ensure a championship for the NHL’s most northern team?

At the time of this writing the Edmonton Oilers have five wins in eighteen games. Lots of talk as to where teams are at the US Thanksgiving mark. This is not an applicable guide, but the Oilers are not near a playoff position at this time. In fact, if it will take 95 points to make the post season, the Oilers would have to win 42 out of 66 games just to hit 95 points. Now, it is worth mentioning that the Oilers went on a pretty good streak post American Thanksgiving where they had 40 wins post this mark… so while it might be possible, every loss the Oilers suffer digs them deeper, and makes the odds increasingly more difficult to reach.  The Oilers could be mathematically out of the playoffs by mid-January.

So, what has happened to the Edmonton Oilers and how did they get to where they are today?

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What has broken the Edmonton Oilers?

10. Bad luck – if you have watched an Oilers game this season (and many have difficult to watch) this team is not getting the bounces. Worse yet the opposing teams are. Not to make excuses for the team, but the Oilers have run into hot goaltending, and some broken plays that have resulted in goals for opposing teams. When you are down and out, you tend not to get the breaks or the bounces. Players getting high-sticked in the face with no penalty call, offsides or goalie interference calls that go the wrong way, it sees never ending with this team. The Oilers biggest enemy on a lot of nights is themselves. Two dropped sticks, one that put Zach Hyman in the wrong place at the wrong time, and one that tripped up Philip Broberg, led directly to goals against. This was in one game vs. the Florida Panthers, the Oilers woes can be attributed to some poor luck that they have encountered.

9. Poor Drafting of talent – for years the Oilers drafted the same type of player, fast, but small forwards with offensive potential. Sure, the Oilers had their share of number one overall picks, including the bust of a pick in Nail Yakupov first overall in 2012. The Oilers drafted defense that were supposed puck movers and offensive minded (Evan Bouchard, Philip Broberg et al) instead of big, strong shut-down dee. They failed to secure defensive and goaltending talent. When you have numerous scouts, advisors and analytics teams you would think that you would have a clear understanding of what the needs are and which potential prospects you should be targeting. Case in point, in 2012, everyone was hyping Nail Yakupov, but should that have been a year that the Oilers traded their top selection away? They could have easily traded down and acquired a defenseman. If you recall, in the 2012 NHL Entry Draft eight of the first ten picks were defenseman. Just saying. Here’s some notable defensemen that were selected in the top ten that year:

  • Morgan Rielly went fifth overall
  • Hampus Lindholm went sixth
  • Matt Dumba went seventh
  • Jacob Trouba went ninth

8. Overvaluing of players – the Oilers have a history of over-valuing their players. Therefore, when it comes to trying to make a trade, they often cannot get the return they seek because they are not in a position of wealth when it comes to tradeable assets. Everyone knows they need goaltending support, but who do they have to trade for a serviceable goaltender? You don’t want to (or more accurately should not) trade 97, 29, 93, 18, 14 or 91 so who is left?

7. Competitive Loopholes / the US factor – it’s no secret to observe what teams like the Tampa Bay Lightning (Nikita Kucherov), Vegas Golden Knights (Mark Stone) and Colorado Avalanche (Gabriel Landeskog) have all leveraged, we won’t say cap circumvention, more like “loopholes” to have star players return form injury just before the playoffs (where there is no salary cap). It’s not a coincidence that all three of these teams won the Stanley Cup in recent years. Furthermore, Canadian teams, including the Oilers, face unique challenges such players not wanting to play in Canadian markets, players looking to play in more tax-friendly markets (see Florida, Vegas etc). Canadian-based NHL teams do in fact have it harder than their US-based teams when it comes to securing and retaining talent. The modern era expansion has made it near impossible for a Canadian-based team to win the Stanley Cup. It’s been a staggering 30 years since the Montreal Canadiens were the last Canadian-based Stanley Cup champion. It’s hard to win a Stanley Cup championship, it’s even harder if you are in a Canadian market.

6. Daryl Katz – Daryl Katz seems like a nice enough man, after all he kept the Oilers in Edmonton (although he did make mention of Seattle in a notorious negotiating tactic prior to building the new arena in Edmonton). The Rexall billionaire has been referred to as a bit of a fanboy of the eighties Oilers, and has serviced many of the players from the glory years, the most recent being Paul Coffey. However, in terms of the management teams that he has put together over the past decade, the team has not been able to build a solid Cup contender, and this with being gifted generational talent, Connor McDavid. Ultimately the buck stops with owner Daryl Katz. While not involved in the day to day operations, you have to question his feedback on core moves and the overall direction of this team over the past eight to ten years.

5. Darnell Nurse – again you can’t pin this on one player, but his albatross of a contract is preventing the oilers from picking up other depth players that the team sorely needs. He is owed $9,250,000 per season for the next six years (including this season). This is a gross overpay (and good on his agent for securing this payday), but we’ve seen how these types of contracts handicap teams in the past.  This is no exception. If you factor in the play of this player, a fair price point may have been in the 4.5-5.5M per year range. (Ask some Oilers fans and they will say in the 2-4M range is more accurate). You cannot fault a player for signing an eight year deal valued at $74,000,000 USD. Each and every fan that thinks Darnell Nurse is overpaid (and he is), would have taken the same deal had they been in the same situation. It does have a direct impact on the bottom line that is the salary cap though. You simply cannot have 2-players that make up 30-35% of your payroll/cap. That is not a recipe for success.

4. The Edmonton media – (not all) but there are some media personalities who make it hard for players to play in Edmonton, or even want to come and play in Edmonton. It has been said that over the years that the media in Edmonton (and to a lesser extent some fans) have driven players out of town. Of course, this is anecdotal, as players will not say anything, but the Edmonton media is very critical in a hockey crazy market that was spoiled with five Stanley Cup championships in their first eleven years of existence. We don’t need to mention any names, but the Edmonton media tend to give it to the players, and to a lesser extent coaches pretty good in Edmonton. Negativity breeds negativity and that might just be where the team is right now. Not a lot of happy faces during the media scrums and player availabilities.

3. The NHL salary cap – the frozen cap has not helped a number of teams, but the teams that it has impacted the worst, include the Edmonton Oilers. The flat cap has not allowed the team to acquire the pieces they need to be a true Cup contender.

Here is the current status of the Oilers cap situation (as of late November 2023):

  • TODAY’S CAP HIT: $84,312,500
  • PROJECTED CAP HIT: $84,113,270
  • DEADLINE CAP SPACE: $150,000
  • CONTRACTS: 45/50
  • ROSTER SIZE: 22/23


While a number of key Oilers players have no-movement-clauses, it’s only a matter of time until contract expires and these players look elsewhere to try and win a championship. Here’s a snapshot of the cap situation for the Edmonton Oilers over the next couple of seasons:

2. Peter Chiarelli – the man put the Oilers in salary cap hell (he did the same in Boston, but Boston was able to work their way out of it. Peter Chiarelli’s tenure with the Edmonton Oilers was tumultuous at worst and his regime was one that many fans suggest set the team back five years. In his nearly four years in Edmonton, he made countless head-scratching moves, such as overpaying on numerous contracts, struggled to find depth wingers and secure a starting goaltender. Names such as Brandon Manning, Ryan Spooner, and Tobias Rider ring a bell with anyone?  Didn’t think so. All players that Chiarelli brought in, and traded assets or decent players for. Did you know that the Oilers could have selected Matt Barzal in 2015?  Oh wait Chiarelli traded that pick (along with another) for Griffen Reinhart. Then how about the Taylor Hall for Adam Larsson trade? Now I actually like Larsson a lot (and he was a good Oiler), but you cannot tell me that at the time you could not have received more for Taylor Hall than getting back Adam Larsson. Pete Chiarelli was a failure in Edmonton.

Don’t take our word for it, check out:

What gets us the most is that Peter Chiarelli has a degree in finance (scratches head)… how does he mis-manage salaries so bad in the tight Cap-era?  The answer is apparently easily.  The Chiarelli regime and left a deep hole for his successor… which brings us to…

Ken Holland – not nimble enough, not looking at where the true needs are, going too much to his “Detroit ways”.  Holland has let marquee superstar Connor McDavid down, plain and simple. Lack of depth scoring, lack of shut down dee, lack of consistent goaltending… you name it, Ken Holland has not delivered for the Oilers. Many suggest, and rightfully so, that it should have been Holland who should have been let go and not Jay Woodcroft and Dave Manson. Ken Holland is paid well, and while he is in the final year of his 5-year contract with the team he virtually sat on his hands doing nothing this past summer to improve the team.  Part of the reason, see #2.

Since arriving Holland made many moves to support his two superstars and during his four seasons the Oilers amassed the 8th most points and third most regulation wins. They’ve played the 9th most playoff games and Holland has built the Oilers into a legitimate Stanley Cup contender. BUT, they still have not made a Stanley Cup finals appearance. Has Ken Holland done enough to get the Oilers to where they should be?

When the Edmonton Oilers introduced Ken Holland as their General Manager in May 2019, once of his quotes was “You’ve got to make more good decisions than bad decisions. And I think I made more good decisions in Detroit than bad decisions.” Can the same be said in Edmonton? Here’s a look at what he did in Detroit, but really at the end of the day has he accomplished what was asked of him in Edmonton? Let’s keep this team performance based. Last year the Oilers went out in the second round of the playoffs to the eventual Stanley Cup champion Vegas Golden Knights. The year prior the Oilers exited in a third round sweep at the hands of the eventual Stanley Cup champions Colorado Avalanche. Some may say that’s pretty good, but by my measure that still equates to no Stanley Cup final appearance.  Three years ago they lost to Winnipeg in the first round, the year prior they lost to Chicago in the qualifying round. The year before they missed the playoffs entirely (which is where the team is at today).  In the four years under Ken Holland the Oilers have yet to make an appearance in the Stanley Cup finals. He was brought to Edmonton to help take this team to the promise-land. He has failed to do so and a couple of good coaches have lost their jobs as a result (see: Jay Woodcroft, Dave Mason).

There have been some missed opportunities with this team. When you have the games greatest player of the past thirty years and you cannot assemble a supporting cast to win a championship, that can only be perceived as a failure. Ken Holland’s tenure as Oilers GM may be good, but it hasn’t been great in the sense that nearly five seasons at the helm and Connor McDavid has still not raised the Stanley Cup.

The Edmonton Oilers fanbase have high expectations (and why shouldn’t they?). Oilers fans want nothing more for the team to succeed and enjoy success. Right now, this team is hard to watch and everyone in Oil-Country is frustrated. Think about it from the players perspective. These guys are professionals, they don’t want to lose, they want to win. Something is not right with this team, and it appears that no one has been able to unlock what ails this team. This could very well be a long winter for the Edmonton Oilers and their fans, but you have to think that it will improve at some point. The question is will it improve enough to salvage this terrible start to the season?

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