The Edmonton Oilers struck gold, winning the 2015 NHL Draft Lottery and the right to select Connor McDavid first overall. This is what the organization needed in hopes of ending the decade of darkness and once again becoming a respected and competitive team. The organization ended its playoff drought in 2017, advancing to the second round before missing the next two seasons. But the Oilers have made the playoffs every season following the pandemic, including back-to-back Stanley Cup Final appearances and three trips to the Western Conference Final in the past four seasons.
Edmonton found some success, but still has nothing to show for it. It took until years nine and 10 of the McDavid era to finally appear in the Cup Final. The Oilers’ captain is 28 years old, turning 29 in January, and the clock is ticking. Those early years were wasted, and the team should’ve been more competitive back then. They weren’t, and management is the main reason why. The organization failed to build a good team around him. With that said, here are five reasons why the Oilers haven’t won the Stanley Cup in the McDavid era.
Poor Drafting, Developing & Draft Day Decisions
The Oilers have been notoriously poor at drafting and developing talent before and after McDavid entered the league. While the Oilers have made decent first-round selections, they’ve struggled to find NHL-quality players in the later rounds. Between 2016–2020, they drafted Jesse Puljujarvi, Kailer Yamamoto, Evan Bouchard, Philip Broberg, and Dylan Holloway in the first round. The Oilers developed these players, but unfortunately, only one of them is still on the team. That demonstrates just how bad their player development is and their inability to trust their younger talent.
Related: Edmonton Oilers’ Missed Draft Opportunities
Since 2016, Ryan McLeod has been the only non-first-round pick to play meaningful minutes for the organization, and he is no longer with the team. The only other second-round pick to suit up was Raphael Lavoie, but he didn’t pan out. They’ve also made some first-round blunders, most notably in 2021. They traded the 20th overall pick to the Minnesota Wild and moved down two spots to select Xavier Bourgault, 22nd overall. Edmonton desperately needed goaltending, and they had a quality goalie prospect available at 20th overall in Jesper Wallstedt, but passed on that opportunity. To make matters worse, they missed on their selection because Bourgault was a bust, and Wyatt Johnston, who’s turning into an elite player, went next. The Oilers haven’t drafted well, which has long-term negative effects.
One of the Oilers’ worst decisions came on draft day, but it wasn’t a selection; it was a trade. Then-general manager Peter Chiarelli acquired Griffin Reinhart from the New York Islanders in exchange for the 16th and 33rd overall selections in the 2015 Draft. The Islanders selected Mat Barzal with the 16th pick, and Reinhart only played 26 regular-season games with the Oilers, recording one assist. Meanwhile, Barzal has turned into a great player, recording 462 points in 530 games. Imagine how he would’ve performed with Edmonton alongside McDavid for the last decade. Yes, the Oilers were desperate for defencemen, but this was a panic move, and it will go down as one of their worst trades in the salary cap era. If they made better decisions on draft day, maybe they would have a few Cups to show for it.
Losing Broberg & Holloway
Another management blunder was not re-signing Holloway and Broberg during the 2023-24 season. As a result, they lost them both to offer sheets last August. This is another example of how the organization continues to mismanage its prospects and poorly manage its assets. The Oilers claim they want to get younger, but they had two young players right in front of them and didn’t value them. Instead, they decided to sign veteran forwards Jeff Skinner and Viktor Arvidsson last offseason rather than sign their young, homegrown talent. They got older and slower, and didn’t replace that speed. The two players they signed had a similar combined cap hit to Broberg and Holloway, so why not prioritize them instead? Broberg and Holloway would’ve likely had a bigger impact in the playoffs than Skinner and Arvidsson, since those veterans were constantly healthy-scratched. This was another terrible managerial decision that they are trying to overcome.
Oilers Hired Ken Holland Over Bill Zito
This is another example of what could’ve been. Once Chiarelli was relieved of his duties, the Oilers hired Ken Holland as their new general manager in 2019. However, they also interviewed Bill Zito for that position, but went with the more experienced Holland instead. Zito went on to win back-to-back Stanley Cups with the Florida Panthers, making some great deals along the way. He acquired Matthew Tkachuk, Sam Bennett, and Brad Marchand, shaping the Panthers into perennial Stanley Cup contenders. Meanwhile, the Oilers are still looking to get over that hump. If only Edmonton had hired Zito instead of Holland, things would’ve been different in Oil Country, and maybe McDavid would have multiple rings.
Darnell Nurse & Jack Campbell Contracts
The most egregious managerial decisions were signing Darnell Nurse and Jack Campbell to lucrative contracts. After signing two separate bridge deals, Nurse got a massive eight-year contract, with a hefty $9.25 million cap hit, including a full no-movement clause (NMC) until 2027. That deal doesn’t expire until the end of the 2029-30 season, which hinders the organization’s ability to improve other parts of the roster. They are constantly strapped against the salary cap and don’t have the funds to upgrade other positions, like goaltending. While Nurse is a solid NHL defenceman, he’s not elite, but is being paid like one.
Edmonton also inked Campbell to a five-year deal, with a $5 million cap hit in 2022. The Oilers desperately needed a number-one goaltender, but the Campbell experiment failed miserably, leading to his buyout in 2024. He had a brutal 3.53 goals-against average (GAA) and an .886 save percentage (SV%) in 41 games with Edmonton. He was flat-out bad, and now, the Oilers have more dead money on the books until 2030. While the 2022 free agent goaltender class was weak, Marc-Andre Fleury and Darcy Kuemper were other options available. It’s tough to tell how someone would fare on a new team, but it was still a bad contract. Cap space is just as valuable as prospects in your system, and right now, the Oilers have neither.
Goaltending
This one’s the most obvious, but goaltending has been the Oilers’ biggest problem for decades. Timing is everything, and when the Oilers were coming out of the decade of darkness, Cam Talbot was the netminder. Talbot played four seasons in Edmonton, and he was great for the first three, leading them back to the playoffs in 2017. He had a .917 SV% in 2016-17, a .919 SV% in 2016-17, and a .908 SV% in 2017-18. He had a sparkling .924 SV% in 13 games during the 2017 Playoffs, but unfortunately, the team was not yet ready to compete for the Stanley Cup. The fan base prays for numbers like those now with Stuart Skinner, but isn’t getting them. As a result, they’ve come up just short. While their recent Cup Final losses aren’t solely due to goaltending, it’s by far their weakest position, and it hasn’t been adequately addressed.
The common denominator in all of this is management. It’s not just with the general managers, but it goes beyond that. Owner Daryl Katz and former Chief Executive Officer Bob Nicholson share some blame in this as well. Nicholson was responsible for hiring Chiarelli and Holland, which set the organization back. The Oilers didn’t have the right people in place. Once they got McDavid, they needed to field a quality team around him, and failed to do so for the longest time. They are finally starting to find success, and hopefully, they will win that ultimate prize, but it should’ve happened sooner.
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