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Charlie McAvoy, Boston Bruins (Amy Irvin / The Hockey Writers)

Edmonton Oilers’ Missed Draft Opportunities

Originally posted on The Hockey Writers | By The Old Prof | Last updated Aug 13, 2025 2:25 PM ET

The Edmonton Oilers boast a once-in-a-generation duo in Connor McDavid and Leon Draisaitl. But in today’s NHL, championships aren’t won on the backs of two players alone. You need a strong supporting cast, and the most cost-effective way to acquire it is through the draft.

From 2012 to 2017, Edmonton made first-round picks that failed to address glaring roster holes — particularly on defense and in net. Even more frustrating, the players they passed on weren’t hidden gems from the sixth round; they were obvious, high-profile talents taken shortly after Edmonton’s pick.

Here’s the year-by-year breakdown of what could have been for a team that has come so close but failed to take home the Stanley Cup. Oh, what might have been.

The 2012 Entry Draft: The Oilers Missed Two Solid Defensemen

Looking back at the 2012 NHL Draft, it’s hard not to imagine how different things could have been for Edmonton if they’d chosen one of several standout players still on the board. Morgan Rielly, taken fifth overall by the Toronto Maple Leafs, has become the leader in games played (867) from his draft class and serves as the quarterback of Toronto’s power play. He’s the kind of two-way defender Edmonton has long needed—mobile, poised under pressure, and capable of logging heavy minutes in every situation. Over his career, Rielly has consistently driven offence, earning a reputation as one of the league’s most reliable top-pair blueliners.

Also available to the Oilers was the Anaheim Ducks’ first pick. That was Hampus Lindholm, a big, reliable defenseman who could have been the anchor that Edmonton’s top four desperately needed. Lindholm turned out to be a smart, puck-moving, gap-control blueliner who has been able to shut down opposing forwards. He’s been a stabilizing presence wherever he’s played. Since joining the Boston Bruins, he’s paired that defensive reliability with timely offence, becoming a key part of one of the league’s stingiest blue lines.

Instead, Edmonton used the first overall pick on Nail Yakupov, who was a speedy winger expected to add offensive firepower alongside Taylor Hall, Jordan Eberle, and Ryan Nugent-Hopkins. While he was less than advertised, the bigger issue was that scoring wasn’t the Oilers’ biggest problem. They needed players who could prevent goals. By grabbing one more offensive forward and ignoring their more significant defensive issues, the Oilers missed a crucial chance to address the weakness that was holding them back.

The 2016 Entry Draft: The Oilers Let Two Elite Defensemen Slip Away

In the 2016 NHL Entry Draft, the Montreal Canadiens took Mikhail Sergachev ninth overall, and he later found a home with the Tampa Bay Lightning. Sergachev has grown into a mobile, physical defenseman who can log big minutes, quarterback the power play, and handle top-pair matchups with ease. He’s been a key piece on two Stanley Cup-winning teams, blending offensive skill with solid defensive play.

Charlie McAvoy was also available, and the Bruins chose him 14th overall. McAvoy turned into Boston’s defensive heart and soul. He regularly eats up 25-plus minutes of ice time, and he’s solid all over the ice. He brings size, good skating, and, best of all, a high hockey IQ. Game after game, he shuts down the NHL’s best forwards and gives his team solid play on both special teams. In short, he’s one of the NHL’s top defenders.

Instead, Edmonton used the fourth overall pick in 2016 on Jesse Puljujärvi, a skilled winger who had fallen slightly from his projected third slot. While tempting, the choice came despite the team already having a surplus of offensive talent, while the defensive corps remained thin and unsteady. Just a few picks later, teams selected Sergachev and McAvoy, who both developed into top-pairing defensemen and foundational pieces for their franchises.

By prioritizing the perceived best player available over the team’s pressing needs, the Oilers missed a crucial opportunity to build the kind of defence that wins championships. Oh, by the way, even if they had stuck with a forward in that draft, the Oilers missed a huge measure of grit and leadership up front by not taking Matthew Tkachuk. As fans of the Battle of Alberta know too well, he was chosen sixth overall by the Calgary Flames. He turned into a relentless agitator and clutch scorer, now leading the Florida Panthers’ Stanley Cup chase.

The 2017 Entry Draft: The Oilers Missed the Franchise Goalie They Needed

Perhaps the Oilers’ biggest gaffe can be found in the 2017 NHL Entry Draft, when the Oilers missed out on a potential franchise-altering goalie. Good on the Dallas Stars for selecting Jake Oettinger 26th overall. He would have become exactly what Edmonton has lacked for years: a calm, athletic goaltender capable of stealing playoff games.

Oettinger has everything you want in a modern goalie: size, lightning-quick reflexes, and a calmness that lets him make big saves without ever seeming flustered. Even better for the Stars, he shines during the playoffs. His positioning, rebound control, and ability to read plays make him a game-changer. He’s the kind of last line of defence that can steal games for his team.

Fans can only wonder what might have been if Edmonton had gone after Oettinger. Would they bet two-time Stanley Cup champions by now? Who knows, but it would have shifted their drafting strategy and finally addressed one of their most glaring defects.

Instead, the Oilers used their first-round pick on Kailer Yamamoto, a speedy, flashy winger who showed potential but battled injuries and inconsistency. While he brought energy, the team’s bigger need was clearly in the crease. Targeting a goalie like Oettinger might have saved Edmonton from taking risky swings on netminders like Jack Campbell and could have changed the story of several playoff exits.

Speaking of the Stars, they got lucky a second time when they selected Jason Robertson with the 39th overall pick in the second round. Robertson turned into a 40-goal winger with a high hockey IQ. He’s capable of controlling the pace of the game, reading defenders, and creating scoring chances out of nowhere. He combines skill, vision, and size and has become an offensive talent. Even if Edmonton had missed Oettinger, grabbing Robertson would have helped the team pick up the secondary scoring it needed to complement McDavid and Draisaitl, thereby carrying the team through the playoffs.

The Oilers Followed a Pattern That’s Hard to Ignore

From 2012 to 2017, a clear pattern emerges: the Oilers consistently drafted players who added skill where they were already stocked, rather than addressing critical structural holes. They overlooked defence and goaltending, despite years of evidence showing those were the team’s biggest barriers to contention. At the same time, they passed on NHL-ready talent that other general managers were quick to grab. These weren’t obscure misses — they were near-misses on players who have since won Cups, anchored elite rosters, and carried teams deep into the playoffs.

The cost of these decisions has been steep. Their choices forced Edmonton to overpay in free agency and make high-risk trades to patch holes that could have been filled internally. Some of these choices have been solid; there’s no doubt. The team has benefited from grabbing Mattias Ekholm from the Nashville Predators and Zach Hyman from the Maple Leafs. (Who knew?)

Zach Hyman, Edmonton Oilers (Mandatory Credit: Kirby Lee-Imagn Images)

Still, the Oilers also strained their salary cap flexibility and limited long-term roster stability. Meanwhile, teams like the Stars, Lightning and Bruins reaped the rewards of building their own cores, giving them a regular path to contention — a path Edmonton might have followed if past drafting mistakes had been avoided.

Why These Mistakes Still Matter to the Oilers Today

While McDavid and Draisaitl are in their prime, the championship window won’t stay open forever. In a hard-cap NHL, hitting on draft picks — especially in the first round — isn’t optional. It’s the foundation of a sustainable contender.

The Oilers’ history from 2012–2017 shows what happens when you draft for flash instead of fit: you end up watching players you could have had lift the Cup somewhere else. If Edmonton wants to avoid another decade of “what ifs,” the next draft can’t be about who falls into their lap. It has to be about who fills the biggest hole in the lineup — even if that pick isn’t the sexiest name on the board.

[Note: I’d like to thank Brent Bradford (PhD) for his help co-authoring this post. His profile can be found at www.linkedin.com/in/brent-bradford-phd-3a10022a9]