The Oilers, and Connor McDavid, wasted another year of contention. What went wrong? What's next?

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The stakes were raised considerably when McDavid came to the organization with an offer it couldn’t refuse. Not only did he leave millions of dollars on the table last October with a contract extension that didn’t include a salary jump, but McDavid officially stamped a 2028 expiry date on the club’s contention window by deliberately selecting a two-year term for his new deal. “Two years makes a lot of sense,” McDavid said then. “It gives a chance to continue chasing down what we’ve been chasing down here with the core guys that have been here, and (leaves) a little bit of money (for the team) to work with, too.” A premium was immediately added to each remaining year in which the game’s best player was assured to wear royal blue and orange, which is why Thursday’s season-ending loss to the precocious Ducks carried added significance. Coming off consecutive trips to the Stanley Cup Final, and entering a playoffs in which McDavid said “it really feels like it’s anybody’s year,” it was definitely not their year. McDavid clearly was compromised by an ankle injury that limited his game-breaking agility against the Ducks, and he wasn’t alone. Leon Draisaitl and Zach Hyman looked to be playing through pain during the series, while defensive-minded centers Jason Dickinson and Adam Henrique were each forced to miss multiple games. However, those springtime injuries only tell a fraction of the story about what went wrong for the 2025-26 Oilers. This was a team that finished with 93 points – its lowest total since 2018-19 – and still somehow ended up with home-ice advantage for a series with the Ducks, who qualified for the playoffs with a minus-15 goal differential. Edmonton should have had the upper hand in the “pillow fight.” Instead, the Oilers squandered a lead in three of the four games they lost to Anaheim, getting soundly outplayed on special teams throughout. The main reason McDavid spent so long contemplating the $25-million, two-year extension he signed on Oct. 6 is that he had reservations about the direction of the team. His desire to win in Edmonton alongside Draisaitl, Hyman, Ryan Nugent-Hopkins, Darnell Nurse and other roster mainstays was stronger than ever, but he was mindful of the possibility of a step back — like the one that ended up occurring. “There’s no secret,” McDavid said in October, “that with a team that pushes for it every year like we have for the last number of years — four or five years we’ve given up first-round picks and prospects and all of that stuff — there’s not a ton of young guys (coming up in the organization), you know?” Plenty more futures were expended in the months that followed, with only negligible results to show for them. Management made a pledge to McDavid during a series of conversations last offseason about remaining all-in on the chase for a championship. They promised to rebalance and improve the roster around their superstar forwards. And McDavid showed faith in that plan by requesting a below-market contact that left valuable room to maneuver under the cap ceiling. “He’s curious,” Oilers general manager Stan Bowman said then. “He likes to know what’s coming and what the thoughts are and how I see the team and how we can get better. It’s all very good discussions, good dialogue back and forth. He’s a very smart guy in addition to being an amazing player. “He’s got a lot of good ideas, and that’s why it’s fun to talk hockey with him.” It’ll be interesting to hear if the tone of those conversations changes following a loss to the Ducks that no one in Edmonton saw coming. This one hurt. The Oilers fell 14 wins short of lifting the Cup after being two wins and one win shy, respectively, in the previous two years. McDavid’s burning desire to bring the Oilers to the promised land remains, despite the setback, according to league sources, but he’s likely going to expect management to deliver on specific roster adjustments this summer, rather than accepting general promises. The road to a first-round elimination, and a roster in such need of real change, was not short. When Bowman took over the general manager’s job in July 2024, he did so with a surprise on the way — and not a pleasant one. On Aug. 13, at a point in the offseason typically still reserved for rounds of golf and Caribbean vacations, the St. Louis Blues tendered offer sheets to a pair of young Oilers. Forward Dylan Holloway and defenseman Philip Broberg were former first-round picks and far from finished products — both had spent time in the AHL during the 2023-24 season — but they represented something that, under Bowman’s predecessor Ken Holland and president Jeff Jackson, the Oilers had seemed to terminally lack: quality depth with the potential for growth. St. Louis took advantage of the untenable cap situation. Jackson, acting as interim GM after Holland’s exit, on July 1 signed a raft of veteran free agents — Henrique, Viktor Arvidsson, Jeff Skinner, Connor Brown, Corey Perry, Mattias Janmark, Josh Brown and Troy Stecher — blowing past the salary cap and putting deals for RFAs such as Holloway and Broberg on the back burner. The thought, at the time, was that the Oilers would figure things out with both in due time and agree upon low-cost bridge deals. That’s not how it played out. Holloway and Broberg both signed bridge deals, but they did it with the Blues. Rather than match the offers and create a situation in which he’d have to make an unplanned trade of a high-cost player or two, Bowman let Holloway and Broberg walk, taking back second- and third-round draft picks as compensation. Bowman’s priority at the time, one he cited as part of the reason for the decision, was figuring out a new contract for Drasaitl. “(Holloway and Broberg) can probably grow into those deals, but as of today, they’re way above their actual performance,” Bowman told The Athletic’s Pierre LeBrun when the dust had settled. Both immediately emerged as important, long-term pieces in St. Louis. Since then — even through two Cup final runs — Bowman has been chasing the exact kind of medium- and short-term solutions Holloway and Broberg would’ve offered, and he’s missed on more swings than not. Vasily Podkolzin, acquired from the roster-squeezed Vancouver Canucks in August 2023 for a fourth-round pick, was an early win, and pound for pound, possibly Bowman’s biggest win. A feisty, physical middle-six winger with enough skill to score 20 goals or more, he emerged as a key contributor during the 2025 playoffs and carried it over into 2025-26. Bowman’s next trades of consequence, at the trade deadline in March 2025, had a through-line. He was adding depth players, albeit ones who’d make sense at the right price, at an immense cost in terms of outgoing assets. Trent Frederic, a solid bottom-sixer with Boston, primarily cost the second-round pick Edmonton received for the Holloway offer sheet, along with a fourth-rounder. Jake Walman, a puck-moving top-four defenseman who’d thrived after San Jose acquired him from Detroit in a contract dump, cost a conditional first-rounder. After the 2025 Cup run, both would sign long-term deals (Frederic for seven years at a $3.85 million cap hit, Walman for eight years at $7 million), locking them into Edmonton’s core, and neither has made those contracts look particularly good. Walman has become an all-defense bottom-sixer at a premium price, and Frederic was a healthy scratch against the Ducks. Meanwhile, of those eight free agents Jackson signed, only Henrique, a fourth-line center who was injured against Anaheim, and Josh Brown, who played 10 NHL games in 2025-26, remain with the organization. Bowman’s first real crack at free agency with the Oilers, meanwhile, wasn’t fruitful — he had extensions for McDavid, Bouchard, Frederic and Mattias Ekholm to worry about and, the thinking went, a goaltending problem to solve. Stuart Skinner, after three seasons worth of overall solid play, had been benched twice during the 2025 playoffs, and backup Calvin Pickard was not a long-term solution. Bowman signed Kasperi Kapanen, who’d come off the scrap heap to provide decent postseason minutes, to a one-year, $1.3 million deal and fourth-line center Curtis Lazar for one year and $775,000. Both have delivered, to some degree. The highest-profile attempts at navigating the salary cap while addressing the middle six for 2025-26, though, fell flat. Andrew Mangiapane (two years, $3.6 million) was waived after 52 games and prospect Isaac Howard, acquired from the Tampa Bay Lightning in July, couldn’t stick in the NHL. One hole up front would be plugged by Matt Savoie, a quality young winger acquired from the Buffalo Sabres for center Ryan McLeod. Savoie started the Ducks series on McDavid’s wing and did not score a goal in the series. (McLeod is centering Buffalo’s second line in the postseason.) Another opening went to Jack Roslovic, who signed on Oct. 8 for one year and $1.5 million. He scored 21 goals in the regular season and, like Savoie, none against Anaheim. The goaltending situation went unaddressed before the inconsistency Skinner battled during his first three NHL seasons began to look more like a feature than a bug. By December, Bowman was ready to move on. That decision may have been the correct one, but the timing was suboptimal and the specifics were worse. Bowman sent Skinner to the Pittsburgh Penguins for Tristan Jarry, a less-consistent, more-expensive replacement, along with a second-round pick and, bafflingly, Brett Kulak, a useful, playoff-proven defenseman. In Pittsburgh, Skinner was good enough to be the Penguins’ Game 1 starter in a first-round matchup with the Philadelphia Flyers. Kulak, meanwhile, was flipped to the Colorado Avalanche, where he’s still playing as a second-pair defenseman for the Presidents’ Trophy winners. With Edmonton, Jarry put up a .857 save percentage and saved fewer goals than expected in 13 of 19 appearances before losing his job down the stretch to journeyman Connor Ingram. Jarry is signed for two more seasons at a $5.375 million cap hit — a fact that compounds the issue of his poor performance. In March, before Ingram took control of the job, Edmonton seemingly scrambled to fortify the roster with Dickinson and defenseman Connor Murphy. Those two were acquired in separate trades with the Chicago Blackhawks and cost the Oilers first- and second-round picks, partially because their cap situation necessitated 50 percent salary retention by Chicago. Both are good players. Neither were the scoring forward Edmonton hoped to add at the deadline, and Murphy was a de facto replacement for Kulak, who was sent to Pittsburgh in part to create space for Jarry’s contract. In the series against Anaheim, Dickinson struggled to stay in the lineup due to an ankle injury. Murphy was part of an ineffective penalty kill and a defensive pairing that was outscored in its minutes, and Jarry saved 34 of 38 shots in one game’s worth of relief of Ingram — a 4-3 overtime loss. When he went back to Ingram for Game 5, coach Kris Knoblauch complimented Jarry, but called Ingram “our guy.” “And now that our season’s on the line,” Knoblauch continued, “we felt that we would go with our guy.” It was Ingram in net for Game 6, too. He allowed four goals on 26 shots. Patience is not a virtue typically associated with Oilers owner Darryl Katz. The added urgency brought on by a closing Cup window could also influence whether any significant organizational changes follow a season that fell way below expectations, with Jackson, Bowman and Knoblauch all under scrutiny. From a roster perspective, Edmonton needs to solve a problem as old as McDavid’s NHL career: Who is starting in goal? Jarry has two pricey years remaining on his contract, but did not imbue any confidence that he can capably shoulder a meaningful load. It wouldn’t be surprising if Edmonton looked to move on. Ingram is a pending unrestricted free agent, and the list of other potential July 1 goaltending options carries nothing resembling a sure thing, It includes Skinner, Frederik Andersen, Vitek Vanecek, David Rittich and 37-year-old Sergei Bobrovsky. Perhaps there’s a trade to be explored with the St. Louis Blues for Jordan Binnington. The Vegas Golden Knights have a well-paid backup in Adin Hill, but it’s hard to imagine them rushing to help out a Pacific Division rival. It’s going to be tough. It’s going to be talked about. Up front, there’s also work to be done, with Dickinson, Henrique, Roslovic, Kapanen and Lazar all eligible to test the open market. If the price is right, each has a case to return. But in a rising cap environment, there could be the allure of bigger paydays elsewhere to contend with. Murphy is the only pending UFA among the defensemen, but the biggest decision arguably surrounds Nurse. He owns a no-movement clause on a contract with $9.25 million owed in each of the next four years. If the Oilers could clear that cap commitment, it would free up money for other needs. They need to try. However, as the Oilers entered the offseason sooner than expected, the biggest source of optimism could be found in the long summer that comes with it. They’ll get additional rest. Because unless something unexpected happens, it’s going to be up to the same old faces to make sure one of their two remaining shots at a championship doesn’t get wasted next year. Spot the pattern. Connect the terms Find the hidden link between sports terms