What offseason options will Stan Bowman and the Oilers explore after two championship misses against Florida?
By Jason Fink | May 1, 2026 | @THEJASONFINK on X
After two consecutive losses in the Stanley Cup Final, the Edmonton Oilers find themselves at a crossroads. That’s because they were bounced in the first round of the playoffs by the Anaheim Ducks in six games. It marks the first time since the 2020–21 season that the Oilers failed to advance past the opening round, when they were swept by the Winnipeg Jets.
Once again, shaky goaltending and defensive breakdowns proved to be the Oilers’ undoing. Even with two of the best players in the world in Connor McDavid and Leon Draisaitl, the burden they have carried over the past two seasons finally showed signs of cracking. McDavid had a relatively quiet series with just one goal and six points, while Draisaitl led the team with ten points after returning from a mid-March injury.
Now the question for general manager Stan Bowman is simple: what’s next?
A team that looked poised to get over the hump and capture its first Stanley Cup since 1990 is suddenly staring at a potential turning point. Draisaitl is 30, and McDavid just turned 29 in January. They are far from being past their primes, but the window to win with them is not endless. It narrows further if the right roster moves are not made. The Oilers already put themselves in a difficult position two years ago when they failed to match offer sheets for Dylan Holloway and Philip Broberg, allowing both to join the St. Louis Blues.
Having two superstars in their prime at the same time is nothing new for this franchise. Former owner Peter Pocklington famously traded Wayne Gretzky to the Los Angeles Kings for Jimmy Carson, Martin Gelinas, three first-round picks, and $15 million in cash. Three years later, Mark Messier was dealt to the New York Rangers for Bernie Nicholls, Steven Rice, and Louie DeBrusk. Gretzky later led the Kings to the Stanley Cup Final in 1993, while Messier captained the Rangers to a championship in 1994.
So, should Bowman consider taking a similar path and trade both of his franchise centers?
If a 32-year-old defenseman like Colton Parayko can fetch a first-round pick and a former first-round defenseman in Radim Mrtka, what would the return look like for McDavid and Draisaitl? According to hockey analyst Scott Wheeler, the Oilers rank 30th in the league in prospect depth. Their pipeline is thin. Moving one, or even both, stars could restock the system while also bringing in NHL-ready talent to stabilize the roster.
But that is only one path.
The Oilers also have glaring needs on defense and in net, where they ranked 25th in goals allowed and 20th on the penalty kill. With roughly $16 million in cap space this offseason, thanks in part to McDavid’s team-friendly extension signed last October, Edmonton has the flexibility to try to retool rather than rebuild.
Do they push their chips in one more time?
A call to St. Louis could make sense, especially to gauge the availability of goaltender Jordan Binnington. While his numbers have dipped and he lost the starting role to Joel Hofer, Binnington has proven he can deliver when it matters most. He is a Stanley Cup champion with a track record of rising to the occasion on big stages, including international play.
Ultimately, Bowman’s decision will define the next era of Oilers hockey. Whether it is a bold teardown or one last push with the game’s two brightest stars, standing still is no longer an option.
Jason Fink is a writer, husband, and dad of two based in St. Louis. A sports fan for over 40 years with a tremendous love for the St. Louis Blues and St. Louis Cardinals, he writes with the perspective of someone who’s lived every high and low. His work blends insight, storytelling, and the kind of opinions every fan has—but doesn’t always say out loud.