Management made the edmonton oilers roster worse not better

The costly timeline of front office instability

The problems began during the 2023-24 season when the organization chose not to extend then-general manager Ken Holland. This left him in a lame-duck role, creating uncertainty that rippled through the league. Every team knew the schedule: the Stanley Cup Final could end as late as June 24, 2024, followed by the draft and free agency on July 1.

Without a permanent general manager in place by the start of free agency, Jeff Jackson was forced to handle the market himself. That decision proved costly. If the plan had always been to wait for Stan Bowman’s reinstatement, the delay only compounded the mistakes. The result was a rushed approach that prioritized short-term signings over long-term stability.

Mishandling key young talent in 2024

The first major misstep came with offer sheets from the St. Louis Blues for Philip Broberg and Dylan Holloway. These were homegrown players who had contributed meaningfully during the Oilers’ run to the 2024 Stanley Cup Final. Broberg in particular had logged heavy minutes on the blue line and played reliable defense.

Instead of matching the offers or finding creative ways to retain them, Bowman chose to let both players walk in exchange for assets. The team then pivoted to signing Viktor Arvidsson and Jeff Skinner. That choice stripped away the depth that had helped the club reach the final the year before. Good management evaluates and protects its own developing talent first.

• Broberg and Holloway were effective playoff contributors in 2024
• Arvidsson and Skinner joined a roster already lacking balance
• Cody Ceci, Vincent Desharnais, Warren Foegele, Derek Ryan, and Ryan McLeod also departed around the same time

Depth erosion during the 2024-25 season

The 2024-25 campaign brought mixed results. Most of the core returned, including Corey Perry, Evander Kane, and John Klingberg. Goaltenders Stuart Skinner and Calvin Pickard kept the team competitive enough to reach the Stanley Cup Final again. Yet the series against the Florida Panthers exposed the lack of depth that had been present in prior years.

Despite the loss, the roster still showed promise. Bowman’s first full offseason as general manager should have focused on adding complementary pieces. Instead, the focus shifted to contract negotiations for McDavid and Draisaitl, which distracted from building around the existing core.

Aggressive 2025-26 trades that backfired

McDavid’s two-year extension placed additional pressure on the front office. To create cap space, Bowman traded Viktor Arvidsson to Boston, allowed Connor Brown to sign in New Jersey, moved Evander Kane to Vancouver, and watched Corey Perry depart for Los Angeles. These moves further thinned an already shallow roster.

The goaltending experiment proved especially damaging. Despite public statements about upgrading the position, the team traded Stuart Skinner and Brett Kulak to Pittsburgh for Tristan Jarry and his full cap hit. Kulak later helped the Colorado Avalanche reach the Western Conference Final. Additional trades for Connor Murphy, Colton Dach, and Jason Dickinson cost the Oilers a 2027 first-round pick, a 2027 third-round pick, a 2028 second-round pick, and a 2029 second-round pick.

The coaching change and what comes next

Head coach Kris Knoblauch was let go before his contract extension even began after leaks surfaced about Bowman seeking a replacement. Bowman has since taken public ownership of the situation, but both he and Jackson now face immense scrutiny heading into the summer.

The upcoming offseason represents the most important period in franchise history. McDavid’s short-term deal means the team must show clear signs of progress or risk losing its generational talent. Similar challenges face other clubs like Toronto, but the Oilers’ recent decisions have only increased the distance to the Stanley Cup.

For more on the roster shakeups ahead, see this look at edmonton oilers face sweeping changes in 2026 offseason. Additional context on building around the stars is available here.

The path forward requires decisive action to restore depth and competitiveness. Without it, the window of contention could close quickly.