The Edmonton Oilers' decision to let Dylan Holloway slip through their fingers last summer is quickly becoming a costly mistake. After signing a two-year, $2.2 million offer sheet with the St. Louis Blues, the former first-round pick from 2020 was left to flourish with his new team. The Oilers passed on the chance to match the deal that saw not just Holloway, but also fellow defenceman Philip Broberg, join the Blues as they continue to make substantial impacts in their respective roles.
Initially, when the Oilers opted not to match the offer sheet, Holloway had yet to fully establish himself as a permanent player in the NHL. Despite this, he had a promising performance during Edmonton's playoff run to the Stanley Cup Final the previous year, even showing flashes of chemistry alongside star player Leon Draisaitl. However, as we enter the 2025 season, it’s evident that Holloway’s career trajectory has shifted dramatically. In his first full season with the Blues, he has quickly solidified his spot in the lineup, recording an impressive 23 goals and 58 points in just 72 games. Currently, he ranks third on the team in points, trailing only Jordan Kyrou and Robert Thomas.
Furthermore, Holloway is on pace to finish the season with an eye-catching 76 points, demonstrating that he is now not merely a roster player but an impact player for the Blues. In a classic twist of irony, the Oilers are currently seeking a player with exactly his skill set after ineffective free-agent additions in Viktor Arvidsson and Jeff Skinner failed to meet expectations.
Holloway’s rise has been recent newsworthy, catching the attention of fans and analysts alike. On March 17th, 2025, he was named one of the NHL’s three stars of the week, alongside Minnesota goaltender Filip Gustavsson and Vegas center Jack Eichel. Gustavsson achieved a perfect record with a goals-against average of 0.67, while Eichel led the league with seven points. Meanwhile, Holloway's stellar performance continued to solidify his reputation, underlining how badly the Oilers have missed his talents.
Oilers General Manager Stan Bowman recently addressed the decisions made regarding Holloway during an appearance on the program 'After Hours.' He indicated that the choice to not match Holloway’s offer stemmed from salary cap constraints. “It really came down to a fundamental salary cap challenge,” Bowman stated. “We wouldn’t have the team we have now if we matched either one of those offers... We would have had to gotten rid of a pretty core player.”
While Bowman’s explanation sheds light on the challenging decisions faced by NHL teams juggling financial limits, critics have pointed out that the financial maneuvering has been questionable. A notable point raised was the Oilers’ recent move to bring in Vasily Podkolzin, whose $1 million cap hit came just before Holloway's departure. The situation seems to indicate that squeezing in Holloway’s salary of $2.2 million could have been possible without drastically altering the team’s dynamics.
As the season progresses, it is evident that the consequences of the Oilers' decisions will continue to ripple through the roster. Holloway is no longer fighting for a spot; he is firmly established as a key player for the Blues, illustrating precisely the caliber of talent the Oilers were willing to let go. At a time when the Oilers are striving for success in the postseason, Holloway's contributions to the Blues may cast an even longer shadow of regret over Edmonton's management in hindsight.
The reality is the Oilers are left searching for a player to fill the very gap that Holloway left. With the pressure mounting on the current roster to perform, the decision made a while back to let go of a promising young talent like Holloway raises questions about the forward-thinking decisions made by the Oilers’ front office.
As he continues to excel at $2.2 million, Holloway’s successful season in St. Louis will serve as a stark reminder of what once was—and potentially, what could have been—for the Edmonton Oilers. How they reconcile their financial decisions with on-ice performance will be critical in determining their fate in the coming playoff race.
