A player's new deal just made Stan Bowman and Edmonton's worst mistake permanent
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Daniel Lucente
Jun 2, 2026 (10:53)
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Photo credit: Perry Nelson-Imagn Images
Stan Bowman's offseason is falling apart on two fronts simultaneously, and Oilers fans can see the wreckage piling up in real time.
Dylan Holloway, Philip Broberg, Sam O'Reilly. That post from an Oilers X account lays it out plainly.
Edmonton still needs a top-six winger with speed and size, a puck-moving left-shot defenseman, and a third-line center.
Those are the exact profiles they let walk in the summer of 2024 when Bowman declined to match the St. Louis Blues offer sheets.
The extension that locked the door
The part that should terrify Edmonton is not the original departure. It is what happened on May 1.
The Blues signed Holloway to a five-year, $38.75 million extension with a $7.75 million cap hit running through 2031.
That deal landed one day after Anaheim eliminated the Oilers in the first round.
Holloway had 114 points and a plus-34 rating across 136 games in two seasons with St. Louis.
He erupted for 34 points in his final 25 games this season alone. This is no longer a gamble that might not work out for the Blues.
It is a locked-in top-six forward producing at near point-per-game pace on a divisional rival's roster for the next five years.
Edmonton got a third-round pick as compensation. That math gets uglier every month.
Two doors closing at once
Meanwhile, the Vegas Golden Knights continue blocking Bowman from even interviewing Bruce Cassidy, his top coaching target.
The NHLCA called the move unprecedented. Cassidy himself went on Spittin' Chiclets and said publicly he wants to work but contractually cannot walk away.
So Bowman cannot replace the players he lost and cannot hire the coach he wants. Connor McDavid's new extension kicks in this summer, and the captain called his own team "average" after the playoff exit.
The window is not just shrinking. The same front office decisions from 2024 are actively bricking it shut from both sides.
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