The hockey world is focused on Edmonton and what will happen between the Oilers and Connor McDavid; however, several factors have brought the two parties to this point, with the biggest one being the offer sheets to Dylan Holloway and Philip Broberg.
We all remember that on August 13th, 2024, the St. Louis Blues sent two offer sheets, one to Holloway and one to Broberg. Both were signed and accepted by the players. New Oilers General Manager Stan Bowman needed to decide within seven days whether to match the offer sheets or receive the proper compensation from the Blues and General Manager Doug Armstrong.
Can the Edmonton Oilers Survive Losing Both Dylan Holloway and Philip Broberg?
We know how the scenario played out, and the Oilers did not match the offer sheets, losing two key young players who were essential pieces in their first trip to the Stanley Cup Final in 2024. However, looking into even further, Bowman was thrown into a scenario that he should have never been in by the CEO of Hockey Operations, Jeff Jackson.
Jackson let former GM Ken Holland go before the start of Free Agency in 2024, and Jackson handled that free agency period, prioritizing signing veteran players over the young guys in the system. This rubbed Dylan Holloway the wrong way as he told Andy Strickland and Cam Janssen on the Cam and Strick Podcast earlier in the week.
“It rubbed me the wrong way how little Edmonton thought of me in our contract negotiations. I’m an Alberta boy, I wanted to go back to a team we went so far with, but as soon as Edmonton didn’t reciprocate that feeling, I was all in on St. Louis,” Holloway said.
Not surprised to see these comments from Holloway.
The organization needed to make a decision on him and Broberg long before those offer sheets came. Too much up & down
And these guys needed to be the 1st order of business but again not having a GM in place last July 1 has… https://t.co/HIX9CcOfZa
— Jim Biringer (@JimBiringer) September 2, 2025
Edmonton Oilers Had a Top Four Defenseman in Philip Broberg
And Holloway has every right to feel this way. Edmonton mishandled Broberg and Holloway throughout their development inside the organization. Whether it was Jackson himself, Holland, or members of the staff, there never seemed to be a belief in Holloway or Broberg or else those guys would have been given contracts on or before July 1, 2024.
This started by not having a GM in place on July 1. Jeff Jackson mad the calls and instead of taking care of Broberg & Holloway the Oilers got slower.
I mentioned this to @stevekouleas when he talked about the Oilers a few ago on @SiriusXMNHL. Needed a GM in place.… https://t.co/KSFrTxKyKG
— Jim Biringer (@JimBiringer) April 24, 2025
As NHLRumors.com documented last year when these offer sheets happened, the Oilers should have matched these contracts. While Leon Draisaitl was a priority and the money might not have been there, Edmonton lost two key depth pieces on its roster that would have played crucial roles this season.
Remember, over the course of last season, Broberg and Holloway were frequently called up and down from the AHL, and there was never a clear development plan in place for either player. Nothing was presented to either player. You saw what both players did in the 2024 Stanley Cup Playoffs, especially Broberg, who stepped up in the Stanley Cup Final and played strongly defensively.
That strong play carried over to the Blues this season. Holloway set career highs with 63 points (26 goals and 37 assists) in 77 games playing top-six minutes for the Blues under head coach Jim Montgomery. Meanwhile, Broberg, before his injury, was proving why the Oilers needed to keep him the way he slotted into the Blues’ top four so seamlessly. Broberg finished the season averaging around 16 minutes of ice time, recording career highs with 29 points (eight goals and 21 assists) in 68 games.
What the Edmonton Oilers Offered Philip Broberg and Their Need for Better Development Paths
Again, Jeff Jackson put current Oilers GM Stan Bowman in a tough spot for not having a GM in place on July 1st, 2024. Still, the mishandling of these players by Edmonton left a bad taste in their mouths as they looked for the opportunities they felt they deserved elsewhere.
Just imagine if Broberg and Holloway were still on the team; maybe this Connor McDavid extension wouldn’t be taking as long, because he knows what this team is capable of down the road.
Have you subscribed to our YouTube channel? Rumor roundups and hot topics from around the league. We’re also posting some stuff on Instagram.
