In Hindsight: The Chaos That Lost the Oilers 2 First‑Round Talents

With Darren Ferris (Philip Broberg’s Agent) coming out a few days ago and discussing his strategy for masterminding the dual offer sheets levied against the Edmonton Oilers, I want to look back at why the Oilers didn’t match these offer sheets, and what might have changed had they done so. The Oilers allowed two young high-draft assets to walk away, for compensation that likely didn’t match their value. Of course, values change over time, based both on how productive players are and their salaries relative to the changing cap.

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The Oilers had just come off a memorable run to the 2024 Stanley Cup Final, ultimately losing in seven games to the Florida Panthers after battling back from a 3–0 series deficit. In the offseason, Ken Holland was not brought back, and Jeff Jackson stepped in to lead the front office while the team searched for a new general manager.

Jeff Jackson Made Some Interesting Choices

Heading into free agency, Jackson made a few interesting decisions. He quickly signed Viktor Arvidsson and Jeff Skinner, while also re-signing Calvin Pickard, Connor Brown, Mattias Janmark, Troy Stecher, and Corey Perry. He then traded Ryan McLeod to the Buffalo Sabres in exchange for Matt Savoie.

With so many moves completed early, Jackson pushed his restricted free agents to the back of the priority list. He viewed those deals as easier to finalize later, choosing instead to focus first on addressing the team’s more immediate needs.

Looking further back, Ken Holland was instructed by upper management in January 2024 to prioritize signing Philip Broberg and Dylan Holloway. Whether he didn’t give those negotiations enough attention or simply didn’t push discussions far enough remains unclear. There were also reports that the Oilers lowballed both players, which may have led them to delay signing until after the season.

Broberg had already requested a trade earlier in the year, feeling he wasn’t getting adequate ice time. Holland’s continued additions of left-shot defensemen only complicated matters further, effectively blocking the young Swede’s path to securing a full-time role in the NHL.

Philip Broberg

Thanks in part to numerous injuries, Broberg played just 12 games in 2023–24 after appearing in 46 and 23 games in the previous two seasons. However, he did see action in 10 playoff games, recording three points and a +8 rating.

A young, lanky, smooth-skating defenseman, Broberg had his struggles but also showed flashes of high-end potential. He put up strong numbers in the AHL with the Bakersfield Condors and appeared justified in his belief that he was ready for a full-time NHL role.

With his trade request on the table, the Oilers were put in a difficult position and ultimately may have felt it was best to move on.

Dylan Holloway

Holloway played 36 games in the 2023–24 season, recording nine points. The previous year, he appeared in 51 games and also finished with nine points. However, he showed signs of progress during the 2024 playoffs, playing all 25 games and contributing seven points.

He flashed real potential alongside Leon Draisaitl, forming a line that offered a glimpse of what he could become at the NHL level. Since being selected 14th overall, Holloway has dealt with multiple injuries that have slowed his development. Most notably, he has battled wrist issues stemming from an injury in 2021 that required surgery, something that has continued to impact his progression at times. Holloway said:

”Yeah, my wrist is kind of mangled to be honest. It’s not ideal, but like, for hockey it’s fine. It’s just like, I can’t do push ups, I can’t bend it back. That’s a problem. I don’t know if you’ve seen, but I’ve got this massive scar. It’s nothing that’s going to hold me back hockey wise, but it’s kind of on day to day stuff, there’s stuff I can’t do with it.”

These risk factors, injury-wise, and the overall low point totals didn’t scream top-6 forward, and the Oilers ultimately risked letting him walk.

The Offer Sheets

Darren Ferris was smart in waiting until after the buyout period, so that the Oilers were kind of trapped. Then-St. Louis Blues GM Doug Armstrong smelt blood and worked in tandem with Ferris to come after the Oilers. The Oilers had made all of their free agent decisions, re-signed key forwards, and tied up most of their money. This, in the end, was a very poor decision.

Ferris took Broberg and then helped guide Holloway’s agent into making the two offer sheets at a time when Edmonton also had just brought in a new GM and had lost track of where they were in terms of their salary cap and potential to get two important deals done. Holloway’s money jumping to $2.29 million AAV was a large jump for a player with a career-high nine points. No one could have predicted the step he took the following season, which is why it’s understandable that the Oilers were hoping to keep him around for another year at around $1-1.2 million AAV. The offer sheet was an overpay based on potential. In tandem with the Broberg offer, it complicated matters for Edmonton.

Looking back, you can see why the Oilers didn’t match. Broberg had a pending trade request that didn’t seem likely to be rescinded. An injury-plagued Holloway had a career-high nine points. Holland let things drag out. Jackson got carried away because players were willing to join the Oilers. The new GM didn’t know the players well. A lot of mistakes built up into the decision to not match the offer sheets. Ultimately, the Oilers lost an 8th overall defenceman and a 14th overall forward and got back a 2nd round pick, two 3rd round picks, and prospect Paul Fischer.

What If?

What if the Oilers had matched the offer sheets? A combined $6.87 million AAV would have been tough to fit in, but the Oilers could have definitely made it work, especially if they had done the deals earlier.

However, it was not all bad. If the Oilers had kept Broberg and Holloway, Bowman likely wouldn’t have traded for fan-favorite Vasily Podkolzin. His deal is among the most team-friendly in the organization. He put up 17 even-strength goals this past season. The Oilers also likely don’t bring in Ty Emberson, who has been a solid fit and appears ready to take another step.

However, with Broberg in the fold, the Kulak and Walman trades likely don’t happen. And, with Holloway on board, Trent Frederic likely isn’t traded for and signed. Both Walman and Frederic were on Dom Luszczyszyn’s top 10 worst contract lists, which is arguable.

The Oilers would have had a much younger youth core, would have saved multiple assets in big trades, but would likely also be without a top young player in Podkolzin. Would keeping Broberg and Holloway, along with getting different assets from Walman and Frederic, have pushed them over the top in 2025? I think it might have. Holloway thinks it might have also, as he promptly fired his agent less than a year after signing the offer sheet.

Next: In Hindsight: The Quiet Trade Costing the Oilers a Top Defender