There is no way the oilers could match those offer sheets for the only two prospects they had but why did it come to that? Coaching? Management ? Win now mentally? Well guess what they didn’t and as I say the cupboards are bare and if they don’t win next year they are screwed when all those value contracts for veterans are up.
Not retaining Holloway and Broberg sucks for sure, especially Holloway who looked to be a top-6 callibre player as soon as next year. However, it doesn't mean the death of the Oilers future. Unlike what a lot of the writers and instagram commenters will tell you, this doesn't mean that the Oilers cup window is now 1 year and that's it. The Broberg deal would have likely been an anchor for the next few years. He could definitely blossom into a top-4 D, but a good stretch of play in the playoffs doesn't suddenly mean he's an elite d (especially considering he was riding a high shooting percentage throughout his time in the playoffs). When you consider that he's making 4+ million now, he's a luxury the Oilers can't afford.
There are still a few prospects in the system who have a pretty good chance of making the team and being impactful in the next couple years. First of which is Matt Savoie, who has top-6 potential, he needs to work a bit on his defense and physicality, but has elite offensive skills. I really like Beau Akey as well, I see him as a future 2nd unit powerplay QB behind Bouchard who is decent in his own end too. Along with Matvei Petrov, Roby Jarventie, Sam O'Reilly, Eemil Vinni and more.
It's not an elite prospect pool for sure, but its definitely not devoid of talent. It's almost impossible to maintain an elite prospect pool as a contender. Even if you aren't trading all your picks for "win now" assets, they're going to be pretty late picks.
The main reason I think it's a bit silly to think the Oilers cup window is over after this or next year, and could be another 3 to 4 years, with a another window opening in years 5-8 of Connor and Leon's new deals when the cap goes up, is that they have been able to add solid veteran help on cheap deals. Look at Skinner, Arvy and Henrique, all 3 players could have gotten more money elsewhere. Skinner is a guy with 30 goal potential next year on a 3 mil $ a year salary. These players signed these team friendly contracts because they see the Oilers as a destination where they can win a cup. This is especially the case for Skinner who has played over 1000 NHL games and hasn't set foot on playoff ice yet.
There's no reason this can't continue, if they have another deep run next year, they will finally achieve perennial contender status in the eyes of the league, making them an attractive destination for players in the latter half of their careers seeking their first cup, or to win one more before retirement.
Next season alone: Claude Giroux, Brent Burns, Brock Nelson, Taylor Hall, Kyle Palmieri, Gustav Nyquist, Evgeny Dadonov, and more all fit this mold. There are tons of this type of player available every year.
When it comes to the youth, I'm not sure we're going to see the Oilers doing much at the draft in the next few years, with very few assets available, but this management (mostly Jeff Jackson) has shown they're more than willing to get creative when it comes to acquiring prospects.
So basically: Don't panic about the Oilers prospect pool, it's not great but it's not devoid of promise either, the loss of Holloway and Broberg isn't great but also isn't really that big of a deal, no the Oilers cup window isn't just next year and then that's it.