I think you know that I am not the conspiracy theory type. But reading between the lines, and even some of the actual lines, it sounds like Broberg's plan was not a decent contract for his current value but to get out of Dodge by hook or by crook. It sure looks like he was not happy with his prospects as an Oiler. BY playing it the way his camp did I think that is a big sign that he was not on board with the program of having him play the second pairing RHD slot.
Now if there was a "mistake" here it was in not getting something done with Holloway earlier. But even then it may not have been nearly as easy as it may seem. It sure looks like the Broberg OS plan was to get Holloway involved early as a pawn to force the Oilers into letting Broberg walk. Even listening to Holloway it sure sounds like he did not expect to end up a Blue. My guess is that if he could go back he would have probably not taken this route.
The Oilers have over the last few years really botched their cap management. Neither of the last two Gm's were at all creative in handling the cap. Most of this is on Holland but Chia still bears some blame. He was very reactive and not at all creative. A series of his moves also triggered moves by Holland , who may have been even less creative, that had cap implications even today. That left the Oilers vulnerable to a move like this. But pretty much every top contender has been in a similar position and has acted in a much similar manner without the result of an OS. Is it that St. Louis was set on breaking the norm, or was this a perfect opportunity since the player actually wanted out. Frankly, I now believe it was a combination of the two.
As to the Brown signing, as a hockey move that is still up in the air. But that contract can be fully buried so I don't think it had any significant impact on signing a guy like Holloway.
I do think Broberg was intent on leaving no matter what and Ferris had a hand in orchestrating the whole scheme, I wouldn’t even be surprised if he was in Holloway’s reps ear to convince them to sign an offer sheet to further handcuff the Oilers and increase the chances the offer to his client wouldn’t be matched. It looks like Holloway might of received bad council and it kind of seems like he knows it, I’m guessing that a lot of what he was being told was that the Oilers were highly unlikely to let him walk for only a 3rd so he could have his cake and eat it too, getting paid 2x and staying with the Oilers. But as we’ve seen time and again going for the money too early can actually hurt a young question mark player in the long run. Now he finds himself in a system he could easily get lost in on a team that isn’t as attached to his development. Very real chance he ends up like so many players before him starting at the bottom of the ladder in two years searching for a job.
Like you, I agree that the mistake Oilers management made was not doing more to get Holloway under contract but when I look at the timeline and available information here is my take on the situation.
The players sides didn’t want to negotiate new deals in season when both players were still floundering, the team was likely ok with waiting until they knew where the cap was going to end up so negotiations get kicked until after the season is over and with the cup run basically butting right up against the draft/free agency time was short but by that time Armstrong had basically signalled he was going to offer sheet players and the wheels on Ferris plan were already in motion. This is where I think Oilers management made a mistake but I feel like they believed they could handle a Broberg offer sheet in that range and they likely thought Holloway wouldn’t be foolish enough to sign one let alone be a party to signing with the same team, on the same day, 6 weeks after they were free to. The big mistake I see being made my Oilers management is that at some point in the few days before July 1 it probably would of become apparent that both players were going to hold out until free agency and they should of started putting the puzzle pieces together and maybe they did and that’s why they spent how they did on day one of free agency because maybe they felt if they were going to get backed into a corner over paying some question marks then they’d rather allocate cap to established players and not miss out on adding good players at discounts in free agency because they were hoarding cap space in case of an offer sheet. Even if they don’t sign Perry, Skinner and one of Henrique/Arvidsso and had enough space to make it work, I don’t think that would of dissuaded Armstrong from still putting his plan in motion. Even if the Oilers had the space the hard decision is still there on whether it’s a good idea for a cup contender to spend 7M on a couple of question marks.
I question how realistically possible it was to get these guys signed in season or get them signed for reasonable numbers in that small window between end of finals and free agency. And the big mistake in my mind is that once you had a feeling these guys might go to free agency looking for offer sheets what they should of done at that point is start shopping both players, either in sign and trades or just as rfa’s. Would have given yourself more options but also would have forced Armstrong and Ferris hand on speeding up the timeline on their plan.