The Oilers weren't any team. They had very specific vulnerabilities with their late stage organization, spending over cap on day 1 free agency, a disgruntled player who asked for a trade in-season along with a second pedigree young RFA. Both of whom showed well in final four Cup competition. And big contracts for super elites on the horizon. It's why there were allegedly 3 prospective offer sheets on Broberg and why the double offer sheets were able to come in a low level of CBA return.
We know the inaction choice led to mid-August offer sheets that worked because of the specific vulnerabilities the Oilers felt were low risk. Other approaches could have mitigated the consequences - get one RFA signed early to fend off risk of double indemnity; proactively make your best budget offer early and gage situation with a disgruntled player and second guy. If no traction initiate trade discussions to control the situation and manage return for your organization's best young NHL ready talent. Even act like they did with McLeod signing in early August and maybe you've got a chance to mitigate your obvious exposure. If the player asks are $1.3 million Holloway and $1.5 million Broberg, this is manageable money and cap wise. If they don't take the offer it's clear they aren't affordable within the cap and budget plan, so move to shop them. Having showcased their upside in deep playoff conditions, it's reasonable to think there would be a trade market which is at worst case scenario worth knowing as part of your negotiations with your two young NHL ready best talents.
There's risk in all young players but also upside. It was a targeted bet by St. Louis with low risk of assets and a walkaway after 1 year at pennies on the dollar if one or both fail. Now if as you cite the Brannstrom situation If there was a trade return of a 1st round prospect and a 1st round pick or variation of pedigree talent return (like McLeod), then that's a viable hedge versus being painted into a corner as happened with their choice to passively slow play and hope. Stranger yet when Bowman himself saw an offer sheet situation in managing a championship level team in similar situation.
The Oilers are really no different than pretty much every contender since the cap came into play. Almost every year the top teams hit July with cap constraints and still guys like Holloway and Broberg always either sign cheap or it takes till the end of the summer.
And I don't actually think a proactive trade would have been much better. Broberg effectively got a decent 2nd, a 3rd and a prospect that we know here is actually trending quite well. Do you think any team gives you more than that if they also know the guy is looking to get paid. As I said Ottawa had to let Brannstrom walk with a $2M QO. CBJ let Boqvist walk facing a QO of $2.6M. Yes he has injury concerns but this is the consequence of over paying a player who has promise that is still unrealized. Do you think some team would have given them a 1st. McLeod got way more than anyone expected so it is possible but that trade had everyone stunned. Trades like that are rare.
Holloway may have gotten a second from someone, but again its not so clear. And I recognize that there was a rumour about Buch, but we don't know the details and that deal would have been strictly short term and would probably have meant no Arvidsson or no Skinner. So what is the better option:
Buch for one year vs Skinner, a 2nd, 2 3rd and Fischer. And Skinner may re-sign cheaply.
It of course depends on what they do with the 2nd, how Fischer turns out and how Skinner plays. But it is not a no brainer.
Teh problem with the get one singed scenario to fend off the OS is that there were consequences and opportunity costs for even a $300K overpay. Bowman's comments pretty much confirmed that they knew this. That would cost them a roster spot for the whole season this year and maybe more next year. You could argue that the Oilers should never have been in this tight a spot due to moves going back over the years. But that is a different story. And I even doubt Broberg would have signed for $1.5M. His concerns were clearly also about opportunity rather than just money.