I'd rather be wasting money in 22-23 when we don't have a chance at a Cup than in 24-25 or 25-26 when hopefully we do.
The ideal thing with Dickinson/Poolman would just be to package up some picks and prospects with them to get the full tickets out of here to an Ottawa or Arizona. Dickinson is useful enough that some team might take him if we give up a 3rd.
Absolutely. It's another version of the Beagle / Roussel contracts heading into this season. Like yes, they're bad, but it's over soon enough, and the team isn't contending during that time. If things go better than expected in 2023-24 and the team is a legit contender, then sure, move Dickinson at the deadline with a low pick to a floor team who will be happy to get an asset for an expiring contract.
Poolman is definitely worse because he's not a roster worthy player and he has an extra year of term (how??), so if someone is willing to take his contract now with the hopes that he can bounce back into something, then that would be great. Maybe a dumb team with a bad defense like Edmonton or Philly would bite. Or a smart team that's rebuilding, like Anaheim or New Jersey.
As has been discussed here many times, good GMs can create something out of nothing based on their team's position in the rebuilding cycle by taking on players like Poolman with any excess cap space for assets. Would've been nice if we had done that vs just signing them to bad deals, but hey.