I"m a loyal rider of team tank, but I'm pessimistic about the future, even if Benning is gone soon. A new GM would have to be aggressive and creative in order to dump what needs to be dumped and acquire enough young assets soon enough to build a contender around the group of four.
Realistically this isn't very likely.
Think about the timeline:
Benning has to be fired. This could happen at the end of this season but it's unlikely. So we could be stuck with him for 2-3 more years.
The new GM is hired.
We don't actually know if this new GM is going to be competent or not. Sure, they would likely be better than Benning simply due to the fact that it would be extremely hard not to be, but this doesn't mean that they'll actually be good.
If we assume the GM is good, they will immediately realize that they need to clear the bad contracts and filler players to build a stronger supporting cast round Pettersson, Boeser, Hughes and Horvat.
This job is much easier said than done. It's unlikely that all of them can be traded off and therefore we will remain very limited in cap space while not having a strong supporting cast.
It's much more likely that we are doomed to wait until the contracts expire. At this point the core are in their mid-late twenties. This is their prime. They are all on their second contracts and any cap space free'd up by our expiring bloated contracts are eaten up by the core's raises.
Now it's up to the new GM to surround them with enough talent to contend. Again this is easier said than done because we won't have many assets to acquire talent with. Honestly it will depend a lot on our drafting and if we can have ELC players contributing for more than what they're getting paid.
Either way even though our core is very young and we look to have them for 6-8 years including their prime, realistically we will only be in a position to contend for 2-3 years of their stint with us.
If I had to rank the scenarios, i'd put them as follows:
Most likely: The primes of our core are wasted with a mediocre supporting cast. If they all peak at the same time we could make it to the second round and put up a good fight, but it wouldn't be enough to even make the WCF. This scenario occurs if Benning remains our GM or if the new GM isn't skilled enough to fix his mess quickly.
Somewhat likely: The new GM attempts to contend but fails due to the handicaps left behind by Benning. The core is sold off when they are around 29-30 years old for prospects and picks. The new GM begins his own rebuild.
Unlikely: The new GM is able to shed the poor contracts, acquire value in the draft and free agency, and can build a solid supporting cast around the core, who then can compete for a Cup.
Simply put, I think there are only a few GM's in the league that are capable of cleaning up Benning's mess in a timely manner. I think it's unlikely that our replacement GM has that level of skill.
I think it's much more likely that the only way to clean up Benning's mess is to sell off the core and rebuild from scratch, allowing all of the bad contracts to run their course and to draft well over the next several years.
The most annoying part about all of this is that we can all see it coming, but we still have to wait several years for the organization to realize that they're headed to a mediocrity purgatory.