It's about hitting timings, imo. Jake's gonna decline sooner than later, and as soon as Sid starts to slow down, Jake's gonna drop off as well. If you spend the next six months seeing what you can get for Jake around the league, I have no doubt there's a few deals out there that make sense. Either from the standpoint of the here and now, or the standpoint of trying to kickstart the window. You cannot pay the guy $9 million AAV and give him a clause that's like 8 spots he'll accept a deal to. I think that'd be flat out dumb, and the team would end up regretting it in short order when it screws up their cap structure and costs them a shot at a legit gamebreaking talent in FA, or when they try to move Jake once Sid's career wraps up in a few years.
I'm not saying dump Jake for scraps. I'm saying make calls around the league to gauge interest and if there's a deal that lands you a young roster player with potential, a good/great prospect and a top-10 pick, you make that deal and don't even look back imo.
With big value players, you always gotta try and deal them a day too early as opposed to hanging onto them a day too long. With Jake being at a crossroads this season in terms of needing a colossal extension, now's the time to be aggressive and move him, because once he puts pen to paper, that's that.
-edit- What's the huge concern here? This team's gonna miss the playoffs?
This team's cooked, they haven't sniffed the 2nd round in half a decade, and the rest of Sid's career is just gonna be about keeping up appearances. At least if you deal Jake for a haul as part of a bigger picture, you have a shot at extending the window or expediting the process of building the team back up once the era officially ends.
They should've moved Rust at the deadline before the summer where he was up for a new deal, too. His value was at its highest and they probably could've pulled off a deal for a younger, up and coming prospect and a 1st (well, somebody, probably not Hexturke), which could've done wonders for extending the window, which seems to be the big thing surrounding this team anymore.