I'm not stoked with the return for Jake but when it's widely known a guy isn't negotiating and is intent on testing the market you're just kinda f***ed. The reason Rantanen went for a much better return is because A. he's a much better player than Jake and B. he's been in negotiations the whole time, so wherever he goes is gonna feel like they might be able to work something out.
As I understand it, Dubas and Jake's camp met during the summer and there were some negotiations, the two sides weren't close, and Jake/his camp got all flustered and decided that's that, he's going to FA. I don't blame him, he wasn't ever gonna get a colossal deal here and this team's toast. And yeah, I wish Dubas would've gotten more by trading him that summer when it was clear the two sides weren't gonna bridge the chasm, but it is what it is. /shrug
Honestly couldn't give a shit less about Jake or the trade anymore. I barely care about the EK deal and losing the 1st that could've been Dickinson, Buium, or Eiserman, on top of now having to retain and find a taker for EK since that experiment failed is much, much worse situation than the Jake deal imo.