GrantLemons
Church of FYOUS
As I've said elsewhere I believe Dorion chose to "Swing for the Fences" in 2017 because he knew the team was going to be decimated for financial reasons in subsequent years (I suspect he knew they couldn't sign EK and eventually Stone and others, including Duchene). It was an all-in, one shot attempt.
Poorly timed in my opinion and whether he should have known better is a good question.
Dorion had long coveted Duchene prior to actually pulling the trigger on the deal. To me, it feels like Dorion finally caved and gave in to Sakic's crazy demands after he had pissed off and burned the Kyle Turris bridge during their contract negotiations, and subsequent involvement in trade talks. I think he felt like he had to move Turris ASAP, and was also potentially (likely) getting pressured by the owner to get a deal done.
I seriously doubt there was any sort of plan in place when that deal was made. They f***ed up the Turris negotiations (much like they are f***ing up the Stone/Duchene negotiations), and made a quick trigger move that was a gross overpay to get Turris out of town, and Dorion would "get his man".