There are two issues with the pick he got back. First, it's protected multiple times over and the draft position for the pick will be determined by the performance of a consistently good team. The second issue is that the Senators could potentially have to wait until 2025 to use the pick. I suspect there is a reasonable chance that the pick will be traded before then. If the Senators are pushing at the deadline, it doesn't help Dorion to hold on to a pick for his possible successor to use - What helps him is to acquire a rental who can help the Sens push for a deep playoff run.
I agree. I was surprised Ottawa got stuck with having to take the worst of the two picks. The condition should have been that Ottawa gets the better of the two picks unless at least one of them is in the top 10. Only then would Detroit get to decide whether to give Ottawa their own 2024 pick or the one they get from Boston. I saw a similar condition on another trade, and I thought it would have made sense here. Fairer value for Ottawa while still ensuring that Detroit doesn’t have to give up a top-10 pick unless they luck into two of them.
But if you're right about using the pick to acquire a deadline rental, it probably doesn't matter because most deadline rentals are traded for late 1st-round picks anyway. But in that case, why not just keep Debrincat as your rental? Cap space, I guess. Deadline rentals usually come with a reduced cap hit. Of course they have to get into the playoffs first, which could be more difficult without Debrincat.
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