I have been wondering, what's the true value of Hoffman? He's a one trick poney. Slow, weak defensively, but can put up 40-ish points with PP time. Questionnable reputation, though did not seem like a cancer on the habs. He's just there.
What you see is what you get, the whole league knows him well. Could he return a 5th in a trade? Would he even be picked for free on waiver? I would gladly pay the 5th we acquired in the Bonino salary retention trade to see him go and give his PP time to others.
I think trying to pump up his value by trade deadline is possible, but not to a very high level. For what, a lottery ticket like Gurianov? A 4th? Trying to get an asset is great, but it sounds like the sunken cost fallacy. And it can backfire like it did with Drouin. I was fine with the salary, but 3 years has always seemed too long at that price for my taste.