I don't think it really mattered when you traded Kakko. Waiting 10 more weeks, you think his trade value would skyrocket after 6 mediocre years? Seems highly doubtful to me. In addition to that, after the past few days with the scratching and the comments by Kakko, which were not out of bounds BTW, it became a semi-untenable situation. Plus, Drury is terrible at his job and in over his head, I don't think 10 weeks would have changed how Drury would maximize his return.
If they held and waited, I would have been fine, if they dealt him now for maybe 3 picks once they deal Borgen at the trade DL, that is fine. I really don't see this very different landscape in 10 weeks, and I don't see Kakko going off here during that time either. I could certainly be wrong in my thinking, but that's where my head goes. Now that the trade is done, it's an unanswerable question though.