And yet it took beyond Yz's tenure for TBY to win. They built that team through the draft.

Holland took over in EDM closer to contention than Yz did in TBY. I doubt Stevie is going to try to jumpstart the Wings by trading away core talent to bump up their draft order. He built a perennial contender in TB with astute picks in the mid to late rounds. He values a winning culture and scouting acumen. So the chances of him losing a trade of a quality player like Mantha for the likes of Neal+ to improve draft ranking is less than slim to none. It's not like he traded Stamkos or St. Louis at the peak of their powers for 10 cents on the dollar. He extracted the bulk of almost every player's value before winning the trade that sent them away. Except maybe Gudas, and that's barely a blemish on his record.