Re: IT plus Cousins, the answer is you do everything in your power to add the superstar this team desperately lacks and figure that out later. If it means trading IT, fine. He's not nearly as good as Cousins.
Flex, this is a fun stroll through a fantasy off-season. But I emphasize fantasy. I really don't believe Butler or Cousins are changing teams this summer, unless somebody offers a top 3 pick. Full stop.
I believe we need to set our sights on players that other teams don't necessarily covet. Buy-low options. Less talked about trade targets. I think the Celtics are still a few shuffles away from the opportunity they need to add a couple core pieces.
So ask, instead, how will Danny Ainge look to further convert picks and young role players into tangible assets this summer?
I'd agree this is an ideal, not a realistic course of events. Butler I think is the most unlikely. I still believe in the Kings' calamitous front office to trade Cousins this offseason and I don't see why we wouldn't be a) a desirable destination for Cousins and b) a desirable trade partner for Sacramento.
Also, if we do add Cousins, I think we suddenly become a legitimate player for a number of free agents. To me with Cousins aboard we'd be as attractive as LAL to Love if he were to leave Cleveland.
Further on Cousins and the implications of landing him: (speaking in general) I'm a bit concerned with the notion that the Celtics should pay Khris Middleton $15m annually without at least one star already in place. If we had Cousins, adding a guy like Middleton or Draymond Green for that type of dough makes complete sense. Could we send Sacramento:
Olynyk
James Young
Tyler Zeller
2015 BOS 1st
2016 BKN 1st
2017 better of BOS/BKN 1sts
for
Cousins
Sign Middleton to 4 years/$60m (Bucks won't match that, will they?). Sign Pero Antic to mid-level money.
Smart/IT/Pressey
Bradley/Evan Turner
Khris Middleton/Jae Crowder
Sullinger/Bass/McCullough/Jerebko
Cousins/Pero Antic
Me likey. But again, as you said, tons of ifs.
On buy-low targets: Are we talking about a guy like Middleton or a guy like Moe Harkless? I wouldn't mind adding a guy like Harkless for the right price but I remain unconvinced that we'll have to visit that last resort. The Celtics have an insane asset pool right now. I can see us whiffing on the top tier of available free agents/trade targets: Cousins, Aldridge, Gasol, Love, Kawhi, Butler, DeAndre Jordan, Millsap, Monroe, etc. I can't see us whiffing on the next few tiers: Middleton, Draymond Green, Tobias Harris, the Lopez twins, Asik, Danny Green, etc.