I really like Upshaw as a player, and I wouldn't be the least bit surprised to see us take him somewhere in the draft. To be honest, I think Ainge tries to trade up as far as he can for a falling Johnson/Turner/Mario kind of guy. If we do that and get a wing, or if we can't trade up at all, I think DA will use 28 or 33 to roll the dice with Upshaw.
His stock will rise a bit surely, but I still think most teams won't want to use a 1st rounder on him. Ainge might at 28 if he's pretty sure someone will at 31 or 32, but 2nd round picks have more flexible, less guaranteed contracts. Thing is, when you've 21 and you've only played less than 30 college games at two separate programs you got kicked off of, that's concerning. The multiple failed drug tests (reportedly for weed, but not confirmed) are a huge concern. Both places he was kicked out of said he had "multiple violations of team rules", something that is never a good sign. His maturity and commitment has been questioned multiple times. You can even see laziness in his best games.
Now, he's got enough talent that if he had played all year, he'd probably be right around 12-16. He's a truly elite rim protector, but he gets backed down in the post by guys smaller and weaker than him, he makes poor rotations and can't defend away from the paint, even though he's fairly mobile. His offense will be limited to P&R's and put-backs, especially at first, because he doesn't have much post game or much of a jump shot. He's quite flawed.
But still, he projects as a truly transcendent rim protector who has enough other skills to become a valuable player in this league. Considering our desperate need for a defensive presence at the 5, he could be the perfect guy to take a chance on if you feel confident you can keep him on the court and out of trouble. That's just the problem though, guys who have had THAT many issues before they even get to draft night don't often turn their behavior around. Take him as late as you can, but if it seems someone might take him before us at 33, I would probably pull the trigger at 28. Assuming the interview goes well, and it seems like he's not a lost cause