prediction
I look for Danny to trade one of Smart or Rozier on draft night. I think the Clippers or Hawks could use Rozier
Then Danny drafts Divicenzo and Spellman with the 2nd 1st
You can't trade Smart because he is an RFA. Trading Rozier for a pick is not wise as the draft pick won't help us win a championship next year as much as Rozier will. And Rozier is on a good contract.
Prediction: Your prediction doesn't happen.
I say yes. Trading Smart would be a little more tricky but Rozier is a possibility
he is going to be in the same situation Smart was this season and looking for money and potential starting chance
I can't see tight Danny losing both of his reserve/semi starting guards for nothing (but also I doubt wants to get in a battle to match/overpay)
Divicenzo and Spellman will help right away. They are not 1st year clueless prospects. They have been really well coached, won a championship this past season. Their skillset would fit right in (Divicenzo shooting/defense, Spellman shooting for a PF/C/passing/team defense). Already have NBA bodies (spellman could lose a few pounds)
First, trading Smart won't be tricky, it will be impossible. He becomes a free agent the day after the last NBA Finals game and becomes a RFA once Boston extends the qualifying offer. The only way to trade him would be after July 1st in a sign and trade. He can't be traded on draft night.
Second, whether Spellman or Divincenzo come into the league ready to play or not they won't be playoff hardened good and won't be able to contribute anywhere near as much as Rozier. You keep Rozier, win the title and let next offseason take care of itself.