Oladipo is a very good player. He is like last year's version of Jaylen Brown good. In a normal market, he is probably worth Brown money or maybe, or so slightly more. But, in next year's market, with most of the big names re-signing this year, so not available, and lots of teams with bunches of cap space, Dipo is probably going to be offered a max contract.
Is he worth that to the Celtics, who would need to re-sign him after trading for him? They're going to go into the luxury tax for the next two seasons no matter what unless they salary dump Kemba, which won't happen. Re-signing Oladipo after trading for him probably means repeater tax status as soon as possible.
Again, is he worth it? Does he put the team over the top and into instant contender status? Will he even re-sign here given the report he wants to play for Miami? And if not, does it make sense to make the trade in the first place?
If Ainge could land Oladipo for Theis and Edwards and an unprotected future 1st...or Nesmith and Langford and a lottery protected future 1st...and Dipo agrees to extend before the trade, then I do it. I don't see the trade being worth using that TPE for a rental that won't agree to extend and has said he wants to play in Miami next year.