A lot will depend on how the ping pong balls bounce and whether LeBron bails out of Cleveland for LA, but the East looks like Boston’s to lose next year, so keeping Terry and making a legit run at a title is certainly appealing. A regular season rotation of Kyrie, Jaylen, Tatum, Hayward, Al, Smart, Rozier, Morris, Semi, and Theis plus a ring chasing vet or two is insanely deep and allows Brad to keep the starters fresh for the playoffs. It’s probably not maximizing the value of Rozier, but with all the extra picks Danny has stockpiled, it’s not like keeping him limits the Celtics going forward. There will be plenty of cheap, rookie contract talent to fill out the roster.
All that said, if forced to choose between keeping Smart or keeping Rozier, I have to lean to keeping Smart for two reasons. First, he seems likely to be cheaper, and thinking ahead to a world where Kyrie, JB, and Tatum are getting new contracts, the difference of Smart at $8-10mn per and Terry at maybe $14mn+ means a lot for luxury tax purposes. And second, Terry has much more trade value vs. whatever Smart might return in a sign and trade. So, it’s not as much Smart > Terry, but Smart + trade return for Terry + lux tax savings > Terry + Smart trade return.