Rozier and picks doesn't get us nearly high enough to get any of those players, so this seems like an exercise in futility.
I frankly disagree about Rozier. Entering is his 4th year, he’s still cheap (will make less than any of those players next year). The PG class this draft is incredibly weak. Teams that need PGs include Orlando, Cleveland, Clippers, and the Knicks. He’s clearly proven himself to be playoff starter quality. At his age, there is likely more growth to come, and given his restricted free agency/extension eligibility, a team trading for him could easily control him for the next 5 years.
The Clippers have picks 12 & 13. They seem to be a perfect fit in terms of need for Rozier. They need a PG, are not looking to do an extended rebuild, and have cost considerations this upcoming season for which Rozier’s $3 million salary would be quite helpful. They even have a trade exception that fits Rozier which expires at the end of June. So getting to 12 doesn’t seem impossible — and considering George Hill was traded for #12 just two drafts ago while heading into unrestricted free agency (or Jeff Teague, depending how you want to view that trade), it doesn’t seem like my green-colored glasses are on. And given that, someone like the Knicks trying to outbid the Clippers for Rozier is also not far-fetched, nor is combining #12 with #27 to move to #9.
The wildcards are two things, primarily. Firstly, how far does a big that Ainge wants fall? (If the bigs in this post are all gone by #6, it could be too difficult indeed to get a Rozier-centered deal done). Secondly, how high does Trae Young go? I think it will be difficult for a team looking for a PG to consider Rozier while Young is on the board (even if I’m personally not a Trae Young fan, I get the appeal). So as long as he’s available, teams that might be interested in Rozier won’t move. And these two are correlated — the later Young is picked, the more likely it is all the bigs are gone.
Maybe it’s not likely that a deal gets done, but it isn’t nearly as crazy as you seem to think.
And ultimately, if Ainge can’t use Rozier as the primary piece of a deal to break into the top 10 to get a big (or Doncic, but I need to stop dreaming) then he really should just hold onto Terry. There’s enough uncertainty about our PGs heading into the summer that just moving him for a mid-first isn’t enough reward for the risk.