This almost feels cooridnated now, and this latest article from The Ringer pretty much spells out that he's gone.
In this latest one, while staying noncommittal to Boston the entire time, he talks about everyone here is talking about a championship, but he's worried about growing his own game still, with the implication being he doesn't feel he can reach his ceiling as long as he's playing next to Tatum. It even gets deeper where he talks about a lecture he had at Cal that stuck with him and affected his play, a lecture about black athletes being seen as commodities, and that literally just a couple months ago he was having similar feelings.
This guy wants his own team, plain and simple. Combine this with his feelings about the area, I think the probability is higher than ever that he doesn't re-sign.
There will plenty of fans I'm sure that will come out now and say I'm reading too much into things. To which I would counter and say you're running out of time to ACTUALLY read into this stuff. Jaylen's telling us without spelling it out - he wants out.