I'm thinking what he means by that part in bold is that this is probably the most realistic chance in his 8 year career where he could get traded.
Outside his rookie year to year 2 transition, this is the most the Celtics have gone under a transition. For the better part of his career, its been trying to find a smaller piece here or there to remain in title contention. Now, totally blowing it up remains a very viable option when it really didn't between 2007-2012 or so.
If that makes any sense.