This isn't our window and I don't see any trade we can make to change that. Really the most likely result is making a misguided run at a window that doesn't exist and ruining our chance of a window in the next generation that could exist if we get lucky with the picks.
Then Boston should trade everyone that won't be around or nearly as effective when it is Boston's window.
Not necessarily. There is equity in maintaining a team that's reasonably competent while we transition to the next one.
I doubt we'd get much in the way of premium assets for firesaling IT, AB, or Horford. Thse are players who are great for the Celtics but not necessarily in demand for the teams that have high draft picks to trade.
By not trading them, we could have a team that:
a) Is much more fun to watch than whatever house of horrors we'd put out otherwise.
b) Could find itself becoming a contending team if unexpected internal development occurs (i.e. Marcus Smart or Jaylen Brown is suddenly an all star)
c) Has a punter's chance at making a run to the title if injuries break our way.
Sign Hayward/Milsap in free agency, extend everybody, and make the picks. Roll this team on until whatever combination of Smart/Brown/2017/2018 are ready to take over. That's the most likely plan right now and it's not a bad plan at all.