First, I'm worried that when Rondo comes back before the All-Star break, the team should be good enough to make the playoffs as a 6-8 seed. Goodbye lottery

Second, Rondo is a free agent after next year. Will he sign an extension or leave for a more desirable location like LA, A team that will have plenty of cash to sign him after next season concludes.
Even if the Celtics are able to draft Parker or Wiggins, will this be enough to entice Rondo to stay? hes turning 28 this Feb, He's 10 years older than those incoming rookies. Will he be willing to wait a few years for these guys to really develop and for Danny to put enough talent around them to be in contention again?
The Celtics Roster needs to be completely rebuilt, they are unable to draw big names in free agency, and I don't feel like they have the assets to pull off a trade like they did in 2008. If there was a big trade, that incoming star player would need to sign a contract extension as well....
Trade him now or potentially let him walk for nothing?