I gotta think the C's sign Ray to a 2-3 year deal after this season. My reasoning is that Garnett is up after 2012. Pierce will likely be reupped for a couple seasons. These guys can fade into retirement together.
But they probably have 2 more good seasons left in them and with the emergence of Rondo as a top point guard this team can still be relevant.
Plus they will probably play in the regular season like the Spurs, ie a repeat of this year. Which will put them around 15-20 in the draft over the next couple years. This is a draft area that Danny does good in.
This gives Danny the ability to make some draft choices. Hopefully some of those guys turn into legit stars, if not you can build them into a couple starters, potential guys, and role players. Remember that this is where Danny was drafting when he built the core of the Allen and Garnett trades.
I think even with these guys in the twilight of their careers over the next 3 seasons, that they are a more relevant and dangerous playoff team then the early-mid 2000 teams with Paul Pierce and no one else.
That or you sign and trade Ray for someone who is younger and makes an immediate impact. You don't let Ray walk away for nothing. Without Ray this team is probably drafting 10-15, and the difference between 10-15 and 15-18 in the draft is a crap-shoot anyway.