Rondo has not given indication of 100 percent he is going to resign long term with the team. He has actually stated that he is looking fwd to the FA process.
Also it doesnt help that we will still be in rebuild mode next season. It's a risky situation and I dont think Danny takes a chance of letting Rondo walk for free like the lakers did with DHoward.
I don't think Ainge needs to make a big move before Rondo enters free agency. I think Ainge can do it then. During free agency. I mean, it would be nice if Ainge was able to do it before-hand but I don't think it is absolutely necessary. I think Ainge can make that big push during that FA and convince Rondo to stay there and then.
Similar to how Pat Riley went into 2010 with D-Wade expiring but knew Miami had lots of cap space to convince a second star to come play with Wade, and, that if he got that 2nd star, then Wade would stay.
I wouldn't be afraid of that type of scenario. It doesn't always play out in the team's favour but Ainge has loads of assets in terms of picks, prospects and cap flexibility so I really like his chances of being able to make a big deal and convince Rondo to stay.
Unlike say Toronto and Chris Bosh, who in 2010 had no cap flexibility, few prospects on their books (Bargnani?), hardly any trade assets (Calderon?) and no extra draft picks. Meaning Toronto had no hope in hell of getting a 2nd star to come to Toronto to play with Bosh ... meaning they had no hope in hell of convincing Bosh they could be anything better than the 40-45 win team they had been in recent years. Making it pretty much a certainty that Bosh would leave.
If Boston was in a situation like that, like Toronto and Bosh, I would say trade Rondo ... but they're not. They have terrific trade + free agency options. So I am confident enough in Boston's flexibility to be able to pull off a scenario like that.
And even if worst case scenario comes about and Rondo leaves, well then that just ushers in a full rebuilding process. Same destination as originally wanted in trade above. And Ainge can build the new title contender that way. I really do not believe that Rondo leaving and Boston getting nothing in return is that bad a scenario. Boston would still in a very good long term position due to their cap flexibility, prospects, trade assets, future picks and increased likelihood of getting high draft picks in immediate/future seasons.