I have no interest in trading Rondo. He's my favorite player to watch on the Celtics. Hope he can just continue playing as well as he did in the playoffs even though that is very unlikely.
But there are certain situations that I'd have to say "yes" to.
#1 - A Superstar - Rondo isn't a superstar. LeBron, Durant and Dwight Howard are superstars. They can't win titles on their own, but simply having them with the right pieces makes you a contender. You'd have to have a perfect storm of talent around Rondo to win a title... with a true superstar, it's a heck of a lot easier. A lot of people's definition of superstar differs. I look at it as whoever is a "top 5" talent in the league. Kobe, Shaq, Duncan and KG were definitely "superstars" in their prime. Most folks (outside of Boston, at least) seem to acknowledge that Chris Paul is a superstar... which is why Danny went so hard at him the past offseason (and rightfully so). If Dwight Howard is available... I have to think Ainge will do his due diligence to see if acquiring him is possible. They have already admitted that they'd only trade Rondo if it was for a superstar talent... this is what they are talking about.
#2 - A trade for a young talent still on his rookie contract if it's part of a bigger more elaborate "big picture" plan. This one is a bit trickier. Our mythical "cap space" is actually a lot less than folks think. 25 million doesn't got very far when you have the option of bringing back KG, Ray, Bass and Jeff Green using bird rights (and exceeding the cap to do it). So... if Ainge is getting really creative and thinks shedding an additional 5-6 mil by trading Rondo for a young talent will help... then maybe you do it.
Example: Giving you a crazy example: Say Ainge had some grand plan involving signing Deron Williams (best unrestricted free agent available). Trading Rondo for a player under rookie contract could potentially make sense. Off the top of my head... what if Sacramento decided they didn't want to deal with DeMarcus Cousins despite his incredible talent (21 year old 7 foot 280 pound big man who is already an automatic 20 point, 11 rebound, 2 block guy) ... Cousins makes less than 4 mil next year. Rondo makes 11. You'd free up an additional 7 million by doing it... which means you now have 32 million in cap space. Give KG his 8 mil. Give Jeff Green his 5 mil. Give Ray his 5 mil. You now still have enough money to give Deron Williams a healthy contract and march out the following lineup next year: PG - Deron, SG - Bradley/Ray, SF - Pierce/Jeff Green, PF - KG, C - Cousins... It just gives extra flexibility.
Alternatively... Ainge apparently had interest in trading Rondo for Stephen Curry last year and Golden State turned us down. I love Steph Curry. His injury issues are bothersome, but I think he's an incredible shooter. Once again, Steph makes under 4 mil next year... From a pure talent standpoint, I'd probably rather have Rondo. But if trading Rondo for Curry is going to give us the flexibility to go hard at a restricted free agent like Roy Hibbert (while keeping Ray, KG and Jeff Green)... MAYBE it makes sense.
Again... only if it's part of a "big picture" move. I see it as a 2-for-1. Would I trade Rondo for Steph Curry? Prob not. But Rondo for Steph Curry and Roy Hibbert?... probably. Would I trade Rondo for Cousins? Probably not. But Rondo for Cousins and Deron Williams? Absolutely (if KG can be a mentor for Cousins). THere are a lot of players you'd have to think hard about... Kyrie Irving, Ricky Rubio, maybe a player in the top 5 (if Ainge REALLY covets someone)... Arguably even someone like Brandon Jennings if it's part of a brilliant grand scheme (Jennings makes 3 mil next year... he's 21 years old and showing signs. Certainly still has potential). It's all about context. Again, I absolutely wouldn't trade Rondo for Brandon Jennings... but if it's some grand scheme to free up enough cap room to swallow the contract of a Al Horford or something... you think it over.