Terrible idea, for several reasons.
First of all, like Meadowlark_Scal said, you are wishing you can get a couple of stars who can be better than Rondo and Green in what, 4-5 years? Not the safest bet, and unless you get Wiggins AND LeBroid (yuck) as a FA, you're set for fail.
Then, you're trading Rondo at his lowest value (post surgery) and not allowing Green to pump his own value through playing as the 1st option on a team. Horrific timing. If you're trading those two, you need to maximize the return. Drummond could develop into the next Karl Malone, but to get him you have to give a lot more because his potential is at a maximum right now. Not the best deal, IMO.
We have a young core, with an All Star and a probable All Star who have at least 6-7 prime years in them. Ainge has traded Doc, KG, The Captain and the Jet to develop his young players and use them plus future picks and expiring contracts to get one or two All Star caliber players.
What I'd do is try to trade Humphries to Philly for their 2014 2nd rounder and a TPE. They are under the salary floor right now, and Hump's contract could be very valuable at the trade deadline. But Celtics need roster spots and the TPE could become gold around next year's Draft. Then, trade Bass for a younger, cheaper player (i.e. Bass to Minnesota for D. Williams) or better, for expiring/TPE + low picks. Move the China Boys for future protected 2nd rounders or a little TPE. Roster could look like this:
Rondo/Bradley/Pressey?
Lee/Brooks/Crawful
Green/Joseph/Bogans/Mitchell?
Sully/Wallace
Olynyk/Melo/Iverson
You probably cut Joseph and/or Mitchell or trade them for peanuts if they can show some value. Trade Bogans' expiring at the deadline for something useful. You also hope for Wallace to regain his level and show himself as a 1st forward off the bench.
This way, around the 2014 Draft, you have a 12M TPE, 2 first round picks, Wallace, and some young assets to bring another Star to this team, who could compete for the playoffs as soon as the 2014-2015 season.
All wonderful in theory, but putting an All Star around Green and Rondo isn't getting us anywhere. We just had 2 all stars next to them- 3 of them at one point and we won a single championship. KG's injury hurt that, but neither Rondo nor Green are franchise level players.
That's the point of this trade- you're blowing it up for a real shot at some franchise players and a draft that's a once in a decade opportunity. The timing is perfect, we are at a crossroads and we can re-tool or blow it up and rebuild from scratch. We've got a few young nice pieces in Sully, Avery, Olynyk. As well as some serious assets in picks+ solid starting small forward + a bench All Star in Rondo. Now if Durant or Lebron were free agents now then well, we've got Rondo and Green. A little work and we may have a real contender.
This draft is that loaded that getting a top 3 pick could greatly improve our chances at a championship.
I always use the example of looking at the past 50 years of NBA champions and teams that made the NBA finals. Even 25 years of history shows the relation to drafting a genuine superstar and making the finals/winning a title.
Go back and find me a finalist team that didn't get there without a home-grown/home drafted kid that was a top 5 pick (or was picked higher in the lottery due to being overseas or young of top 5 caliber). The Pistons did it.
Find me another team.
You can't because only one exists.
The talent in this draft is that serious that I feel we need to put ourselves in the best position to draft one of those 3 guys. We are the kind of organisation, with Danny Ainge in charge, that is good enough to put the right support cast around such a player. If we miss out, then well that sucks, but we took our shot and will still have a good player of potential All Star level, with plenty of cap room and picks/assets.
Who knows what Rondo will be like after the ACL injury? He already can't shoot. What if his athleticism is effected? If you can trade a recently injured Rondo with only 2 years on his deal at the beginning of a rebuild for Drummond it's a no brainer.
Since when is Jeff Green a probable All Star? He's a third option at the moment. Great complementary piece on a team like Rondo, Josh Smith, Monroe but as the go to guy? I mean the potential is there but we still haven't seen it.
Anyway, Meadowlark and yourself have this wonderful dream of one day being a real contender with Rondo, Green and another All Star. Those guys are not franchise players. If you put Durant or Lebron (Wiggins or Parker?) in between them then they have a shot. Jesus they put Lebron with Wade and Bosh and they've been lucky to win 2 out of 3. They guys they played? Built around Tim Duncan- a number one pick. Funny how 4 of the 6 most important players (the guys effecting the outcome of the NBA championship were picked 1-5). Tony Parker in the top 20 at the time was high for a European point guard. The Spurs have Tim Duncan. They have their Rondo in Parker and their Green in Leonard. Unfortunately we don't have a Duncan. 2014 could have one, it could also have 2 other guys like Pippen, Carmelo, Pierce, Tracy McGrady etc...
I mean it's great to say 'lets not gamble on the lottery/draft' yet you're fine with letting Rondo get to the end of his Celtics deal-after he's suffered through the torment of a terrible team, whilst his body takes more punishment because he's got too much pride to not go hard now he's the team leader- and then hope that's he's still okay with the organization.
Then you've got to sign Marc Gasol or Kevin Love- away from their current franchises and then on to yours ahead of the competition like the Lakers, Knicks, Clippers, Miami Heat, Nets, Bulls etc...all big market franchises.
You're assuming that Rondo and Green will be better and get to an All Star level. What if Rondo never makes another All Star game? What if Green is an 18ppg, 5 assists, 5 rebounds guy like Pierce?
Are Rondo and Green giving us a real shot at a title against OKC, the Heat, The Pistons, Cavs with Kyrie and Andrew Bynum (among others)?
I really don't think so.
You claim that trading Rondo and Green for Drummond, Pope and a treasure chest of goodies is 'bad timing', but the Pistons have the chance to win now and be a serious contender with additions like our guys. We unfortunately don't have a chance in hell of signing anyone like Smith and Monroe. While we wait for the chance to do that, Rondo's contract is expiring as is Greens.
I think it may be the perfect time to trade Rondo and Green because they are NOT taking us to banner 18 and we could get back talents like Drummond and Pope and the rest- right when we need to lose games to get a better shot at the 2014 lottery and potentially draft a franchise player. NBA championships are won by franchise players who are surrounded by All Stars and excellent role players.
How do those championship teams get those franchise players? They draft them.
History proves this. The Pistons are the exception to the rule but it's funny isn't it?
There will be a few franchise players in the next few years. NBA and basketball scouts worldwide are touting the talent in next years draft as having multiple forms of 'franchise' potential- the stuff of NBA champions. So rare that when it comes around, the odds of the team that drafts them winning a championship-or at least making the finals goes up an amount that is undefinable. Whatever that number is, it's far higher than acquiring a player through free agency.
I highlighted your last part because that's exactly what we'll be doing. Bowing out in the first round, not getting any picks, losing out on major free agents, watching Rondo walk or get injured with his style of player.
I mean I don't know about Rondo and exactly what round we'll exit the playoffs.
The important part is that for you and Meadowlark, it's fine to make the playoffs as long as you don't stink. For me, it's never fine unless we are successfully building a team that can truly compete for a title with the other 3 best teams.
Not gonna happen with Rondo and Green. Never.
If we get a top 3 pick in 2014 and land Wiggins, Parker or Randle? Much, much, much more likely.
History proves this.