KG is in fantastic shape and is tall. No reason he couldn't have a Kevin Willis-type career (playing until he's in his 40's off the bench). Ditto for Ray (though not as tall).
But as we're learning in this thread, the cap situation makes it all pretty hard.
Imagine a 2nd unit with Ray and KG plus a vet PG and 2 young athletic freaks at SF and C. That could run another 2-3 years after this one easily. Unfortunately, our current young players are 2 SG's and a PF...go figure. KG will probably retire a starter, though. So scratch that part...
Jeff Green falling in love with the C's organization and committing to the Green for a discount would be a tremendous part of this mid-term plan. Keep starting Pierce, and let JGreen, Ray, and KG lead a 2nd unit in a Hubie Brown-esque rotation, while Pierce and Rondo lead the starters.
So the holes I see going forward are:
Starters: SG, C
Bench: PG, PF, C
So if J3 is able to play backup PF starting next year, that woudl be absolutely fantastic. If either Bradley or Moore can become competent backup PG for 12 minutes behind RR, then we're in pretty good shape. And if Steimsma can play a bit of bench C, even 3rd string, we're absolutely golden, needing only a starting center, SG, and more depth at the big spots that could perhaps be filled in the draft.
If there is any wild chance that a SG could be picked up in the draft to start and play 18-20 min ahead of Ray, then we don't need to spend cash there. Then all we really need is Howard.
Rondo/Bradley?/Moore?
YoungEnergySG/Ray
PP/JGreen
KG/JJJ
DH/SomeBigGuy/Steimsma
In this deal, everything hinges on Howard. He gets the top money ($14-15M?), then JGreen ($4M plus incentives?). Then I think Ray and KG get sweet talked into splitting whatever is left to keep going for titles for 2-3 more years (until KLove is available again?).
So this is the pitch to DHoward, I think: With DH, we could put a team out there of proven pieces that fit together and know how to win, with Ray and KG in diminished roles in the short term and the youth movement of Rondo, Green, JJJ, and the draft picks for the longer term.
We've got it together, folks. Best run franchise in the league right now.