For starters, trade away KG to a team with some Cap Space for someone who hurts they're cap (a player with a BAD contract, but still has to play)
How would trading an expiring contract for a player on a bad contract help our future?
I don't know about a "bad" contract, but a player who still has a couple years left who is overpaid could be worth it if we get a good pick as well. The salary we'd be taking on would effectively be "renting" our cap space for the next year or two, since we most likely wouldn't be using it on any big name free agents anyway. Getting as many picks as possible in this upcoming draft is a really good idea.
It depends upon whether we can convert the picks into building blocks. If they're used on role players / non-starters, it's counterproductive, as we're tying up cap space in guys who aren't part of the future.
Trading for picks is not counterproductive at all. What´s the alternative?
Should we use our cap space to sign the Celtics equivalent of Charlie V and Ben Gordon, or do you think we have a shot at Dwight Howard?
Our top priority in rebuild mode is to get high potential players, not the scrubs other teams didn´t want.
This is about taking back control over your own situation.
Draft picks provide both flexibility and the chance at a future franchise cornerstone, they allow us to package them and trade for exactly the kind of player we want instead of taking what´s available in free agency. Think back of the days when we had cap space but no chance at winning it all. No real impact player wants to sign for a Celtics organization that has no chance at the championship.
Just take a look at the Chris Paul saga. Paul didn´t want to sign an extension with us although we have the big three, what do you think will happen if they´re gone? Instead, he picked up his option for the Clippers. Think about that, the best PG in the league chose the freaking LA Clippers over the Boston Celtics! If we want to get back to the top we have to do it like we´ve always done it in the history of this franchise: through trades and the draft.
Red was willing to trade Ed Macauley for a pick. He traded the first overall pick for the third pick and an underachieving center. He picked a player at #6 who would join us a year later. There was a pattern to this madness, as he always made his own luck instead of waiting for the leprechaun.