They tried desperately to consolidate picks in a deal for a higher pick to draft Winslow, and we all know how that worked out. It was a massive overpay but it didn't matter because you can't force other teams to deal with you if they don't want to. We ended up getting some promising players with those picks, but we only have 15 roster spots and you can't have that many rookies coming in every year unless you are trying to tank.
I think at some point, probably next year, the Celtics may need to have a "step back" year where they play some of the younger guys for better or for worse.