There were a few moves that seemed questionable, but they always sort of worked out. For example, the Celtics gave up three first round picks in the 79 draft (3, 9 and 21 - eventually Bill Cartwright, Larry Demic and Sly Williams) to acquire Bob McAdoo, who didn't do much in Boston. However, they used McAdoo to get the two first round picks in 80 (1 and 13) that were then traded for Parish and McHale. So Red made it all work out in the end.
A lot of people mentioned Ainge for Pinckney and Kleine, but honestly, at that point we had Reggie and Shaw to play the 2, while Bird was out for the season (89) and we needed frontcourt help behind the aging McHale/Parish combo. We should have gone younger with it if anything, but both those guys actually gave us decent service.
Other than that, no really bad trades I guess, just some poor draft choices, though that happens to everybody. We gave up the second round pick that turned out to be Gerald Wilkins, a pretty good player but not a world changer, to get the Knicks to agree not to resign Ray Williams. In 85, we traded up to get Sam Vincent and gave up the pick that turned out to be Terry Porter, another pretty good player who would have helped us in the late 80s more than Vincent did. In the Maxwell for Walton trade, we also gave up a first round pick that turned out to be Arvydas Sabonis, though he didn't come to the NBA until more than a decade later.
