Trading Ainge was not up there with the Robey for DJ swap, but getting rid of him didn't hurt until Ainge was in a position to trade PP just to make his point that anyone (meaning Danny Anige) can get traded. 

Bird and Red had a few things in common, the most obvious of which was the ability to see two or three moves ahead. Red made trades that resulted in McHale and Parish, RUSSELL (for the Ice Capades!) , DJ, Silas, and many more pieces of Celtics championship dominance.   Red knew how to acquire the players who could meld into championship teams.

Dave Gavitt "created" the Big East and gave the Mid-Atlantic and New England a powerhouse league for many years.  A judge of professional talent or a crafty GM he was not.  An even more absurd comparison would be Red to Fraternity Row Rick.  Pitino coul/can spot a great high school kid, but beyond that and in the NBA, he was absolutely pathetic. He thought that just bringing in as many former Kentucky players as he could was the key to winning. He also marginalized Red, which spoke volumes about Ricky's intelligence, sensitivity, or lack thereof, and his outsized ego.  In that process and with an inability to interact with adult players, the folly that was Pitino set the franchise back about 20 years. I'd vote Red (again).