The McAdoo trade was horrible but at least Red parlayed McAdoo into ML Carr and the no. 1 pick that translated into Parish and McHale.
The Silas for Rowe trade was terrible too, but that was done because the owner was too cheap to sign Silas.
But the worst trade, hands down in my opinion, was one that is rarely mentioned: Paul Westphal for Charlie Scott. Scott played one serviceable season for the Cs and Westphal went on to be first or second team all-NBA for the next five seasons. Those of us who saw him play in the late 70s saw a very special player.For a few years he was simply the most efficient and devasting offensive player in the league. Had he played for the Cs during those years he would be remembered as the greatest 2 guard in Cs history.
IIRC, Charlie Scott's one "serviceable" season was a championship one in 1976. Scott was the team's third leading scorer, after Cowens and JoJo White, and he and White formed a tremendous backcourt.
He was having another solid year in 1977 when Red traded him in season for Don Chaney, the disgraced Kermit Washington, and a number one pick, who ended up to be Freeman Williams, a pick the Cs traded along with Kermit, Sid Wicks, and ironically, the guy that Kermit fought with, Kevin Kunnert, for Tiny Archibald, the pick that became Danny Ainge, and others.
So Red spun Scott off into what eventually became Tiny and Danny Ainge. I would have loved to have seen Whesphal as a Celtics when he was tearing up the league, but I certainly enjoyed the three championships the Cs got while he was putting numbers up elsewhere, and the one championship two years after he retired.
On the face of it, the Wesphal for Scott trade wasn't great, but Red made the most of it, as usual. Scott was at least as good a player as Wesphal, careerwise, and at the time of the trade, Scott was a proven commodity, while Paul was trying to establish himself in the league. Red made that trade to win a championship, and it worked. Scott was as big a scorer as Westphal in Phoenix as Paul became, but in Boston, Scott blended in perfectly that one championship season, playing solid defense and contributing with team oriented offense, something that Red might had felt that Westphal couldn't had done there at that time.
This trade was the classic example of trading an unproven guy on the way up for a very good one on the way down. If Jeff Green ends up putting in five or six all star seasons, while Ray Allen fades a bit and is traded for a couple of assets that help the Cs put up banners 18 and 19, will that be a bad trade too?
I'd say the Vin Baker trade was pretty horrific, and if he didn't drink his way out of $30m+ of his horrific contract, it would have been even worse.