I love all the Boston teams, though I tend to favor the Sox more than the other three.
That said, I'd definitely rank them:
Pioli/BB
Theo
Ainge
-I think it's a 1A/1B case between the Pats and Sox (with a slight edge to the Pats), and the reason I say that is that Theo's master plan is truly just taking shape. Granted, he's doing it in an uncapped league, but the '$100 million player development machine' has truly changed the culture of the Sox organization. Not only do they have a TON of flexibility now, they have BY FAR the best depth in all of baseball (half the players on Pawtucket would be on MLB rosters on most teams, and they have a ridiculous amount of legit MLB starts: Beckett, Matsuzaka, Lester, Buchholz, Wakefield, Colon, eventually Schilling, plus youngesters like Pauley, Zink, etc, who would absolutely be first-option AAA types on any other team). They have some great young players, so very promising prospects throughout the minors, and a MLB roster filled with great, professional talent of guys who know how to win.
All that said, Pioli/BB have done the same thing: great depth, great flexibility, an eye to the future, and a constant winning culture; but they've done it in a capped league and for that I give them the edge.
As for Ainge, I'll give him credit for the trade...but that absolutely fell into his lap. He was rebuilding the team for a half a decade and wasted a number of peak seasons of Paul Pierce...the fact that he fleeced McHale doesn't shock me as McHale is one of the worst GM's in the sport. I think we can all admit it, even if we are big-time Celtics fans: the franchise got lucky as hell with that trade; if they win a title or two it'll all be worth it but in three seasons they'll be a terrible team once again, and Ainge doesn't (imo) have an eye toward the future like the other two.