I liked the JO trade at the time it was made. As Claudius mentioned the S&T was a really good move. Instead of getting one player and losing all depth, Colangelo managed to turn nearly nothing at that time (although Humps has improved of late) into A. Wright and eventually Marco Belinelli.
The Kapono signing was terrible. A lot of fans disagreed at the time and were right. Instead of getting Pietrius, who mutually wanted to be a Raptor, we went with Kapono. That season could have turned out very differently if Bryan just went with the popular decision.