Colangelo had a good reputation in Phoenix, but his tenure in Toronto has been abysmal. He's has thrown money around irresponsibly, despite being given several chances at the kind of cap flexibility necessary to build a good long-term foundation. Colangelo has had cap space in 2006 and 2009 and came away with T.J. Ford and Hedo Turkoglu. He traded many key assets for an overpaid and broken-down Jermaine O'Neal, then somehow made things worse by signing Turkoglu with the money he saved by eliminating his own mistake. He's given out long-term mid-level contracts to marginal players like Jarrett Jack, Jason Kapono and Amir Johnson. He's overpaid his own flawed players, giving Ford a big contract despite his injury issues, Calderon a bigger contract despite his defensive problems and Bargnani an even bigger contract despite not showing he was worth it consistently. In other words, he's the worst stereotype of the impatient GM, unwilling or unable to contain himself when he has some money in his pocket.
That was taken from a new post courtesy of SB Nation's own Mike Prada regarding Colangelo's ranking amongst the league's GM's.
BC comes in at number 27 on the list, and while that may seem harsh, it also seems a bit much considering the likes of David Kahn, Mike Dunleavy and Chris Wallace appear ahead of him.
Personally I'd have Colangelo around number 22 on this list although Prada makes a good point; of the usual "worst-in-class" GM's ahead of BC, at least they have shown some existence of a plan being in place.
And unfortunately as we've seen the past few seasons, perhaps FINALLY with the exception of this coming one, Colangelo has swung for the fences each off-season without much of a long-term strategy, and most of the time gone down swinging.