BC set the franchise back by signing Fields and extending DeRozan. He gambled on the former in order to land Nash, and the latter will never live up to his contract. I don't think Colangelo uses advanced stats and only gave DeRozan his money based on obvious stats. These signings have cost the Raptors cap flexibility moving forward.
If things improve from here hopefully they get to where they were last year with a top 6-8 pick. Yeah they lose the pick to OKC but how many draft projects does one team need anyway, they've been in the lottery for so long and are still stuck. Only if the team looks obviously bad with no hope of progress that maybe next time upper management will really house clean and the Raps can tank next year for Wiggins. If the Raps get close to sniffing the playoffs, management may not clean house. What's worse, BC will think the team has a chance and they lose out on getting Wiggins and the cycle continues. I'd rather hold out for a superstar prospect instead of continuing to draft and not hit any stand-outs.