It was a win-win...the complaint against Angelo was "he can't draft well in the 1st round!"...then when he traded 2 1sts for Cutler, those same people said "What are they doing trading away 1st round picks?!". As we all know, the problem wasn't that Angelo parted with 2 1st round picks in a trade, the problem was the return for those picks was Jay Cutler.
Its interesting how nowadays teams are loath to give away a 1st round pick in a trade...much less two 1st round picks. I wonder if Cutler was the last NFL player ever traded for two 1st round picks...I remember Joey Galloway was traded to Dallas (!) for two 1st round picks, but I think that was prior to Cutler.