They have traded most 2nd round picks. Every year, they talk about wanting to buy a late 1st round pick but always say the asking price was too high (which I think is silly because Colangelo seems to get cash considerations in just about every deal).
I think what has hurt the most is that they have had to do a full rebuild, top to bottom, every time their top player has left. McGrady and Bosh
left as, more or less, free agents, and they got nothing in the Carter