I'd say Whitehurst. It's not the actual trade for him, as we were taking a chance on a QB. We just over paid for him when we could've gotten him for cheaper.
Carpenter isn't a big deal to me, as you can move most Tackles inside to play Guard and get something from the deal. Robert Gallery was a high 1st round pick as a Tackle, but ended up making the Pro bowl at Guard.
Okung doesn't bother me as he's got all the tools and the attitude. He was also never injury prone in college, so it's impossible to call all his injuries. He's not living up to his draft cost, but that's not the FO's fault. They got the player they wanted, he just can't stay on the field
I honestly don't understand why people think Flynn is that bad of a deal. We didn't really pay him much more than a quality backup, and having him in our pocket actually got us Bobby Wagner. If we didn't have Flynn, Schneider probably would've drafted him in the 2nd, but we already figured we had our starting QB (or at the least we had Tarvaris Jackson who's a .500 QB on this team) so we were able to get Wagner and Wilson. I also still think Flynn would've been better than Jackson. You honestly can't blame him for being bad in Oakland: they had the worst OL in the NFL, no skill position help, and they got rid of Flynn be cause he had a bad start and the crowd boo'ed him. Seriously, what FO drops a guy because he got boo'ed ??
Sims and Vickerson both bother me slightly as we got rid of them for almost nothing and they've both had good careers. In Sim's case, better than most of the Guards we've trotted through in his absence. Getting rid of a guy is one thing, but not being able to find guys to replace him at that level means you messed up a bit. I'm not sure I blame the FO as that was most likely a Cable decision because he didn't fit the system (or was that Solari?).