At Middlesbrough I'd say it's Keith Lamb.
I think it's a bit harsh, he's done some excellent things for the club; Instrumental in signing Juninho, Robson, Gazza, Tuncay, Ravanelli, Viduka, Yakubu, Hasselbaink, Overlooked the upgrade to the youth academy, the move to the Riverside etc etc.
But he's also done some ridiculous things; Signing Alves against Southgate's wishes, offering Strachan the job when Southate was still in charge, offering Strachan the job, the Forlan affair, the Ziege affair, the numerous contracts he's failed to bother negotiating until other clubs come sniffing on the free and more.
On the fence.