Seeing you've gone back further to signing more than 4 years ago, I'd say Gavin Hoyte the hopeless loanee from Arsenal. Now found his level at Dagenham.
Agree that Smith was utter tripe - the worst goalie I've seen.
Agree with you about CMS totally. Another incredible bit of business by Darragh MacAnthony, getting that kind of money for League 1 striker who'd had a modest return in his previous one and only Championship season for P'boro. As well as being a decent bloke, he gives his all on the pitch, which...
Best - Bridge (still had immense pace, near perfect in defence, brilliant in attack)
Worst - Obika (Why, and why still on Spurs's books at that age, as he seemed clueless. The only time everyone on NSC agreed about a player!)