David Hay and nobody even comes close. Stephen Kenny and, to a lesser extent, Jimmy Mac had their moments but nobody has came close to that w**k. Took the best Dunfermline team in my lifetime and turned them to utter shite and was gone in less than a year.
Kenny is a bit of an odd one for me. Gave us that great Scottish cup run, wins over Hibs, Dundee Utd, Motherwell & St Mirren in the league were also highlights in 06/07, the motherwell one especially. Performance in the cup final itself was brilliant as well. Fine margins like De Vries dropping the freekick over the line up at caley thistle and Hamill not tracking his man/defence switching off for Doumbe's goal in the cup final cost him dear.
As for 07/08, the team that went down had rakes of talent (an astronomical combined wage I'll add too) which should have been enough to see us bounce straight back up. Think the first two games away at Accies and home to Morton showed that they weren't up for the fight. Kenny has been on record as saying that his instinct was to dismantle the aforementioned clique in the dressing room and start almost from scratch. Fine margins mate, fine margins.