Well as a bit of a codger I may try to intervene, we spent what was at the time relatively big money (about £250 000) on Frank McGarvey. During his time at Anfield he was capped twice by Scotland but never made a first team appearance, despite being very impressive in the reserves. Biggest difference probably was taht we got virtually our money back when we sold him.
For me the worst was Stewart, he was a big money signing, that i knew was shite before we signed him (and a Man U fan to boot) when we sold him we couldn't get anything for him. A couple of season later he was playing at Prescot Cables!
Shanks had a couple too- Jack Whitham, Alan Waddle anyone? John Wark was never the player for us that he was at Ipswich and went from being from being one of the most sought after players in Europe to a reserve team player in the space of fourteen months (mind u, he was top scorer in the year inbetween). Don't forget Babb was a record for a defender, and how much we laughed when Hysen fucked Man U off, and they had to go for Pallister instead! David Hodgson and Paul Walsh were both players i really rated before they arrived but never really reached the heights i expected, i'm not sure i ever expected taht of Diomede even as a world cup winner.
For disappointment the award would have to go to Collymore, enormous potential and a criminal waste, imagine what he thinks when he gets up of a morning now!
After all that look on the bright side, at least we never had Bernie Wright.............