6: Paul Konchesky
Another disastrous buy by manager Roy Hodgson, with the former Fulham boss deciding to bring the left back with him from Craven Cottage to Anfield for a fee of £4m when he also made the move from the west London club to the Merseysiders in the summer of 2010.
However, the Englishman’s signing went on to signify all that was going wrong at the time at Anfield under Hodgson, with the full back lasting only a little longer with the Reds than the man who brought him to the club.
5: Mark Gonzalez
It all started so well for the Chile international when he came off the bench with just five minutes to go to score a vital winner for his new team in a Uefa Champions League qualifier against Maccabi Haifa.
However, that unfortunately represented the high point of the wide man’s stop-start career on Merseyside, and only a year later manager Rafa Benitez had offloaded him back to Spain, where he joined Real Betis.