3. Jan Kromkamp
Now it is slightly debatable whether Jan Kronkamps signing was actually a bad bit of business. He moved from Villarreal in a swap deal which saw the hapless Josemi move the other way and what a relief that must have been for Reds fans. However Kromkamp was far from a success during his brief spell at Anfield. A staggering lack of pace was coupled with a complete inability to stop opposition crosses leading many to question the Dutchmans place in the side. It soon became clear that he wasnt up to scratch and Benitez moved him on to PSV. Not before he picked up his FA Cup winners medal after featuring on the bench in the final against West Ham mind. Well done Jan.