10 Most Expensive Transfer Flops In Liverpool History

3. Robbie Keane

In 2008, Benitez was looking to bolster his starting XI, and the Spaniard felt that bringing Robbie Keane in from Spurs would be a potential masterstroke. As it turned out, the Republic of Ireland proved to be one of the worst value-for-money signings in the history of Liverpool Football Club. He cost the club £19m. Having claimed upon arriving at Anfield, "I've been a Liverpool fan all my life, going back to when I was a kid growing up in Dublin, and I always had a Liverpool shirt on my back. So, to be here now as a Liverpool player is incredible and I couldn't be happier", there were many who felt it could be a match made in heaven, and that Keane had the ability to become a star at Anfield. From day one, however, he just never looked the same player who had been so brilliant at White Hart Lane. It took the striker 11 games to score his first goal for the club, in a Champions League clash with PSV Eindhoven at Anfield, and he didn't score his first Premier League goal until November, in a home game against West Brom. Having scored just seven goals in 28 appearances he was sent back to Spurs on loan in January 2009, roughly six months after joining the Reds. It surely has to be about the least productive £19m ever spent.