10 Most Expensive Transfer Flops In Premier League History

5. Robbie Keane

In the summer of 2008, Liverpool manager Rafa Benitez was looking for someone to partner Fernando Torres in attack, as the Reds tried to mount a genuine Premier League title challenge. When he snapped up Keane from Spurs for £19m, it was seen as the dream move for both parties. The Republic of Ireland legend had been a boyhood Liverpool fanatic, and he expressed his delight at the move. "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," he said. That happiness didn't last long, however. He got off to a very poor start to life at Anfield, and it took him 11 games to register his first goal for the club, in a Champions League clash with PSV Eindhoven. He didn't score his first Premier League goal until November. It wasn't long before Benitez lost patience, playing Steven Gerrard alongside Torres in a more attacking role and dropping Keane. By the time January 2009 rolled around, he was sent straight back to Spurs. The former Inter Milan, Wolves and Coventry striker scored seven goals for Liverpool, in an incredibly short-lived, hugely forgettable spell there. What a waste of almost £20m.