10 Most Expensive Transfer Flops In Liverpool History

10. Andrea Dossena

When Rafa Benitez took Andrea Dossena to Liverpool from Udinese in the summer of 2008, it cost the club £7m. The Italian was seen as the Reds' new first-choice left-back, with John Arne Riise having left for Roma and Fabio Aurelio in and out of the team through injury. As it turned out, Dossena never got close to being a success at Anfield. Although his tough, no-nonsense style looked like it would adapt to life in the Premier League with ease, he often looked a little out of shape and unfit, and his performances were average at best. During a very disappointing first season on Merseyside, Dossena did at least enjoy a brief spell of personal glory. He scored the final goal in both the 4-0 home victory over Real Madrid and the 4-1 thrashing of Manchester United at Old Trafford, which came in the space of four days. Other than this rare high point, Dossena's time at Liverpool was a huge disappointment. He started just three games for the first-team in 2009/10, as it became more and more clear that Benitez didn't see him as part of his current, and future, plans. He moved to Napoli in the summer of 2010, but for a price significantly lower than what the Reds signed him for.