#1 Fernando Torres (£50 million)
Well, we all know how this deal went for Chelsea now, don't we? This piece of transfer has been a major source of humour amongst their rival fans, including the Liverpool fans who were shattered to see Torres depart in 2011. Carlo Ancelotti had gambled by spending a club record fee of £50 million on the Spanish International who was already having his fair share of injury troubles after his brilliant debut campaign in England in the 2007-08 season.
Torres scored only one goal for Chelsea that season when he broke his worst goal drought. The Spaniard had played 903 minutes of football without scoring a single goal. And he did not trouble the opposition defences much in his Chelsea career which surprisingly lasted nearly four years!
Mocked, jeered and booed, Fernando Torres has an unfortunate record of 20 goals in 110 games in the Premier League for Chelsea. Thus, each of Torres's Premier League goal cost Chelsea £2.5 million!