5. Juan Sebatian Veron
Matthew Ashton/EMPICS SportChelsea should have known from the very beginning that signing Juan Sebastian Veron would be a bad idea. Following the midfielder's disastrous tenure at Manchester United, the Blues thought they'd seen something their league rivals had missed when they paid the Red Devils £15 million for his services in 2003. But, predictably, Veron had just as miserable a stay at Stamford Bridge as he did Old Trafford, and made only seven appearances for the Blues after struggling with injury problems. Chelsea twice flogged him out on loan - to Inter Milan and Estudiantes - before finally giving up and selling him to the latter in 2007. Having seen at close quarters Veron so badly flounder in the Premier League at United, Chelsea should have known better than to extend his dire stay in England. The Argentinian was named by
The Times as one of the 50 worst transfers ever in Premiership history, and cost Chelsea and United £77 million between them for his dubious services.