5. Andriy Shevchenko –
No list of failed transfers can be complete without mentioning Sheva’s name. High price tag, higher hopes, disappointing spell. Milan’s medical team had indeed done a great job in analyzing the years left in Sheva’s career and finally giving a go-ahead to the AC Milan board for his transfer to Chelsea. Chelsea however, were too adamant for him to look into the finer details. Big big waste of money.