#3 Andriy Shevchencko (AC Milan to Chelsea)
Andriy Shevchenko was signed by Chelsea in the summer of 2006 from AC Milan. With the club-record signing in their bag, Chelsea sent out a message suggesting that they intended to dominate the English football landscape for years to come.
Though Chelsea have been around the higher echelons of English and European football, Shevchenko barely played a part in it. The 2004 Ballon d’Or winner endured a torrid time at Stamford Bridge. In 48 appearances for the Blues, he scored a dismal nine goals, a tally not befitting of a top-drawer striker.
The Ukranian enjoyed a frosty relationship with his manager, Jose Mourinho, and it threatened to spill onto the pitch many a time. When Shevchenko arrived on English shores, he looked a player who had lost a yard of pace and didn’t seem hungry enough. Though he was still as adept as any in the technical department, he just didn’t have the pace to be a success in the Premier League.
After a couple of seasons, he was loaned to AC Milan in 2008. By that time, both parties were happy to put an end to their association.
Chelsea have made a number of shrewd acquisitions in the Abramovic era but the signing of the Ukranian was well off the mark. Shevchencko’s signing will surely go down as one of Chelsea’s biggest transfer failures ever.
He gets into our list at No.3 for the limited impact he had despite costing a huge amount of money.