2. Andriy Shevchenko
For a few years during the early to mid 2000s, there was not a more dangerous, prolific striker in Europe than Shevchenko. He had become an AC Milan legend, scoring over 150 goals for the Serie A giants, and he had enjoyed a great spell alongside the aforementioned Rebrov at Dynamo Kiev before that. When Chelsea signed him for £30.8m in 2006, it looked like a superb buy. The Ukrainian may have been 30, but he looked at the absolute peak of his powers. It quickly became apparent that Shevchenko had lost an edge to his game, however, and he scored just four goals in 30 Premier League appearances in 2006/07. His pace had gone, and his confidence in front of goal appeared non-existent. The following season didn't go much better for the Ukraine legend, as he found the net on just eight occasions. He rejoined Milan on loan in 2008/09, but was nothing like his former self, and having played just once for Chelsea in 2009/10, following his return from Italy, Shevchenko was sold back to Dynamo Kiev. He was a wonderful footballer at his peak, but the Blues spent an enormous sum of money on him and got very little in return.