#5 Andriy Shevchenko
Shevchenko's transfer fee of £30.8 million was a club record as well as a national record at the time. On paper, it was also the perfect signing as in his 7-years long stint at Milan he was arguably the best all-round striker in the world.
He started his Chelsea career on a bright note, scoring in the first game itself. That was as good as it got for the Ukranian for the rest of his Chelsea career.
After that, he could only score 14 goals in 51 games which was a very disappointing return by his lofty standards. He was mostly anonymous for Chelsea and it was annoying to see him completely fail to adjust to the pace of the Premier League.
He was soon loaned off to Milan and in the subsequent season got sold to Kiev. Though, pairing him with the footballing beast called Drogba was something that many fans or analysts could not understand. Both of them were players of similar style.