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#7 Andriy Shevchenko (2006, €43.9 million)
Signed by Jose Mourinho for a then English record fee of €43 million, Andriy Shevchenko was one of the most feared strikers in the world at the time and was expected to take the Blues to new heights, as he was widely regarded as one of the best players in the world in his position.
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Shevchenko's stint in England, however, didn't go as planned as he struggled with injuries and inconsistencies during his time at the club. Mourinho offered him the #7 shirt and the striker arrived with superstar status, something he ultimately failed to live up to.
The Ukranian striker made just 48 appearances for the club and in the process, found the back of the net 9 times - a tally that neither paid dividends to his transfer fee, nor did his project his outrageous ability as a footballer.
Shevchenko returned to Milan on loan for the 2008-09 season but failed to get his career back on track, as he was sold to Dinamo Kyiv at the end of the season after just 2 goals in all competitions for the Rossoneri.
