13. Khalid Boulahrouz
Khalid Boulahrouz was a versatile defender who could fill in for Mourinho at several positions. The problem was that Boulahrouz was not good enough to start ahead of others who were in that Chelsea team. Mourinho decided to move on from Boulahrouz after a single season, and he loaned the player out for the 2007-08 campaign. Boulahrouz never again played for Chelsea, and he has not since started for a club as massive as Chelsea. While the reported transfer fee of £9.24 million is not a crazy amount of money in the current landscape, it is still a lot to spend on a flop.
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