5. Fabio Coentrao
Mourinho likely hoped that he had landed a man who could start as a fullback or a winger when he signed Fabio Coentrao. What Mourinho instead got was a player who was nearly sold to Tottenham Hotspur two years after he joined Real Madrid. Coentrao became surplus to requirements, in part because of injury woes, after Mourinho left Real, and the player has been loaned out. While there is still time for Coentrao to make an impact for the Spanish giants, it instead appears more likely that he will be a regrettable signing made by Mourinho.
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