5. Anderson – £22.05m
One of the few notably expensive mistakes on Sir Alex Ferguson’s transfer dossier, Anderson seemingly crumbed beneath the weight of his £22.05m transfer from FC Porto. The Brazilian seemingly lacked the drive to succeed at Manchester United and after eight seasons of constant lowlights and failing to convince supporters he was worthy of wearing the famous red shirt, he returned to his home country with Internacional in February 2015.
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