5. Anderson (Porto to Manchester United £25m)
Sir Alex Ferguson gambled on the 20-year-old in 2007 and it proved to be one of the few misjudgements by the Scot as Anderson never made the grade at Old Trafford.
The midfielder, constantly accused of being overweight and unfit, made only 70 Premier League starts in seven years and only left United for good in February of this year.
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