David Bentley
After shining for Blackburn Rovers, Tottenham Hotspur spent £15 million on David Bentley, with £2 million in add-ons, paying him £50,000 per week according to the Daily Mail.
The former England international was an unmitigated disaster for Spurs, and incredibly was contracted to the White Hart Lane outfit until 2013 – despite spending the latter years of his career on loan at Birmingham City, West Ham United and FC Rustov.
It was quite the fall from grace.
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