10 Most Expensive Spurs Transfer Flops

9. Alan Hutton (£9 Million)

When Spurs signed Alan Hutton - a man being chased by Manchester United at the time - it was deemed to be a shrewd acquisition. At £9 million, the most promising player in Scottish football - and Rangers' star man - was set to walk into Spurs' first team and make the right back position his own. Except signing someone who had only ever played in the Scottish league was always going to be risky. He proved to be a major flop and only made 39 league starts in three and a half seasons at the club €“ a spell that included a loan stint at Premier League rivals Sunderland. Hutton joined Aston VIlla permanently in 2011 in a deal believed to be worth around £3 million €“ one third of what Spurs paid for him. At Villa, he has been loaned out to Nottingham Forest in the Championship, Real Mallorca in Spain during their relegation season and Bolton Wanderers in the Championship, though he now appears to have finally cemented his place in their first team.
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