Spurs Transfers: 10 Most Wildly Over-Priced Signings Ever

2. Alan Hutton (£9 Million)

Signing anyone who has only ever played in the Scottish Premier League and expecting them to immediately be able to play in the English Premier League is a risk. Spending £9 million on them is madness. But that's exactly what Spurs did with a then-23 year old Alan Hutton in 2008. The Scotland international right back was brought in alongside Brazilian international left back - and fellow flop - Gilberto, as Spurs looked to make wholesale changes in their weak full back positions. However, at least Gilberto arrived for next to nothing. The £9 million Spurs spent on Hutton would prove to be a hugely over-inflated fee for a player who turned out not to be cut out for Premier League football. He made 39 league starts in three and a half seasons at the club - a spell that included a loan stint at Sunderland. He joined Aston VIlla permanently in 2011 in a deal thought to be worth £3 million - one third of what Spurs paid for him - and he has yet to cement a place at Villa Park. 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.