When David Bentley joined Tottenham back in the summer of 2008 for a reported initial fee of £15m, the midfielder himself expressed a sense of excitement at what the club could hope to achieve.
He said: “We can do anything we want, anything we put our minds to. You’ve seen what Juande Ramos did last year; the fitness and level of play has risen and I want to be part of that, hopefully we’ll keep progressing and doing well. It’s all there for us – if we’re all up for it it’s quite possible.”
Such was the confidence in what Bentley could bring to the table, that they confirmed his contract would last for a remarkable six years. What perhaps made the move all the more shocking was the fact he had come through the youth system at Arsenal, something that the then 23-year-old dismissed would play a part.
He added: “That’s in the past, I grew up through the Arsenal youth team but it’s not a problem for me, all my heart is at Tottenham and all my passion will be tunnelled into doing well for Tottenham.”
But fast forward a few seasons later however, and it was pretty clear that this was a transfer disaster for Daniel Levy. He played a total of just 62 games for the club, and scored a measly two Premier League goals altogether – to hammer home the point, he cost £7.5m per goal in the top-flight. Not the kind of record you would expect from someone who cost a decent chunk of money at the time.
Getting knee surgery during the 2011/2012 campaign saw him miss 35 matches and a total of 178 days out of action, and it essentially symbolised how anonymous he was. His stand-out moment was no doubt his volley against Arsenal in the north London derby, but even that doesn’t detract from the fact he was a miserable signing both on the pitch and financially too.
What made matters even worse for Levy in particular was the fact Arsenal received a percentage of the deal to sign Bentley in the first place, thanks to the agreement they had made with Blackburn in 2006. All in all, Bentley’s Spurs career was a nightmare that the Lilywhites would rather forget.