Ranking The 30 Tottenham Transfers in the Daniel Levy Era

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#4 Worst Transfer: Darren Bent, Striker

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Transfer fee: £16.5 million
Former club: Charlton Athletic (Football League Championship)
Years with Spurs: July 1, 2007 — August 5, 2009
Stats: 79 appearances, 25 goals, 7 assists (in all competitions)

Few might include Darren Bent as one of Tottenham’s worst failures. He scored 25 goals over two seasons, right? That’s not good for a striker, but it’s also not terrible.

Considering that Bent ranks as one of the club’s most expensive transfers ever, his poor return rate wasn’t justified. Period. Levy and company were so disappointed in their investment that they sold him for a loss to Sunderland only two years into the Englishman’s contract. Bent promptly scored 24 goals in the next season for the Black Cats, damaging his reputation at Spurs all the more.

Next: Worst Transfer: #3