10 Most Expensive Spurs Transfer Flops

5. David Bentley (£15 Million)

Poor David Bentley. Every negative Spurs article ever written seems to include him. And with good reason! He was absolutely terrible at White Hart Lane. Truly awful. The winger cost £15 million from Blackburn Rovers, having starred for the Ewood Park outfit for several seasons prior to joining Spurs, and earned himself England caps and a reputation for being a dead ball specialist. However, his time at Spurs was marred by poor performances, bust-ups and a generally bad attitude and he was loaned out no less than four times to all manner of teams at home and abroad. He scored just twice in 42 league appearances - and even a spectacular volley against his former club (and Spurs' fierce local rivals) Arsenal wasn't enough to push him up the pecking order. He retired in 2013 after having been dumped by the club. You can't help but think him signing for Spurs was to get one over on them, due to his prior affiliation with the Gunners, given his terrible performances for the Lilywhites.
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I'm a Tottenham Hotspur fan who loves comics and comic book movies.