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#3 Jermaine Pennant
A classic tale of missed potential, Jermaine Pennant first came to prominence when he moved from Notts County to Arsenal in 1999 for a fee of £2m – a record for a trainee.
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Despite being considered one of the best prospects in England at the time, Pennant struggled massively with the Gunners and was quickly given a series of loan moves, during one of which (at Birmingham City) he received a prison sentence for a drink-driving charge.
After a move to Liverpool largely failed too, Pennant made a surprising move to La Liga club Real Zaragoza in the summer of 2009, signing a three-year deal with the club. Unfortunately, the move didn’t exactly go as planned.
The winger did make a total of 25 league appearances in Spain, but failed to score a goal and had his attitude brought into question on numerous occasions. After being frozen out for these issues, he ended up moving back to England with Stoke in the summer of 2010.
Pennant’s legacy in Spain was not a positive one by any means; his time there is probably best remembered for an infamous incident that saw his Porsche Turbo discovered parked in a Zaragoza railway station, covered in parking tickets – five months after he’d left the club. Supposedly, Pennant had forgotten that he owned the car!
