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Prison, Jeremy Kyle and how LFC transfer flop nearly joined Real Madrid

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They boast numerous winners’ medals in the World Cup, European Championships, Champions League, UEFA Cup, La Liga, Bundesliga, Ligue 1, Eredivisie, Super Lig, FA Cup, League Cup, Copa del Rey, Coppa Italia, DFB-Pokal, KNVB Cup, Turkish Cup, FIFA Club World Cup Championships winners’ medals and the Olympic Games.

On this day in 2007, Liverpool signed Jermaine Pennant from Birmingham City for a fee of £6m.

Here's the story of his Liverpool career: When looking back at the Liverpool side that faced AC Milan in the 2007 Champions League Final, you see a team that won 845 international caps between them.

Yet he very nearly joined Real Madrid instead.

Considering his talent, did Pennant fail football or did football fail him?

Between them they have lined up for the likes of European giants Real Madrid, Barcelona, Bayern Munich, AC Milan and AS Roma following their stints at Anfield.

The winger was never shy of controversy, but played well at times at Anfield before a fall out with manager Rafa Benitez and sale to Portsmouth.
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