Jermaine Pennant has recalled how he nearly signed for Real Madrid from Liverpool

Jermaine Pennant vs AC Milan

Jermaine Pennant is yet to officially hang up his boots, but there's no doubt he's reaching the end of his unusual career.

The 35-year-old's most recent spell saw him fail to make an impact at non-league outfit Billericay Town.

Off the pitch, he's been seen on Celebrity Big Brother and The Jeremy Kyle Show within the last few months.

Unfortunately, he has always seemed to embrace his reputation as a football bad boy, having earned the unwanted record of becoming the first Premier League star to play while wearing an electronic tag following his release from prison in 2005. 

From the point of view of most fans, and indeed most professionals within the game, those exploits have done him no favours.

There was a time, however, when he was much more highly-rated. As a youngster, Arsenal took him onto their books, but it's for his time at Liverpool that he's remembered best.

The English winger played in the 2007 Champions League final defeat to AC Milan and there was an argument to be had at his peak that he deserved a call-up to the national side.

Steve McClaren wasn't convinced. Yet, according to Pennant himself, he did attract enough attention to earn himself an unlikely move to Real Madrid - but it never materialised.

Why Pennant's move fell through 

"Real Madrid wanted to sign me when Juande Ramos was in charge there. The board wanted to do the deal as they wanted a right-winger," he told the December issue of FourFourTwo.

"On transfer deadline day I got a call from my agent, saying, 'You could be going to Madrid – keep your phone on'.

Pennant played in the Champions League final in 2007

"But the board had gone over the manager's head, so he started to get upset, and to placate him they pulled the plug on the deal. The club wanted me; the manager didn't."

When he looks back on the various ups and downs of his career, Pennant must wonder if things might have been different if he had clinched a move to the Bernabeu.

It's true that at the time, in January 2009, Los Blancos were looking for a winger.

Marca claim that Ramos, who was appointed just months after being sacked by rock-bottom Tottenham having earned just two points from their opening eight games, spoke to Spurs' former sporting director Damien Comolli about who was available.

Ramos was not happy that the board had gone over his head

The newspaper have it that Wigan's Antonio Valencia was Ramos' first choice, but Real eventually plumped for Julien Faubert, a player Comolli had seen at West Ham.

Nobody will ever know if Pennant would have been a greater success than Faubert, but he can't have fared much worse. 

Do you think Pennant wasted his talent? Have your say in the comments. 

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