Jermaine Pennant’s career, from playing in the Champions League final with Liverpool in 2007 to appearing on Jeremy Kyle, is examined.
On this day in 2007, Liverpool paid £6 million to sign Jermaine Pennant from Birmingham City. The winger was never afraid of controversy, but he played well at Anfield until falling out with boss Rafa Benitez and being sent to Portsmouth. Here’s his Liverpool career timeline…
When you look back at the Liverpool team that faced AC Milan in the 2007 Champions League final, you see a team that combined for 845 international caps. They have won various medals, including the World Cup, European Championships, and Champions League, as well as the Olympic Games, UEFA Cup, FIFA Club World Cup, European Super Cup, and Intertoto Cup.
Meanwhile, they have won league titles in Spain, Germany, France, the Netherlands, Turkey, Denmark, Cyprus, Argentina, and Brazil, as well as domestic cups in England, Spain, Italy, Germany, the Netherlands, Turkey, Denmark, and Cyprus, and have played for European giants Real Madrid, Barcelona, Bayern Munich, AC Milan, and AS Roma after their time at Anfield.
In Athens, though, it was the one player with no international caps, no major winners’ trophies, and no big-name club on his CV following his stint at Liverpool who shone the brightest. The one who wound up in Billericay Town instead of Barcelona. Jermaine Pennant was a childhood Red who aspired to play for his beloved Liverpool at Anfield.
While the rest of his teammates went on to have great careers throughout the continent, making the most of every last bit of talent at the highest level imaginable, the winger’s story remains a peculiar tale of unfulfilled potential. Or was he simply not good enough?
In reality, he was always Rafa Benitez’s second choice player. The Spaniard never truly wanted to play at Anfield. Pennant joined Liverpool as a £6.7 million signing from relegated Birmingham City in July 2006 as a replacement for Dani Alves after the Brazilian’s own move to Merseyside fell through. He had been incarcerated for just over a year.
Nonetheless, his 2006/07 season was perhaps the greatest of his career, despite falling just short of an England call-up. In Athens, the then-24-year-old should have been entering his peak, with his finest years ahead of him, as the third youngest member of Liverpool’s starting XI after Daniel Agger and Javier Mascherano.
Instead, the 2007 Champions League Final was the best it could get. The winger retired in 2018, leaving Pepe Reina as the sole current player from that night’s starting XI. Now 40,
Pennant was most recently in the news for reasons other than football, when he appeared on the Jeremy Kyle program to try to mend his marriage with wife Alice Goodwin following a contentious stay in the Celebrity Big Brother House in 2018. Two years later, the couple divorced.
Pennant did travel after his tenure at Anfield came to an end. A move to La Liga was made, although with Real Zaragoza rather than Real Madrid or Barcelona. He also played for Pune City and Tampines Rovers in India and Singapore. There were further permanent spells at Stoke City, Wigan Athletic, and Bury, and he was most recently on the books of non-league Billericay Town as his career waned.
Liverpool has signed 34 senior English players since the start of the inaugural Premier League season in 1992. Even if they arrive at Anfield uncapped, English players such as one-cap wonders Neil Ruddock and Dominic Solanke do not have to wait long for their first international cap.
Pennant, along with Julian Dicks, Andy Lonergan, Ben Davies, and Harvey Elliott, is one of only five players to have never played for the Three Lions. It would be surprising if the latter did not shift and cut that number again sooner rather than later, having previously stood at just two in 2019.
Arsenal signed the then-15-year-old bright kid after breaking through at Notts County for £2million in 1999, a record transfer cost for a trainee at the time. In his 2018 autobiography, ‘Mental: Bad Behaviour, Ugly Truths, and the Beautiful Game,’ he stated that he should have stayed at Meadow Lane.
The revelations do not stop there. In May 2003, he scored a hat-trick on his full Arsenal debut against Southampton. Despite this, he did so with a hangover from being out till the early hours the night before. That was not an isolated incident. His resume is filled with stories of womanizing and wild nights out.
Following his release from prison after being convicted of drink-driving in March 2005, he became the first Premier League player to wear an electronic tag in a game with Birmingham City. In his memoirs, he openly admits to driving under the influence on a frequent basis and then continuing to drive when disqualified.
Then there’s the famed story of his Porsche Turbo, complete with personalised number plate, being discovered abandoned at a Zaragoza railway station with five months’ worth of parking charges following his rush to return to England and make a deadline day deal to Stoke City.
Pennant’s life has not been easy, having been abandoned by his mother at the age of three and reared by a drug-dealing father who eventually became an addict and served time in prison. He had no touch with his mother for the following decade, until he had to track her down to ask her to sign a passport application so he could travel to Paris with England Schoolboys. At one point, a relative even told him she died of throat cancer.
It’s incredible that a player with such a track record spent a decade of his career under the tutelage of Arsene Wenger and Rafa Benitez. Conflicts with the Spaniard were unavoidable in the case of the latter, as everyone who knows anything about either knows.
It was a doomed romance from the start. Under Benitez, Pennant played some of his finest football of his career, culminating in that Champions League Final performance in 2007. Since leaving Anfield, he has been fairly public about his feelings for his old manager.
“On the pitch, often I can see what’s best,” he writes in his book. Finally, after the players pass the white line, you must trust them. But it was continual directions with Rafa. He could have transformed a player into an Xbox, dressed me up like RoboCop, and put an image of my face on it at times.
“I’m not a defensive midfielder,” he says. I’m not James Milner, who likes to keep things simple. I’m a flair player who likes to do my own thing. But his continuous commands severely limited my options. They prevented me from being free. He could never let me do what I wanted.
“It’s difficult when you have so many instructions.” You’ve prepared some directions and methods, but he’s still ranting at you. You’re suddenly perplexed. You have two sets of instructions in your head and are unsure what to do.
“It means that you suddenly mess up with a simple pass because your mind is scattered.” Rafa was a nightmare in that regard. I would become so frustrated with how monotonous and repetitive training was that I would lose it and yell, ‘For ***** sake, just give us a little of a five-a-side!’ As a player, all you want is a little fun to make training enjoyable and vibrant.
“But, with Rafa, training was so boring that you’d come in and want to slit your wrists!” The amount of time we’d spend in training doing nothing but shape and tactics!”
Perhaps his career might have turned out differently if he had listened to Benitez. But he wouldn’t be Pennant then. After falling out with the Spaniard, the winger spent the remainder of his Reds contract on loan at Portsmouth, who were relegated from the Premier League.
Despite this, he was on the verge of joining Real Madrid. A bid was accepted, only for Juande Ramos to replace him with West Ham United washout Julien Faubert. Pennant definitely had skill, having been evaluated by Wenger, Benitez, and football’s most famous club. It’s debatable why he didn’t accomplish more.
He should have accomplished more. He should have his own collection of winner’s medals. He should have represented England. His transfer to Liverpool should not have signalled the end of his career. He should not have made news for his appearance on the Jeremy Kyle show.
Did Pennant fail football, or did football fail him, given his talent? To play in a Champions League final for Liverpool is every boyhood Reds fan’s dream. His career is reminiscent of a modern Shakespearean tragedy. Jermaine Pennant, on the other hand, lived HIS dream. Perhaps it was enough.
