Oliver Kay's Debate: pick your best - and worst - Manchester United team

Back in the days when he was known as inmate MX7232 at HMP Woodhill, serving a 31-day prison sentence for wrapping someone else’s Mercedes around a lamppost with a little too much alcohol in his bloodstream, it is easy to imagine that Jermaine Pennant aired the odd conspiracy theory among his fellow prisoners. Nothing too inflammatory, just passing observations, like the fact that an awful lot of the inmates — almost all — seemed to be English.

It always seems to be thus with Pennant. He is always the victim of some anti-English conspiracy. When asked upon joining Portsmouth on loan why he had become surplus to requirements at Liverpool, he answered by making dark references to Rafael Benítez’s perceived mistrust of “the English mentality” and observed, with a raised eyebrow, that “there are not a lot of English players” at Anfield — just as he did when he pitched up at Birmingham City four years earlier, saying that he would have made it at Arsenal had Arsène Wenger not shown such a disregard for homegrown talent.

There is a serious debate to be had about whether local youngsters get enough opportunities at those two clubs in particular — Liverpool’s reserve team against Middlesbrough last week featured 13 overseas players in the 16-man squad — but Pennant is an unconvincing standard-bearer for England’s lost generation.

When he talks of “the English mentality”, he does a disservice to those who are looking to make the most of their abilities while he appears content to keep squandering his.

It was ten years ago this month that Pennant, a week before his sixteenth birthday, left Notts County for Arsenal for a £2 million fee, a record for a trainee. He was hyped, inevitably, as English football’s next big thing, but those that he left behind at County cited two concerns about why he might not fulfil his potential.

The first was his upbringing in The Meadows, one of Nottingham’s toughest districts, where he lost his mother to cancer at an early age and was left in the care of a father, Gary, who was sentenced last month to four years in prison for selling drugs. It was not the ideal support network for a teenager fêted as the future of English football.

Depending on your viewpoint, that may or may not go some way towards explaining the second concern that was raised about Pennant back then. No sooner had the ink dried on that highly lucrative contract than his father was talking openly about the problems that Arsenal might encounter. “Jermaine was too comfortable at Notts and his attitude was sometimes wrong,” Pennant Sr said. “He thought he could get away with things like missing training sessions and turning up late. I think Arsenal will iron out the disciplinary problems.”

Wenger thought so, too, but it proved easier said than done. Stories soon emerged of a boy who would often turn up late for training — not drastically late, and always with an apologetic smile, but late enough to constitute a breach of discipline.

Pennant would take issue with those that called it a problem: “I might have turned up a little late for a good reason, but there wasn’t a discipline problem.” Wenger disagreed: “I would definitely call that a discipline problem.”

All Pennant had to do was to knuckle down. That is all that Wenger asked of him. It is all that David Platt asked of him when sending him home from the England Under-21 squad in April 2003 after he broke a curfew — by a matter of hours, not minutes. It is all that Benítez asked of him. Yet even in his mid-twenties, having had the short, sharp shock of a month in prison, having been given a second chance at a leading club when Liverpool came calling, punctuality remained a problem for Pennant.

There was a feature in Liverpool’s match programme called “the last word”, in which players would be asked a series of light-hearted questions: the last film they watched, the last meal they cooked and so on. When it came to “who is last to arrive for training”, Pennant and Charles Itandje, a goalkeeper who was born with his head in the clouds, were neck-and-neck. Their team-mates seemed to find it funny. Benítez did not. Eventually, Pennant and Itandje were put up for sale. Itandje, incidentally, is French.

Explore Football

• Premier League

• Football League

• Scotland

• European Football

• International Football

• TheGame

• Live Match Tracker

• The Fink Tank

• Fantasy Football