Non-league Billericay Town is the latest staging post for the former Arsenal and Liverpool forward whose career has traversed lows such as being sent to prison to the high of playing in a Champions League final

“I’ve seen things I don’t think anyone else has seen in football,” Jermaine Pennant says on a late afternoon streaked with fading sunshine in Essex. We sit together on a small concrete bench behind an empty series of pitches which nurture the football dreams of boys at the West Ham Academy but, today, provides the training ground for Pennant’s unlikely new team. Billericay Town play in the Bostik Premier League, a regional division of semi-professional clubs which occupies the seventh tier of English football.

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Pennant has played for Arsenal and Liverpool, scored a hat-trick in his first full Premier League game and appeared in Champions League and FA Cup finals, but the 34-year-old has endured too many bruising experiences to think only of past glory. “I feel good here,” Pennant says. “It’s the next step and I’ve had a taste of everything football can throw at you … the highs, the lows, the in-betweens. I can bring everything I’ve learned to what I do here.”

Billericay is different to everything else – from the bleak Meadows estate in Nottingham where he lost his mum to cancer at the age of three, to becoming the most expensive teenage footballer in Britain when he was bought for £2m by Arsenal as a 15-year-old, to his dad being jailed for dealing crack and heroin, to Pennant himself ending up in prison, to facing Milan at the Olympic Stadium in Athens in the 2007 Champions League final, to playing for clubs in settings as diverse as Stoke, Singapore, India, Wigan and Bury.

‘Prison did change me. I’ve got to take credit for not letting it destroy me’

Pennant stresses that Billericay is not a last resort for an ageing footballer often accused of squandering his talent by people who have never met him. “There were so many options,” he says after enjoying Edinburgh during his month-long trial at Hibernian in June. “It was not only Hibs. I could have gone to Turkey, Cyprus, back to India, Indonesia. This was definitely not the only deal on offer. People wouldn’t bat an eyelid if I went to the top division in Turkey or Cyprus but this is about the big picture. When I had the offer from Glenn Tamplin [Billericay’s millionaire owner and now manager] I couldn’t turn it down. There could be opportunities here to prepare for coaching or management.”

Few people might imagine Pennant as a future football manager because, to many, he remains locked in an image that stems from his wayward days which culminated in him serving a third of his three-month jail sentence for a drink-driving offence in 2005. His ill-disciplined behaviour at Arsenal and on loan at Birmingham City was echoed by an unhappy spell in La Liga, at Real Zaragoza in 2009-10, when he was never picked again after being late for training three times in two weeks. Pennant’s private life, featuring relationships with various glamour models, was often splashed across the tabloids.

Facebook Twitter Pinterest Pennant, with his agent Sky Andrew, at Aylesbury magistrates court to be sentenced on charges of drink-driving in 2005. Pennant was jailed for three months. Photograph: Mike Finn-Kelcey/Reuters

He now thinks about football and life with much more clarity and depth. “Definitely. I’m taking everything more seriously because you can’t play forever. You’ve got to grow up. You’ve got to be a man and take care of business and your family. Obviously, I made many mistakes. But I was young and it was exciting. You have a lot of money at such a young age – as well as the responsibilities and pleasures. You’re in the public eye and I was just enjoying it and not realising I was also a role model. But I’m different now.”

His formative years were shaped by the death of his mother. “I was with my dad from the age of three. He moved on multiple times, with multiple women, always chopping and changing. I’m the oldest of four. It’s me, one brother and two sisters. They stayed with their mums. So it was just me and my dad and wherever he went, I went. I never had that mum figure and half of my problems came from that point. I also didn’t have a stable dad back then. There was a big gap in my early-to-mid-teens where I didn’t have either.”

In the midst of such confusion, in 1999, Arsenal signed him from Notts County and his manager, Sam Allardyce, railed against the London club’s “underhand” tactics. A brittle and precocious teenager might have been rescued – but Arsène Wenger’s patience ran out. Years later Pennant praises Wenger before detailing how his Arsenal career unravelled. “Of all the managers I played under, Arsène had the most influence. That’s where I learned my tricks of the trade – through Arsène.

“But he never quite gave me the opportunity. That was frustrating but Arsène is very strict and if your attitude is not right he won’t give you that chance. At the same time that was half the reason why my attitude wasn’t always right. I was spot-on for months. I was playing well for the reserves but it was like he’d lost faith in me. It seemed as if no matter what I did I wouldn’t get that chance. It was hard because we had a great team. The Invincibles. I was proud to train with that squad every day.

Facebook Twitter Pinterest Pennant scores his first goal for Arsenal before going on to complete a hat-trick in a 6-1 win over Southampton in May 2003, the first game of the Gunners’ record 49-match unbeaten league run. Photograph: Daily Mail/Rex/Shutterstock

“You remember that game where I scored the hat-trick for Arsenal? The 6-1 win against Southampton [in May 2003 when Pennant’s only goals for the club came during a dazzling 11-minute burst in the first half]? That was my first-ever [league] start for Arsenal, it was great.”

His hat-trick marked the first match in Arsenal’s famous 49-game unbeaten streak which would carry the Invincibles to the title the following season. Yet Pennant made only 12 appearances for Arsenal during the six years he was contracted to the club. “After the hat-trick I was on the bench the next game [a 4-0 win at Sunderland to finish the 2002-03 season]. I thought that was the start of it and I would just kick on at Arsenal. But it never happened and I got more and more frustrated and lost interest. I thought: ‘This is going nowhere.’”

That frustration contributed to the loss of his driving licence nine months later and, in January 2005, the accident that resulted in his prison term. “Yeah, I went off the rails,” Pennant says, remembering how he smashed his Mercedes into a lamp-post while over the limit and still banned from driving. “My family wasn’t around and, being so young, you make wrong decisions. The next thing I was in prison.”

He looks up and says: “Of course,” when I ask if he remembers his prison number. “MX7232. I don’t think I’ll ever forget it. Prison did change me. But not many people experience that and then play in a Champions League final. I’ve got to take some credit for not letting it destroy me.”

Rafael Benítez and Liverpool signed him on a four-year contract in July 2006. He recalls how being doubted by Wenger’s assistant, Pat Rice, spurred him on. “I definitely used it. He told my agent: ‘He’s not going to make it.’ I don’t know if he had it in for me or if my personality was a bit rich. He’s old school, Pat, but I always believed I’d make it. At Liverpool I said to my agent after scoring against Chelsea and playing in the Champions League final: ‘I wonder if Pat watched the game tonight?’”

Pennant laughs. “I saw Pat again when I played for Stoke against Arsenal a few times. It was kinda frosty between us at the Britannia. We won 3-1 and I scored and ran past the Arsenal fans to rub it in. That was a good moment. For Pat to say: ‘You’re not going to make it’ and then I play the Champions League final and score against his team was pretty sweet.”

Facebook Twitter Pinterest Pennant trudges off the Athens pitch, followed by Steven Gerrard, after Liverpool’s defeat to Milan in the 2007 Champions League final. Photograph: Tom Jenkins/The Guardian

Yet Pennant had not sustained his early success at Liverpool. “The first season I did well. Liverpool were also the team I supported as a boy. So it was great. The turning point with Rafa came when I got injured. I had a stress fracture in my shin and the next season, after surgery, I was out for three months. I rushed back and didn’t play well in my first game against Wigan because I was trying to nurse it. After that I struggled to get back in the team. I just want to play because then I give 110%. If I’m not playing I don’t. I now know that’s wrong.”

Pennant’s new managerial ambition is underpinned by a realisation of how lost he would feel without football. “Three years ago I would’ve said: ‘No chance – as soon as I’m finished playing that’s it.’ But as you get older you understand more. When you go through a long spell without a club you think: ‘Can I go on without football in my life? It’s all I know.’ You start thinking how much you’d miss the boys. You’d miss celebrating a goal or a win. At least as a coach you’re still part of that. It’s still a job and I need to earn a living. I also have a lot to offer after everything that’s happened.”

Could there be a future coaching role at Billericay? “I’m sure. If everything goes according to plan and we jump the leagues my experience and football IQ might be very useful.”

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Pennant will confront the inequities faced by any aspiring black coach or manager. “It’s a tough battle and it’s sad to see in this time. But Chris Hughton and Chris Powell are showing that the minority are as good as anyone else. Chris Hughton took Brighton into the Premier League. How many managers have done that? It’s great. Hopefully it will open the eyes of owners and prove the colour of your skin does not define how well your team will do.

“You’d think the lower the level the more doors will open. All you can do as is try your hardest and make sure your team wins. Being a black manager makes you a little more focused I guess. But I’m not there yet. At the moment I’m concentrating on playing at Billericay.”

When Tamplin and I talk, while Pennant changes in a dressing room including other ex-Premier League players in Jamie O’Hara and Paul Konchesky, the Billericay owner and manager reiterates that his star signing will be offered coaching opportunities. “I don’t judge anyone on their past,” Tamplin says. “We’ve all gone through dark days. You have to be in the devil’s pit to learn the truth about yourself. I was in that devil’s pit for four months [when Tamplin was seriously depressed before using his wealth to transform Billericay]. Jermaine’s also been through that pit but he’s great now. I’m a born-again Christian, a businessman and a good judge of character. I take on no big egos, no bad eggs.”

Facebook Twitter Pinterest Pennant in action for Billericay Town in a pre-season friendly against Leyton Orient. Photograph: TGSPhoto/Rex/Shutterstock

Tamplin is convinced that, despite losing their opening match of the season to Kingstonian on Saturday, Billericay will be promoted to the Football League within five years. Such ambition means the Essex club is derided by rival supporters – amid rumours Tamplin is paying £30,000 a week in wages. “It’s rubbish,” he says. “No-one is getting more than a thousand a week. Not even Jermaine. He made his debut in a friendly against West Ham and we had the biggest crowd in our history. 4,582. Jermaine scored a corker. Top bins. Beautiful.”

I have no regrets coming here. I’m 34, not 24. Not many players play at the highest level all their life

Pennant is more understated. “ I want to do really well for the team – but there’s pressure because I played at such a high level so everyone expects me to score a couple of goals every game and be amazing. But it feels like a normal dressing room. I’ve known Jamie, Paul and Kevin Foley [who played for Wolves in the Premier League] for years so that gelling was automatic. Same with the other lads. It doesn’t matter who is full-time or who has jobs. I think some of them work on building sites but on the pitch we’re a team. If you’re lazy they’ll give you a bollocking. I wouldn’t expect any less. We’re all equal.

“My family are just happy I’m playing football in this country. And everything is great with my dad now. Everything between us is how it should be between a father and a son. He’s in great nick and a labourer now after he turned his life around in Nottingham.”

Pennant shows me one of his many tattoos. He reads the words inked into his right arm: “Somewhere between faith and luck lies destiny.”

Destiny for Pennant, right now, appears to be in Billericay. “Yeah,” he says with a wry smile. “But I have no regrets coming here. I’m 34, not 24. Not many players play at the highest level all their life. So this is just another avenue of my football life. I’ve had so many ups and downs but this is a new path.”