“How Am I Sitting in a Cell Like I’m Some Murderer?” – Jermaine Pennant Opens Up on Prison, His Vodka-Fuelled Arsenal Hat-Trick & Facing ‘Puppy’ Lionel Messi

From Partying Before His Arsenal Debut to Facing Messi in La Liga – Pennant’s Honest Reflections on a Turbulent Career

Jermaine Pennant has always been one of English football’s most unpredictable characters — blessed with pace, flair and confidence, but haunted by chaos off the pitch. Now 42, the former Arsenal and Liverpool winger has opened up about the dizzying highs and devastating lows of his career in a raw and emotional interview on The Beast Mode On Podcast with Adebayo Akinfenwa.

From serving time in prison, to scoring a Premier League hat-trick after a night out drinking vodka, to facing a young Lionel Messi in Spain, Pennant’s stories paint the picture of a man who lived fast, fell hard, and somehow managed to keep getting back up.

“That’s It, I’m Done” – The Shock of Being Sent to Prison

Back in 2005, Pennant’s world came crashing down. Then on loan at Birmingham City from Arsenal, he was sentenced to three months in prison for driving offences — a moment he describes as the lowest point of his life.

“The worst thing I could’ve dreamt of happened,” Pennant recalled. “I thought: ‘That’s it, I’m done, my career’s finished.’ I was in a state of shock. When the guards came to take me, I was thinking, ‘Has this really happened? What am I going to do? Am I going to get beat up?’”

Pennant served 30 days in a Category A prison — a facility reserved for the most serious offenders. For a young footballer who had once been billed as one of England’s brightest talents, the experience was terrifying and surreal.

“I had a single cell. I think I cried on the fourth day in,” he admitted. “The first two or three days were just shock — I was numb. Then it hit me. I broke down. I kept asking myself: What have I done with my life? I was playing for Arsenal, setting up Emile Heskey, celebrating with fans, and now I’m in a cell surrounded by people convicted of murder and terrorism.”

The routine inside prison was brutal, but Pennant found small moments of relief in physical activity. “They let me go to the gym twice a day — that was my escape. I’d join in the football games too, but it was madness,” he said with a laugh. “It was like Mean Machine with Vinnie Jones. I had to jump over tackles just to stay alive!”

Those 30 days, though short, changed his outlook forever. “I’ll never take freedom for granted again,” Pennant said. “I wrote letters to my family, to my partner, even to fans. It makes you think about everyone you’ve hurt.”

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Sign Me Up – I Don’t Care About Wages!” – Getting a Second Chance

Amid the despair, a lifeline arrived. While still behind bars, Pennant received news that Birmingham City wanted to sign him permanently once he was released.

“My manager called me and said Birmingham were over the moon with my loan move — they wanted me permanently. I didn’t even ask about wages. I said, ‘They could pay me in KP nuts and a couple of cans of Coke, I don’t care. Sign me up!’”

It was the break he desperately needed. Birmingham’s faith helped him rebuild his career, and Pennant would go on to feature for several major clubs, including Liverpool, where he played in the 2007 Champions League final.

The Night Before His Arsenal Hat-Trick – “I Got Home at 5am”

Pennant’s story isn’t just about redemption — it’s also about the wild, impulsive side that made him both entertaining and exasperating to managers. One of his most infamous tales comes from the night before his full Premier League debut for Arsenal.

Arsenal had paid £2 million to sign a 15-year-old Pennant from Notts County — a record fee for a trainee. Years later, still fighting for a regular first-team place, he found himself invited to an FHM party at the Emporium nightclub in London.

“Ashley Cole was going, Paolo Vernazza was going — all the boys. I had FOMO,” he laughed. “I tried to talk myself out of it — told them I’d leave by midnight. They said, ‘No way, if someone sees you out, you’re finished.’ They left, and I thought, ‘Sod it.’ Got a cab, turned up 10 minutes later. They ignored me for 45 minutes to teach me a lesson!”

One drink led to another. “I ended up getting a bit Lionel Messi,” Pennant joked, using his own slang for being drunk. “Got home at 4 or 5am, probably slept around 6. Then I had to meet the team at 11:30 at the Four Seasons Hotel. I felt like death.”

He wasn’t expecting to start — until Arsène Wenger revealed the lineup.

“Arsène pulled back the sheet and I saw my name on the right wing. I just thought, ‘Oh no, that’s me.’ I was sh*tting it. I could still taste vodka.”

His plan? Fake an injury.

“I told myself, ‘Just pretend your hamstring’s gone after 25 minutes.’ Then I scored one. Then another. At half-time I thought, ‘Maybe go off now.’ Then I got my hat-trick. I was like, ‘Forget that, I’m playing 90 minutes!’”

Pennant’s hangover hat-trick against Southampton remains one of the Premier League’s most bizarre origin stories — a wild moment that summed up the chaos and charisma of his career.

“Look at Him” – Facing the ‘Puppy’ Lionel Messi

After leaving England, Pennant had a brief but unforgettable spell in Spain with Real Zaragoza in 2009–10. It was there he encountered a young Lionel Messi — a meeting that left him both awestruck and humbled.

“We played Barcelona and actually went 1-0 up,” Pennant recalled. “We were buzzing — for about five minutes. Then Messi comes out and goes, ‘None of that on my watch.’ He definitely scored two, maybe a hat-trick, and we lost 4-2.”

After the game, Pennant went to speak with Thierry Henry, his former Arsenal teammate who was then at Barça.

“I was chatting to Thierry in the doorway, and he nods towards Messi and says, ‘Look at him.’ Messi was sitting there like a little infant — he looked like he should’ve been in kindergarten! Thierry just looked at me and went, ‘Jermaine (gestures with his hand)… that’s him.’ Coming from Thierry, that said it all.”

The experience stuck with him. “I walked off the pitch thinking, How’s this puppy doing this to us? I felt violated,” he said, laughing. “We lost 6-1 once — I barely touched the ball. My manager took me off before the hour and patted my back like, ‘There’s nothing you could’ve done.’”

Life After Football – Lessons Learned the Hard Way

Today, Pennant speaks openly about his mistakes, his regrets, and his moments of madness. He admits his off-field lifestyle often overshadowed his talent, but he’s found a way to turn those experiences into lessons for others.

“When you’re young, earning money, and surrounded by people telling you you’re the best, you think it’ll never end,” he said. “But it does. And when it does, you realise all the people you thought cared about you, they’re gone.”

Pennant has since appeared as a pundit, motivational speaker, and podcast guest, often reflecting on the mental health struggles that followed his turbulent playing days. “Prison taught me about perspective,” he says. “You can lose everything in a second. But if you’ve still got people who believe in you, you can climb back.”

The Pennant Paradox

NLD: Arsenal v River Plate

Jermaine Pennant’s story is one of contradictions — a gifted winger who could destroy defenders one day and destroy his own career the next. He partied before games, wore an electronic tag during matches, and once outshone legends like Thierry Henry and Robert Pires on the same pitch.

Yet, beneath the bravado, there’s a clear sense of vulnerability. His recollections of prison, loneliness, and wasted potential reveal a man who has spent years coming to terms with who he was — and who he still wants to be.

“I’ve made mistakes, but I’m still here,” he said with a smile. “I’ve seen the top and I’ve hit rock bottom. But I wouldn’t change it, because it made me who I am.”

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“Beast Mode On” – Pennant’s Final Message

As Adebayo Akinfenwa wrapped up the Beast Mode On episode, Pennant left listeners with one final reflection — equal parts humility and humour.

“I’ve had some crazy times, bro,” he said, laughing. “But if my story helps even one person realise that you can mess up and still come back stronger — then it’s all worth it.”

From prison to Premier League glory, from vodka-fuelled hat-tricks to being mesmerised by a young Lionel Messi, Jermaine Pennant’s journey isn’t just a football story — it’s a reminder that talent alone isn’t enough.

It’s about learning, falling, and getting back up. Every. Single. Time.