Plenty of professional footballers have gone on to lose everything and go bankrupt after wrapping up their playing careers. But not too many have had the rollercoaster journey of Jermaine Pennant.
The former Arsenal, Liverpool and Birmingham City man was viewed as a ‘bad boy’ during his playing career, which never reached the heights expected. Pennant was a promising wide player in his younger days, but became a journeyman very quickly, not sticking around at any club for longer than a few years.
He looked destined to eventually earn an England cap when he was appearing in a Champions League final for Liverpool in 2007, but Pennant’s life decisions may have been behind his career being derailed. In early 2023, the retired winger’s life hit a real low point.
Ever since making a decent amount of money, the midfielder-turned-pundit has lived a luxurious lifestyle, including fast cars, expensive homes and lavish holidays. Pennant has admitted he is terrible with money and would’ve blown even more than the £10 million he actually did (per The Mirror):
“In all honesty, I could have been a billionaire and still f****d it up.
“I have made so many mistakes but I did not know how to deal with things and would not think of the consequences of my actions.”
He was officially declared bankrupt in January 2023 after racking up debts of around £1 million. He owed money to HMRC, banks, councils and utility companies.
The way he’d lived his life, spending money on anything and everything he wanted, Pennant had blown his entire fortune, which he estimates to be around £10 million. A divorce from his wife, Alice Goodwin, led to further losses, as everything mounted up.
Pennant revealed he was diagnosed with ADHD and PTSD from childhood trauma in 2024. His ADHD led to the ex-England youth international forgetting he owned a house that he originally bought for £1.2 million.
After moving from Liverpool to Real Zaragoza, Pennant was still paying the interest-only mortgage on the six-bedroom property in Cheshire. The mansion was left unoccupied when he was in Spain, but was later taken over by a drug gang, who caused a fire at the home.
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The winger failed to live up to expectations after his incredible Premier League debut.
Despite admitting to overindulging in the purchases and decisions he made, the now 43-year-old is adamant he doesn’t know why he was declared bankrupt. He told talkSPORT (per The Sun):
“The bankruptcy did not happen overnight. It came from years of bad decisions and ignoring things. We disputed the tax bill and I still do not know what it is for.
“But that is the thing that led to the bankruptcy more than anything else. I had no idea what I was earning and what was coming out of my account.”
Losing his career earnings isn’t the scariest experience in Pennant’s life. While playing for Birmingham City in 2005, Pennant was sentenced to 90 days in jail after admitting to drunk driving while disqualified after previously being banned.
He initially identified himself as his friend Ashley Cole when questioned, but eventually served 30 days before being released. Opening up on the harrowing experience in prison, Pennant admitted in a 2025 interview:
“The worst thing I could’ve dreamt of happened. I thought: ‘That’s it, I’m done, my career’s done’. I was in a state of shock. I was like: ‘This is not happening – is there a way I can appeal?’ I can remember the guards coming in, taking me into the van. Then the journey to the prison, I was like: ‘Has this really happened? What am I going to do? Am I going to get beat up?'”
Pennant admitted to being in ‘pure shock’ and disbelief that he had gone from being a Premier League footballer to sharing the prison with dangerous criminals.
“I think I cried the fourth day in. The first two or three days were pure shock. I was still numb. Once that went away, I broke down. What have I done with my life? How have I got here? I was playing for Arsenal, playing in the Premier League, setting up [Emile] Heskey for goals, celebrating with my fans, had the world at my feet at one stage.
“How am I sitting in a prison cell like I’m some terrorist, murderer, rapist, because that’s who I was amongst. I was in a Category A prison, which is for the worst offenders out there.”
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Former FIFA referee Mark Halsey has made an interesting comparison between Lionel Messi‘s foul against Algeria and Folarin Balogun’s red-card offence in the United States win over Bosnia and Herzegovina.
Balogun opened the scoring in the USA’s 2-0 win over Bosnia in the Round of 32 at the World Cup on Wednesday night. The former Arsenal striker then received his marching orders for a foul on Bosnian defender Tarik Muharemovic.
The pair battled for the ball, and Balogun’s studs made contact with Muharemovic’s calf. Brazilian referee Raphael Claus initially missed the incident before VAR intervened and sent him to the pitchside monitor, and he subsequently brandished a red card.
There has been widespread debate over Balogun’s sending off and USA boss Mauricio Pochettino hit out at the decision after the game. He said, It’s ‘never a red card’ because there was ‘never any intention to step on the player.”
Pochettino also weighed in on the comparisons between Balogun’s sending off and Messi’s foul in Argentina’s 3-0 win over Algeria, which didn’t lead to a red card: “For me, neither are red cards.”
Messi didn’t even receive a yellow card for a foul on Algerian defender Aissa Mandi in Argentina’s group stage win. The 2022 World Cup winner scored a hat-trick in that game, but some argue he deserved the same punishment as Balogun, given the similarities between the two incidents.
Halsey defended the decision to send Balogun off because the replays show his studs make contact, even if accidentally. He did, however, opine that Messi’s challenge on Mandi was “far worse” while speaking to The Sun Football on X:
“If we go back to Argentina vs Algeria, a challenge by Messi. That challenge by Messi on Mandi, he had no chance of playing the ball; it’s a poor challenge. He rakes his studs down the back of the Algerian player’s calf.”
He added: “For me, that was far worse than the one we saw with Balogun, which VAR should have recommended a review because it was a clear and obvious error by the match official.”
Balogun will now miss the USA’s Round of 16 clash with Belgium on Tuesday (July 7th) through suspension. He may even have his ban extended if FIFA’s disciplinary panel believe the challenge on Muharemovic warrants more than the one-match ban.
Fans were quick to recall Messi’s challenge in the aftermath of Balogun’s red card, and some feel the Argentina captain had been handed preferential treatment. A side-by-side replay of both incidents shows significant similarities, raising questions about FIFA officiating and inconsistencies.
Some viewers agree with Halsey and feel Messi’s challenge looked even worse than that of the American frontman, who had been enjoying a superb campaign. One fan wrote on X: “Messi went unpunished for his. He didn’t even get a yellow card. Balogun did even less than Messi and still got a red card.”
British broadcaster Piers Morgan made his feelings known on social media, posting images of the two fouls. He captioned it: “Same tackle. One (Balogun) gets a red card. The other gets no punishment at all. Must be nice being Lionel Messi.”
Some fans have gone as far as to suggest “corruption” and “favouritism” shown towards Messi. The eight-time Ballon d’Or winner will be in action for the reigning world champions when they face Cape Verde in the Round of 32 on Friday night.
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