Former Liverpool and Arsenal star Jermaine Pennant tells FourFourTwo the most money he ever spent on a night out
Liverpool and Arsenal old boy Jermaine Pennant was well-known for his off-field antics – now he spills his most extravagant night on the town with FFT

Jermaine Pennant, formerly of Liverpool and Arsenal, has told FourFourTwo about the biggest night out of his life.
The ex-winger was famous for his social life – and while we've asked him about the biggest game of his career in the past and what it was like to star for Liverpool against AC Milan in the 2007 Champions League final, we wanted to know what the equivalent was off the pitch.
Infamously, Pennant abandoned a Porsche in Spain and forgot about the car at an airport – when we were asked if are there any other big purchases that we hadn't heard about, the former Liverpool and Arsenal winger laughed, saying, "They're all out there!"
"When you’re a little bit drunk, you don’t rationalise things – and I tell you, there have been a few trips to Vegas," Pennant said, speaking to FFT on behalf of Casino Gambler.
"One Vegas trip was one night, one table: it ended up being £30,000. I look back and think, ‘That was really worth it!’ That was a great night… and that was definitely my biggest tab."
Pennant was a high-flying Premier League wide-man in his peak, however, capable of changing games. Although he talks about his partying now with a smile on his face, FFT was keen to know what he was most proud of during his football career.
"When I look back," he says, "At my goal against Chelsea at Anfield against Petr Cech… and my performance in the Champions League final when I was there on the pitch with Gerrard, Seedorf, Kaka and Pirlo – my antics kind of overshadow them.
Get FourFourTwo Newsletter
The best features, fun and footballing quizzes, straight to your inbox every week.
"I was a good player, though!"
More Liverpool and Arsenal stories
Jurgen Klopp has opened up about the club’s decision to launch a mega-money bid for Caicedo – while he's also been adamant that Salah will remain despite Saudi Arabian interest. Plus, FourFourTwo look at the seven ways Liverpool will embrace the Europa League to eventually deliver in Dublin.
Mikel Arteta has revealed the strange marriage metaphor he's used to motivate Kai Havertz. The Basque boss used another bizarre analogy recently to explain his tactics against Manchester City.
The Arsenal manager has had to defend Havertz already this season, notably after the 2-2 draw against Fulham. Meanwhile, Brentford striker Ivan Toney has revealed he would be interested in a move to Arsenal in future.
Mark White has been at on FourFourTwo since joining in January 2020, first as a staff writer before becoming content editor in 2023. An encyclopedia of football shirts and boots knowledge – both past and present – Mark has also represented FFT at both FA Cup and League Cup finals (though didn't receive a winners' medal on either occasion) and has written pieces for the mag ranging on subjects from Bobby Robson's season at Barcelona to Robinho's career. He has written cover features for the mag on Mikel Arteta and Martin Odegaard, and is assisted by his cat, Rosie, who has interned for the brand since lockdown.

‘Pallister had a cracking voice, but Parker, Keane and Irwin were hating it. All of the other lads were shuffling to the back, so I took the pressure off them’: Lee Sharpe recalls recording Man United's No.1 single

‘He instantly popped into our ratings as one of the best U21 midfielders in Europe. The impressive thing is Slot has made him into more of a no.6' Inside Ryan Gravenberch's transformation at Liverpool