Article body analysed
By GETHIN HICKS Published: 18: 46 AEST, 29 July 2025 | Updated: 18: 47 AEST, 29 July 2025 View comments Jermaine Pennant has revealed he could have joined Spanish giants Real Madrid after being frozen out by Rafa Benitez at Liverpool. The English winger, now 42, enjoyed a successful Premier League career before eventually hanging up his boots in early 2018. He captured the attention of football fans at a young age, with a 15-year-old Pennant signed for a then-record fee for a trainee when Arsenal forked out £2million to bring him in from Notts County. He went onto make 26 appearances for the Gunners before really making a name for himself at Birmingham City, joining the Blues following a successful loan in 2005. It was only a year later however when Merseyside giants Liverpool came calling, with Pennant making the move north in a deal worth up to £8million. And the fee paid by manager Rafa Benitez seemed justified, with the flying winger cementing himself in Liverpool's first eleven and playing a crucial part in their run to the 2007 Champions League final, in which he played a full 90 minutes. Former Liverpool winger Jermaine Pennant has revealed he could have joined Real Madrid in 2009 The Englishman, now 42, enjoyed three seasons in Merseyside, and featured in the 2007 Champions League final But a fallout with Rafa Benitez in his final season left Pennant out of the squad and free to move But after two seasons at Anfield, Pennant was frozen out and left 'training on Saturday afternoons' after a fallout with manager Rafa Benitez. He featured just three times in the early months of the season and was free to leave in January - which is when Real Madrid chiefs called his agent's phone. Shockingly, Pennant joined a short list of players to turn Los Blancos down, opting for a move to Portsmouth instead - a decision he admittedly regrets. 'This is a crazy one and many people can't believe this, but Real Madrid wanted me, ' he told Adventure Gamers. 'It was my last year at Liverpool, I wasn't going to sign a new contract, and things weren't really working out between Rafa Benitez and me. 'Madrid came in needing a right winger for their squad depth, so we had that conversation and it was exciting, but then I asked myself if I wanted to go there and sit on the bench for three years or do I want to go somewhere to be a first-team starter and kick-start my career again? 'It was exciting but I wasn't keen at the time. Would I go back and change my decision? I wish I could. ' Pennant's agent Sky Andrew also spoke about the decision to turn Madrid down during a recent appearance on talk SPORT. Los Blancos came calling for Pennant in the winter of 2009, but he turned down the move He instead opted for a move to Portsmouth, joining Peter Crouch and then manager Avram Grant Pennant later settled at Stoke City, making 89 appearances for the club during a three-year period 'Pennant was just one of those people, his dream was to go to Liverpool, and when he messed that up, there was nowhere else to go, ' he said. 'So I rang him and said, "Jermaine, Liverpool have agreed a fee for you to go Real Madrid. " 'The narrative I got from the club is that they were just looking for someone to sit on the bench as a backup. The more I said it to Jermaine, the more he said, "No, I'm not sitting on the bench. " 'He's a nightmare when he's not playing. In the end they signed someone from West Ham (Julian Flaubert), who didn't play a game in the second half of the season. 'If Jermaine had gone there and not played, it would have been a disaster. ' Pennant instead joined Peter Crouch at Portsmouth that winter transfer window, making 13 appearances for Pompy in the second half of the 2008/09 season. He later made a Spanish move to Real Zaragoza, before settling at Stoke City, appearing 89 times for the club during a three years period. After stints at Wolves, Pune City, Wigan Athletic, Tampines Rovers, Bury and Billericary Town, Pennant called time on his playing career in 2018.
Share what you think
No comments have so far been submitted. Why not be the first to send us your thoughts,
or debate this issue live on our message boards.
By posting your comment you agree to our house rules. Do you want to automatically post your Mail Online comments to your Facebook Timeline? Your comment will be posted to Mail Online as usual. Do you want to automatically post your Mail Online comments to your Facebook Timeline? Your comment will be posted to Mail Online as usual We will automatically post your comment and a link to the news story to your Facebook timeline at the same time it is posted on Mail Online. To do this we will link your Mail Online account with your Facebook account. We’ll ask you to confirm this for your first post to Facebook. You can choose on each post whether you would like it to be posted to Facebook. Your details from Facebook will be used to provide you with tailored content, marketing and ads in line with our Privacy Policy. Published by Associated Newspapers Ltd Part of the Daily Mail, The Mail on Sunday & Metro Media Group