Fame, fast cars and Tampines Rovers – Jermaine Pennant's wild ride around football

Fast cars, faster women, building an empire and single-handedly reviving a foreign league; by any measure, life continues to be an adventure for Jermaine Pennant, as FourFourTwo discovered…

As part of an in-depth interview with new Tampines Rovers signing Jermaine Pennant, one of the questions FourFourTwo posed was: what advice would he give to his 16-year-old self, if given the chance?

They told me the Tampines chairman is a massive Liverpool fan and was very keen for me to come. I just said ‘yes, why not'

“Stay away from women,” was his initial response, delivered with a hearty laugh, before going on to state he would advise the teenager to have a good attitude, be professional and work hard in training.

It was a refreshingly honest response from a footballer who knows he doesn’t have a huge amount of football left, and yes, one that probably should have achieved more given his natural talent.

Yet, while he does confess to having some regrets – and Pennant’s colourful past is well documented – he is also proud of his achievements.

Excelling in a Champions League final, being heralded at clubs the size of Liverpool and Arsenal, and continuing a career that is now into its 19th year is certainly nothing to scoff at.

Following FFT’s interview with Pennant, many people wanted to know what he was like. Almost without exception, the expectation was he would have come across as difficult or displayed a poor attitude.

That could not have been further from the truth.

Pennant looks at home in his new colours

Personable, patient, downright likable even, while still showing flashes of the larrikin that has been subdued over time, Pennant has undoubtedly matured, this interview falling just a few days after his 33rd birthday.

He is aware what is at stake in Singapore, a country so removed from the highs of Merseyside derbies and FA Cup finals.

I’ve only just turned 33. There are easily three years left playing in Singapore or Asia

There is a significant opportunity for Pennant in this Southeast Asian republic – if he can play his cards right.

“I’m not sure who contacted who first or how it happened, but I was told there was an opportunity to come to Singapore,” Pennant explains.

“They told me the Tampines chairman (Krishna Ramachandra) is a massive Liverpool fan and was very keen for me to come, are you interested? I just said ‘yes, why not’.

“Obviously coming here I knew it was more than just playing football. It was to help the league and bring more to Singapore football.

“It was a bigger opportunity than just signing for a club. Knowing all that information I thought it would be a good opportunity for myself as well.”

From the moment he was linked with firstly just a trial at Tampines, he became the face of the competition. Before he pulled on one of the Stags’ shirts, let alone signed a contract, he dominated headlines across this diminutive, football-loving country.

Making it official with Tampines

He has heard of the wild expectations that have accompanied his arrival.

“Everyone’s saying can I revive the S.League,” he says with another big grin, but he understands many of those floating that possibility actually mean it in all sincerity.

Football has undoubtedly fallen on hard times in Singapore.

It’s crazy how (the press) could turn it (leaving his car at the station) into something like that

There are the odd highs, such as the battling, unexpected 0-0 draw with Asian powers Japan in a World Cup qualifier last June, but for the most part Singaporeans tend to have a cynical attitude towards their progress and standing in the world game.

That permeates down into the local competition, which is often the recipient of more scorn, combined with an undercurrent of hope that it can be revived and recapture past glories.

That’s where Pennant can play a role. Before he has played a game of any significance, he has already been labelled the biggest signing in S.League history.

That is in some ways an indictment on the competition itself, considering the calibre of players that have graced pitches in nearby countries such as Australia and Thailand.

But it isn’t a tag Pennant is shying away from.

“It’s great,” he declares. “Any positive feedback is good; it’s good for morale and for your confidence.

“Now I know how Messi and Ronaldo feel! No, no, but it’s great to be acknowledged and appreciated. I’ve just got to repay that when I’m on the field and also off the field.”

Therein lies a key to why some were initially sceptical about Pennant’s ability to make an impact in Singapore. That off-field reputation remains a constant bedfellow, whether he likes it or not.

Read on to learn about Jermaine's battles with the law and the British press, plus his thoughts on Singapore