Platform 1 at Southend Central station seems like an odd place to meet Steve Claridge. In fact, it is perfect: where better to talk to one of the greatest footballing journeymen than a train station? Claridge was there to offer his thoughts on Saturday's FA Cup Final. He favours Portsmouth, the town of his birth, one of the many teams he played for and one of the few he has managed.

Back in 1984, the club-hopper made his league debut for Bournemouth, closing the circle 23 years and 21 transfers later when he returned to make his final league appearance. His manager in 1984 was a certain Harry Redknapp, the man scheming Cardiff City's downfall. “He's still telling stories about me,” Claridge said. “I'm not sure how many are true.” Your best story about him? “I was on £25 a week and he tried to sell me a car for £50. I thought about it and didn't go for it. I came into training the next day and saw it getting loaded on a scrap van. I was wary of him after that.”

The second-best story isn't bad, either. “There was a record at the club for running round a circuit. I said I could beat it. He said, 'No you can't.' He bet me £100 and I knew I could do it. When we get to the day, I've turned up at the track and there are advertising boards on the inside lane. He says, 'Oh no, you can't move them.' So I've got to go round the things. And he's got a pacemaker in who did everything bar molest me.

“He was very gracious after the race. 'You're just out,' he said. 'You got so close, I'll let you off.' Twenty years later, when he could afford to pay me, he owned up that he'd let the stopwatch run on five seconds. So I'd managed to do it. His story is that I got out of the car on the motorway on the way home and ran the distance again down the A31. I certainly don't remember that.”

Claridge joined Portsmouth in 1998 and was player-manager for four months in 2000 before Milan Mandaric, the former chairman, deleted the latter part of his striker's job description.

“When I first went there, they went into administration,” he said. “Happened to me a lot, actually. It wasn't because of what I was getting paid. It's hard to imagine the club as it was and as it is now. The only thing that's stayed the same is the poxy ground. The first game I played, we got beat 3-0 at Oxford. Somehow we managed to stay up. And the club has basically gone from strength to strength.”

And Claridge went from club to club, making more than 1,000 appearances. Journey's end: Harrow Borough, last year. Why go on so long? “It's probably quite sad in a way. It's a tough game to give up. I look back now and realise how incredibly selfish I was. It's how you've got to be. I've only just started a family and I'm 42 years old. You give up an awful lot, but it's worth it.” For the sheer thrill of the goals? “How can I tell you what it is? You cannot explain that sort of experience. When you're trying to come to terms with not playing, soon you understand that there is absolutely nothing in life that can replace that.”

Not punditry, in which Claridge is a rare species, being insightful and frank? “It sustains, but it doesn't satisfy.” Hence a desire to return to management. After Portsmouth, there was Millwall, where he was ousted after 35 summer days, and Weymouth. But chairmen do not see deeper than the loveable rogue caricature, do not accept that he can roll up his sleeves as well as roll down his socks. “People talk about mistakes,” he said. “I made every mistake in the book.” And, indeed, in the bookmakers.

“But you grow up,” he said. “I've worked extremely hard to break down the perception of myself. I think in football, unfortunately, that is nine tenths of the law. I'm the type of person that actually goes home after one pint. But in others' stories, I've had 11 and find myself in a gutter.”

He won't stop hoping for another chance. For Claridge, like the commuters scurrying for the 17.40 to Fenchurch Street, it is just a case of finding the right platform.

Steve Claridge was speaking at a promotional event for National Express, official supporter of the FA Cup. National Express is running dedicated coach services to Wembley for Portsmouth and Cardiff fans.