As one of the country’s most exciting young talents, the dazzling left winger was pursued by Barcelona and attracted a bid from Monaco.
After rejecting a three-year deal to remain with Claudio Ranieri’s Chelsea Pitt then spurned the offer of a Manchester United trial under Sir Alex Ferguson.
Instead the 19-year-old chose Pompey to launch his first-team career in June 2001 – and 10 years later was a Wolverhampton postman playing part-time for AFC Telford.
Sadly Pitt’s Football League presence totalled four seasons, 99 games and nine goals. A talent unfulfilled.
‘I coach in Burton’s Academy and always try to impress on the boys how they must do their best and be professional. Don’t ever live with regrets,’ he told The News.
‘Let your future be decided by the footballing side of it, not anything else.
‘For the talent I possessed, I underachieved. That was down to myself, not doing the right things in my second season to sustain that career.
‘I was young and very naive when I was at Pompey, yet what happened impacted upon the rest of my career. Those kinds of labels remain, things stick to you in football, and, without doubt, it affected my career going forward. I had a reputation.
‘I could have gone to Bournemouth on loan at one point, but my own manager, Harry Redknapp, blocked it. He told them not to take me because of my attitude.
‘These days, educating people is one of my main roles as a coach. I’ve been through it myself, through the schoolboy programme, through the scholarship, into the first-team environment.
‘I understand what you can do to stay there – and, more importantly, what not to do.’
Having signed for Chelsea as a 13-year-old, Pitt was earmarked as an exciting first-team prospect alongside his youth-team skipper John Terry.
Aged a year below the future Stamford Bridge legend, Pitt’s other notable contemporaries included Carlton Cole, Mikael Forssell, Robert Huth, Leon Knight, Sam Parkin and Warren Cummings.
Indeed, at the age of 18, Pitt would become the most-sought after of them all, attracting international attention which was rebuffed without hesitation by Chelsea.
Eventually, Pitt was lured away – by Pompey.
Pitt added: ‘My agent, Sky Andrew, also looked after Sol Campbell, who was letting his Spurs contract run down.
‘Everyone was watching him, including Barcelona, who had sent delegates over. Sky advised them to also come and see me in action – while tipping me off they’d be in attendance.
‘They came to youth and reserve games and liked what they saw. They were slightly interested, although I don’t know how far it got, I was never offered the choice to go there.
‘Chelsea rebuffed everything at the time, with Monaco actually putting in a bid. Barcelona’s interest made the national papers, my mum still has the cuttings.
‘Chelsea really liked me. Towards the end of the 2000-01 campaign, I was training with Claudio Ranieri’s first-team and had received an official club letter asking me to attend their forthcoming pre-season tour to Tuscany, Italy.
‘I was even involved in a few match-day squads, although without getting on the bench.
‘The issue was, I felt ready. I’d been playing youth and reserve-team football since aged 15 – the next step was the first-team. Wherever that may be.
‘I was prepared to leave Chelsea as a free agent to achieve that and had a few clubs to choose from, including Pompey, Wolves and Leicester City. There was also the offer of a Manchester United trial, but what was the point? I’d be doing exactly the same thing as Chelsea.
‘At Pompey were people who knew me. Graham Rix had been Chelsea’s first-team manager, while his assistant, Jim Duffy, was previously my youth-team manager. They knew my game and had my best interests at heart, they could help me improve.
‘Looking back, maybe I should have been a bit more patient at Stamford Bridge, but that was my character, I just wanted to play in a first-team environment. I pushed to leave and turned down a three-year contract.
‘Chelsea didn’t take it well. I was the only person to quit at that stage, normally everyone jumped at the chance to sign deals.
‘To be fair, that did prompt them to change their mindset in terms of the youngsters, everybody got bumper new deals because I left. The boys were praising me afterwards!.
‘Chelsea didn’t think I was going to leave. We were in contract negotiations for 4-5 months, but I felt I deserved more than they were offering. Then they tabled a good deal just when I was signing for Pompey.
‘I had already told Pompey I was going to join. I wasn’t going back on my word.’
A tribunal ruled the Blues must pay the Premier League club £200,000 for the 19-year-old, who signed in June 2001.
With Rix himself having arrived as Fratton Park boss four months earlier, owner Milan Mandaric had sanctioned a summer of eye-catching recruitment.
Joining Pitt on the south coast were Robert Prosinecki, Peter Crouch, Mark Burchill, Dave Beasant, Alessandro Zamperini and Yoshi Kawaguchi. In addition, Neil Barrett followed Pitt from Chelsea’s youth set-up.
What unfolded was 41 appearances and three goals for the left-sided winger as the Blues finished 20th in the First Division, which would later be rebranded the Championship.
It was a solid maiden campaign for Pitt, who finished it as a 20-year-old with Harry Redknapp now his Fratton Park manager.
Yet, having netted in a final day 3-1 defeat at Manchester City in April 2002, he never again featured for the club.
‘I don’t think I was a fiery character back then, but I’ve never been afraid to stand up for myself,’ he said.
‘If I think something is wrong, I will say it. Maybe that didn’t hold me in good stead.
‘My second season was the first time in my life that I hadn’t been picked. It was unfamiliar to me – and I didn’t react as well as I should.
‘Nowadays I’d have dealt with it in a different way, yet, as a young player, I didn’t handle it well. Unfortunately, I earned a reputation.
‘Those things stick, that stigma is hard to shake off. People judge your character and, at the end of the 2003-04 season in which I left Pompey, I didn’t have many options. That’s how I ended up at Boston United.
‘I believe that behaviour affected my career. I was tarnished – and the label followed me everywhere I went, which is why I ended up going down the levels.
‘As a coach, I try to give boys advice about perception, attitude, trying your best every day, because you never know who’s watching.
‘I arrived at Pompey as a 19-year-old and told I’d be involved in the first-team, although I don’t think they envisioned me being involved quite that much in the first year. Needs must at the time, I suppose.
‘It was sold to me that I’d be playing part of a front three – but I ended up being left wing-back. I’d never even played there before. Pompey fans didn’t see the best of me.
‘At that age I was never going to be consistent, especially playing left wing-back, especially being my first season and the hectic schedule of the Championship. For 41 appearances, I felt I did okay.
‘Ahead of my second season, I was tackled from behind in a pre-season friendly against Havant & Waterlooville. I was meant to be going on loan to QPR, but now required an ankle operation which kept me out until November.
‘That was me finished at Pompey, basically. I got on the bench a few times afterwards, but never made another appearance.
‘There is a resilience and mental side you are expected to deal with, regardless of your age. Those who don’t, fall by the wayside or tumble down the pyramid.
‘During my first Pompey year, there were a few of us youngsters enjoying debut seasons, playing a lot. Then suddenly the likes of myself, Lewis Buxton and Neil Barrett didn’t have any matches.
‘We were isolated in a different changing room, training away from the first-team, out the back away from everybody else. It was tough and I didn’t react well.
‘We knew we didn’t have any first-team games coming up. We’d be back home at 1pm after training, we had nothing else to do, so sometimes we’d go out drinking.
‘I lived on my own in Port Solent for three years, my family were in London, there was nobody to advise me. My agent did try, but I was young. I wasn’t listening.
‘It was my fault. I blame myself more than anyone else. I regret how I conducted myself when not playing.’
After 23 months without a Pompey first-team game, Pitt departed Fratton Park in March 2004 for a short-term deal with Oxford United, once more reuniting with Rix, their manager.
Pitt dropped spent the following season with Steve Evans’ Boston United in Division Three, featuring regularly.
His last Football League appearance was May 2005 – at the age of 23.
The winger then spent five seasons with fellow Blue Square Premier side Cambridge United, where he racked up 165 appearances and 16 goals, on occasions turning down the chance to return to the Football League.
A loan spell at York would then establish the unwanted statistic of three consecutive Wembley play-off final defeats by May 2010, yet his career continued.
When a brief spell with Weymouth was curtailed by the club’s financial issues, in November 2011 Pitt became a Royal Mail postman at the age of 30, while continuing football part-time.
There were spells at AFC Telford, Chase Town and Stafford Rangers, yet his playing days fizzled out.
The former Chelsea man completed a degree in PE and youth sports coaching from Staffordshire University, taught at Codsall Community School in Staffordshire, and then signed up to the PFA’s Professional Player To Coach Scheme.
The outcome was finding employment at Burton Albion in December, when he was handed an 18-month contract overseeing the League One club’s under-18s and under-11 and 12 sides.
And he’s hoping his football story can be heard.
The 39-year-old added: ‘Let’s hope the young lads take it on board, but I have been that age. I remember people telling me and it was “Yeah, whatever”.
‘Some of them think it’s about footballing ability and it’s not, there are many more facets and aspects that go with it.
‘I’m happy with the career I had, but I could have done better. I’m not complaining, I played football for 15 years – and it was still at a good level.
‘A lot of people don’t get to do it, only a small percentage make it. So, for that, I am very, very grateful.’
A message from the Editor, Mark Waldron
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