As a teenager, Courtney Pitt had the world at his feet.
An emerging star of an impressive Chelsea youth team, the Londoners were keen to hold on to a prized asset and in early 2001 offered the home-grown winger a three-year contract to stay at Stamford Bridge.
But with French champions AS Monaco’s £4million bid rebuffed and Spanish giants Barcelona circling, negotiations between club and increasingly-unsettled player broke down.
Unassured of regular first-team football at SW6 and unwilling to continue plying his trade at reserve-team level, Pitt then suffered an injury setback which put paid to growing interest from European football’s leading clubs.
As it was, first-division Pompey were the beneficiaries of Pitt’s decision not to put pen to paper with the Premier League heavyweights as a tribunal ordered the Blues pay their namesakes £200,000 for the services of the newly-found free agent.
Viewed as a major coup for the south-coast club, 19-year-old Pitt favoured a reunion with former youth-team coach Jim Duffy ahead of a swathe of other top-flight clubs, as Pompey boss and former Chelsea assistant Graham Rix raided the services of his old club thanks to his right-hand man’s connections.
Pitt said: ‘I was playing youth and reserve-team football at Chelsea and training with the first-team squad under Claudio Ranieri.
‘Barcelona and Monaco both wanted me and, at that time, I was flying in a very good youth-team alongside John Terry, Carlton Cole, Neil Barrett, Rob Wolleaston and Leon Knight.
‘But then I got a bad injury – I had a chipped bone in my knee and at the same time I suffered three stress fractures in my back.
‘That put me back a few months, so it took me a while to get fit again.
‘And obviously in football, things change quickly.
‘My contract was running out at Chelsea and I was offered a three-year deal by the club to stay but the opportunity to go and play regular first-team football was why I left.
‘I could have stayed and kept playing reserve-team games and then gone out on loan.
‘Who knows which decision would have been better?
‘But I don’t regret it.
‘Graham Rix had got the Portsmouth job and Jim Duffy, who was my youth-team manager at the time, became his assistant.
‘They enquired about me, so I chose to leave and go to Portsmouth to play first-team football.’
Things began well for both Pitt and a fellow new Blues recruit at PO4, with the decision to drop down a division in search of regular game time seemingly justified.
Towering 6ft7in striker Peter Crouch arrived at Fratton Park from relegated QPR, a foot taller than his teammate in waiting, and the little-and-large partnership got off to an impressive start to the 2001-02 season.
With Pitt ably supplying Crouch to five goals in seven games, the Blues rose to second spot in the early division one standings.
But a string of poor results, compounded by an embarrassing 4-1 home defeat to Leyton Orient in the FA Cup at the turn of the New Year convinced chairman Milan Mandaric to sack Rix in March 2002 – a year after his appointment.
Director of football Harry Redknapp took charge as the Blues fought off relegation fears, but by the season’s end, future England international Crouch had left the club for Aston Villa in a £5million deal and Pitt – although he didn’t know it yet – had played his last game for the club.
He reflected: ‘I signed on the same day as Crouchie.
‘We were very close, we both lived in Port Solent and used to be together all the time really.
‘I got him his move (to Villa)!
‘Me and Lee Bradbury always tell Crouchie we got him his move – we set up most of his goals.
‘We had a decent attacking side and started off flying that season.
‘Robert Prosinecki was a brilliant player – the best I have played with by far.
‘It was frightening what he could do with a ball.
‘And we had Mark Burchill, who got bad injuries which set us back badly, but I thought we did alright that first season.
‘There were lots of ups and downs but we had a lot of young boys in the team at the time.’
Pitt now looks back with mixed memories on his time at the Blues, which was cut short to 41 appearances and three goals.
The ‘tough’ Cup loss to Orient was followed by some better days.
Although Redknapp’s side ended the season with another defeat, Pitt’s final Pompey appearance was a far less painful occasion - not least because he entered the record books on a memorable day at Maine Road.
Manchester City celebrated winning the league title with a 3-1 success although it didn’t all go to plan for City.
‘That (Orient defeat) was tough.
‘We did alright in the first half and we were 1-0 up at half-time.
‘They scored an own goal when a defender turned my cross in.
‘But it was 1-1 early in the second half and then when we were pressing and trying to get a second goal, they hit us on a few counter-attacks and that was it.
‘We lost 4-1 which shocked everyone – that was a bad game.
‘We ended the season at Man City, which was the last-ever game at Maine Road – I scored the last away goal there.
‘I remember Stuart Pearce (City skipper) missed a penalty, though, for his 100th career goal.
‘Dave Beasant (Blues keeper) even said: “Put it in that corner and I’ll dive the other way” to get Pearce his goal but he put it wide!
‘That was my last game.’
An untimely injury on the eve of the 2002-03 campaign ensured that Pitt would play no part in the Blues’ glorious first division title-winning season.
By the time he was fit again at Christmas, impressive new signing Matty Taylor had nailed down the left-wing berth that Pitt had previously occupied.
The 20-year-old Londoner accepted he dealt with both the situation and uninterested boss Redknapp badly, but was always supportive of his team-mates and their achievements.
He reflected: ‘I got injured in a pre-season game against Havant and Waterlooville – someone did my ankle from behind and I was out until Christmas.
‘By that time we were about 10 points clear at the top of the league, so that was virtually the end of me really.
‘I was still in and about the squad and on the bench a few times but I never made another appearance.
‘Harry didn’t really speak to people who didn’t play, so it was a difficult time for me – I was young and I probably didn’t deal with it in the best of ways.
‘I had a bit of a go at him and a little sulk, but I learned from it.
‘I felt I had done alright in the games that I played but obviously in football, circumstances and managers change and people get injuries – in the end I knew I had to move on. But when we won the league I was delighted for the boys and especially for the fans.
‘We had a very good side and just to be in and around the camp when the boys were confident and flying was a great experience.’
With Pitt unable to fulfil his potential with the Blues, he was ironically loaned out to Luton – the club Taylor had joined from.
Further spells at Coventry, Oxford – reuniting permanently with former boss Rix in 2004 – and Boston followed in quick succession, before Pitt settled at Conference side Cambridge.
Five seasons and two failed play-off finals later, the winger was on the move again to York only to suffer further Conference play-off final agony, before leaving the professional ranks behind in 2010, aged 28.
Now 32, Pitt was most recently in action for Midland League premier-division outfit Tipton Town, where he is combining part-time football with scouting and coaching roles.
He explained: ‘I grew fed up of all the travelling, because I live in Wolverhampton, so going from Cambridge to Wolves and then Wolves to York was too much.
‘I still play local part-time football, though, and I’m doing a bit of scouting and coaching for a football agency.’