Pompey have made their fair share of off-the-field faux pas in recent times – two administrations in three seasons and a winding-up order from HM Revenue and Customs over unpaid taxes testifies to that.
On-the-field, though, the decision to offload homegrown goalscorer Ray Crawford still ranks as one of the most ill-judged in the club’s proud – and thanks to the unflinching loyalty of its fans in the wake of financial mismanagment, ongoing – 116-year history.
Put simply, the man nicknamed ‘Jungle Boy’ should never have been allowed to leave his beloved Blues in the summer of 1958.
Having earned that particular moniker after spending his Army National Service in Malaya, southeast Asia, Crawford, who lived down Fratton Road – a stone’s throw from Fratton Park itself – penned professional forms in October 1956.
The 20-year-old would have to wait until his 21st birthday and the opening game of the 1957-58 season, though, to run out in front of his fellow fans against Burnley.
Playing alongside surviving members of the Blues’ back-to-back championship-winning 1948-49 and 1949-50 sides, Crawford impressed but ended his debut goalless – something he understood to mean a wasted game.
Four days later, though, the local boy came good against Tottenham Hotspur, netting twice in a thrilling 5-1 success for Eddie Lever’s side.
An instant fans’ favourite, Crawford experienced an early setback in his career, with a broken ankle keeping him out of action for three months, but he then recovered to end his debut season in professional football with nine goals from 19 appearances.
But with the Blues only avoiding relegation to the second division on goal difference, the decision was made to dispense with the services of manager Lever.
The departing boss’ final words on his way out of Fratton Park were clear: ‘Whatever you do, don’t sell Ray Crawford.’
Incredibly, though, successor Freddie Cox did just that three games into the new season.
Crawford had netted once in his two appearances to continue a goal-every-other-game strike ratio for the Blues but new man at the helm Cox didn’t like what he saw.
Ambitious second-division Ipswich Town profited from a baffling decision to offload the in-form hitman as Alf Ramsey landed a £6,000 bargain.
Crawford reflected: ‘Being a Pompey boy, I came through the ranks from the youth team to do my national service in Malaya and then come back and force myself into the first-team.
‘I remember my coach at Fratton Park at that time was the great Reg Flewin and he used to say to me: “Look, if you want a career in football and you’re playing as a forward, you must score goals.
“No matter what team you are playing for, you can go out there and be the best player on the field but in your position it counts for nothing unless you score goals.
‘And that’s what I used to do.
‘I used to shoot on occasion – anything in or around the box I wasn’t looking to pass or lay on for someone else,
‘I was pretty greedy and he instilled that into me!
‘I was fortunate, though, in as much as that I got into the first team and got a few goals but I also broke my ankle that season.
‘I only had 19 games in the first team and scored nine goals, which isn’t a bad return in today’s reckoning.
‘In those days they probably thought that was quite ordinary for a striker, though!
‘Then of course, Eddie Lever got the sack – the board moved Eddie on and Freddie Cox came in.
‘He didn’t like what he saw in me and he moved me on.
‘I was later told by Eddie: “I told them not to sell you and I was quite adamant about that.”
Pompey’s loss was most definitely Ipswich’s gain as Crawford – as he had been at Fratton Park – became an instant success at Portman Road.
In 1961, the hotshot became only the second player after Dixie Dean to top the goalscoring charts in the top two divisions of English football in successive seasons.
Crawford, who claimed back-to-back league titles in the process would go on to earn two England caps and score for his national side against Austria in a glorious spell with the Tractor Boys,
But the Portsmouth-born striker was left wondering what he might have achieved had he been kept on at his hometown club, who had been swiftly relegated from the top-flight the season he departed.
Cox, who was sacked with the Blues on their way to a second relegation in just three seasons, would forever be remembered as the man who didn’t rate the country’s leading marksman.
Ramsey, or ‘Sir Alf’ as he is now better known, would go on to lead England to World Cup glory in 1966 and clearly had other ideas.
Sadly, the pair had gone their separate ways by the time football’s greatest tournament came around on home soil.
Crawford was in a second prolific spell at the Tractor Boys having scored goals for West Midlands rivals Wolves and West Bromwich Albion.
Aged 30, the second-division striker accepted his international chance had come and gone as he continued to score goals at Portman Road, before ending a prolific career in South Africa playing for Durban City.
Home comforts soon came calling, though, and just over a decade after his quite baffling departure, Crawford was back at his beloved Pompey unearthing players for the future as youth-team coach in 1973.
It was a job he loved and thrived in with the discovery and retention of Blues record appearance maker Alan Knight among others.
Crawford laughed: ‘Knightsie always holds that against me now doesn’t he?
‘He said: “I might’ve played for England if it wasn’t for you!”
‘Ron Greenwood (future England boss) wanted to sign him and I talked to Jimmy Dickinson (Blues boss) and said: “No, don’t let him go Jim – if Ron wants to take him to West Ham he must be some player!”
‘They were only offering us a few thousand quid for him at the time.
‘But I had a great time with the youth team – Steve Foster had just been kicked out of Southampton so we got him at Fratton Park and Graham Roberts was another we had a phone call from.
‘We let him go because Jimmy didn’t fancy him – that boy would run through a brick wall for you.
‘He ended up playing for England.’
Crawford would go on to become Dickinson’s trusted assistant in 1978 but the Blues manager would not be able to lead his team to the heights he had discovered as a player and relegation to the fourth division confirmed that.
‘Jimmy Dick was a great player, and a lovely, lovely man but as a manager – no it didn’t work.’
Crawford, now enjoying his retirement, remains a passionate follower of his hometown club at the age of 78 and has recently worked as both a summariser on Express FM, as well as penning his own column in The News.