For Alan Ball, it was a case of third-time lucky when Pompey rubber-stamped the signing of Warren Aspinall in August 1988 – but only after the sought-after striker had himself stuck the boot in elsewhere.
A club record fee of £315,000 was agreed for the 20-year-old after Aston Villa let their leading marksman go, following a moment of ill discipline.
The Blues, who had twice failed to acquire the services of Aspinall from previous clubs Wigan and Everton, were the benefactors as they sought an immediate return to top-flight football following a short one-season stay among English football’s elite.
A combination of circumstance, persistence and cold, hard cash led to a six-year partnership that brought its fair share of highs and lows both on and off the field of play.
Aspinall said: ‘I was joint-top goalscorer for Aston Villa as we were promoted back to division one – the Premier League as it is now.
‘I scored 15 goals that season (1987-88) but had also been suspended twice through bookings accumulated in the campaign.
‘Graham Taylor (Villa boss) pulled me to one side on our pre-season trip to Scotland and told me in no uncertain terms the club couldn’t afford to have me missing any games in the top flight.
‘We played St Mirren away in a friendly and this burly old Scotsman kept coming through the back of me in the first 25 minutes.
‘He then scythed me down again, so, after checking the referee and linesman weren’t looking, I stamped on the fella’s chest.
‘The problem was the other linesman was watching and promptly began waving his flag.
‘As the referee pulled me to one side I was hoping I’d escape with a warning but he gave me a red card and I thought that was me done for.
‘After the game, Taylor called a meeting at the back of the coach.
‘He said: “Warren you will never play for Aston Villa again”.
‘Pompey came in for me and I spoke to Alan Ball and had no hesitation in signing for a legend like that – the time was right.
‘When I was at Wigan and Everton he wanted me but I decided not to go because it was too far at that age.
‘I was still only 20, though, when I signed and it was a record fee.
‘Micky Quinn, who I knew from my Wigan days, was an influence on me to sign for Pompey but I have to say I didn’t need much more reason than Bally really, he was a true gentlemen and a legend as a player and a manager as well.
‘I came down here and I’m going to be honest and say that’s when my problems with gambling started.
‘There was a big culture – we used to do three things as football players at the time: drink, gamble and play golf.
‘I stayed in the Meon Valley Country Club hotel but I couldn’t be bothered to waste time walking around looking for a golf ball so I knocked that idea on the head!’
On the pitch, Aspinall made a bright start to his Blues career, linking up with former team-mate Quinn in attack and netting in each of his first five starts for the club.
But the season was ultimately a disappointing one as the Blues failed to return to the first division, finishing in 20th position with Ball replaced by John Gregory midway through the campaign.
Things didn’t get much better for Aspinall, who on the first day of the 1989-90 season suffered a broken ankle that limited him to just 10 appearances that term.
He said: ‘I went on a bit of a run at Pompey when I first joined.
‘But then I got injured at Watford in the first game of the next season.
‘A ball was played into me and I laid it off and turned quickly.
‘My stud stayed in the grass and I heard a crack.
‘I had a spiral fracture in my right ankle and that kept me out for longer than I anticipated.’
When Aspinall finally returned to regular action, prolific Guy Whittingham had taken his spot up front and new boss Frank Burrows converted the tenacious northerner into a midfield role where he played regularly alongside Martin Kuhl.
An early experience of the position against England star Paul Gascoigne in the FA Cup proved an eye opener, though.
Aspinall said: ‘Frank Burrows played me in midfield one game and I got man of the match on television (in a third-round tie against Barnet), so I carried on.
‘We played Spurs in the fifth round and he told me to man-mark Gascoigne.
‘We lost 2-1 and Gazza got both of them, so I don’t think I did a very good job on him!
‘But that was it, I was made into a midfielder, although the managers came and went too frequently for my liking.
‘We got trigger happy – it was Bally, John Gregory, Frank Burrows then Tony Barton before settling with Jim Smith, who was a good appointment.’
And it was under Smith that Aspinall scaled the greatest heights in his stay at PO4.
Twice introduced as a substitute as the Blues lost out to Liverpool over two epic FA Cup semi-final showdowns, the converted Blues midfielder was denied the opportunity to write himself into Fratton folklore.
He said: ‘I think if we had got past Liverpool we would have won the final because we would have played Sunderland who were in our league.
‘I always blame Andy Awford for giving away that free-kick in the 1-1 draw at Highbury.
‘He didn’t react to it hitting the post either, so that’s two things he did wrong!
‘I always wind-up Awfs when I tell him he cost me an FA Cup final appearance!
‘In the Villa Park replay, I was down for the fifth penalty – I was the glory hunter.
‘But we only hit the target once, through Kit Symons – Warren Neill, Kuhly and John Beresford missed.
‘And it seemed as though Knightsy (Blues goalkeeper Alan Knight) was playing opposites in the shootout!
‘Every time they struck a penalty he dived the other way!
‘It was a great team, though, and we had a big chance the following season to earn promotion to the Premier League but threw it away.
‘We played Sunderland away at the end of the season and had both Guy Butters and Walshy (Paul Walsh) sent off.
‘We ended up getting beaten 4-1 and missing out on promotion by two goals.’
With Aspinall reduced to the role of frustrated substitute in the 1993-94 season, though, his time at Fratton Park was up.
Five years, 170 appearances and 22 goals later, Aspinall was on his way west to south-coast neighbours Bournemouth.
He added: ‘I was sub most of that time having got a couple of hamstring injuries.
‘Jim then brought a few people in and I just wanted to play.’
Aspinall went on to enjoy a successful spell at Carlisle before continuing his career in the lower divisions with Brentford, Colchester and Brighton.
He ended his playing days at the age of 33 after being struck down by MRSA following an operation on a broken ankle.
Sadly, the gambling and drinking demons which reared their ugly head in ‘out-of-hand’ card schools on the Pompey team coach continued to plague Aspinall upon his retirement from the professional game.
In 2007, aged 40, he came close to killing himself after blowing £1m on gambling and booze – sitting on railway tracks near his Hedge End home and waiting for a train to take his troubles away.
Desperate Aspinall managed to jump out of the way at the last minute after pictures of his family flashed before his eyes.
He is now clean, determined to stay that way and enjoying life working at a Sainsbury’s distribution centre in Basingstoke, while scouting for former club Brighton.