Unable to command a regular place at White Hart Lane, highly-rated central defender Guy Butters ironically earned his Spurs elsewhere.
And it was Pompey who were the beneficiaries of the then-England under-21 international’s self-confessed impatience, with the lure of first-team football – albeit at a lower level – too difficult to turn down.
A £325,000 deal was sealed in September 1990, although a six-year spell on the south coast began in testing circumstances for the future Fratton favourite.
Butters said: ‘I wanted to play first-team football.
‘In hindsight, maybe I should have stayed there (Spurs) an extra year and fought it out a little bit.
‘I had three years left on my contract and had been playing regularly in the first team.
‘But then they brought in another couple of players and I found myself out of the team.
‘I saw the writing on the wall and just thought I was better off out of there.
‘There were two ex-Tottenham players who had gone there (Pompey) – Gary Stevens and Shaun Murray – so I knew it was a decent club.
‘So when they came in for me, I couldn’t wait to get out of the door.’
Butters made his debut two days after signing for the Blues in a second-division clash with Plymouth.
Short of match practice, though, it proved a game too soon as he was substituted by boss Frank Burrows at half-time.
Butters said: ‘I had been out on loan and playing reserve-team football, which is very hit and miss, and I was a bit rusty.
‘I needed a bit of time to get fit and I knew I would be alright.
‘Sometimes you can get away with playing in a game and sometimes you can’t.’
Brought back into the side, the Fratton faithful soon began to appreciate a ball-playing defender who was equally strong in the air and on the ground.
Butters said: ‘When I started as a schoolboy at Tottenham I was a midfielder, before I switched to centre-half for a reserve-team game against Arsenal.
‘Paul Mariner played for them and I did quite well against him, so then it was decided that defence was my best position.
‘I could read a game and felt confident on the ball because of the fact I had previously played in a midfield role.
‘Once upon a time I even played as a left winger, believe it or not, because I was the only boy at my school who was left footed!’
In his second season at the club, Butters formed part of a new-look Blues backline under recently-appointed boss Jim Smith – alongside fellow youngsters Andy Awford and Kit Symons.
The campaign’s curtain-raiser ended in a creditable 1-1 draw at title-favourites Blackburn Rovers.
And the team went from stength to strength with Butters at the heart of the dogged defence.
Sadly, though, an untimely sickness bug meant he played no part in the culmination of Pompey’s epic FA Cup run, which ended in agonising semi-final replay shootout defeat to eventual winners Liverpool.
Butters said: ‘We had a good young squad but with the right mixture of experience.
‘Players like Chambo (Mark Chamberlain), Steve Wigley, John Beresford, Warren Neill and Guy Whittingham were the older heads.
‘Then Kit Symons, Andy Awford, Darryl Powell and Darren Anderton were a group of younger lads all champing at the bit to get in the team – with the older heads on hand to guide them and calm them down when it was needed.’
Butters featured in all three rounds leading up to the Blues’ Cup quarter-final clash with Nottingham Forest.
He said: ‘A day or two before the game I fell ill – I was physically sick.
‘I think I must have eaten something dodgy.
‘The boss then went from playing a four at the back to a three and I was left out.
‘That’s football, though, that’s the way it goes – that is what the manager gets paid for and it obviously paid off.
‘But just being a part of it around the squad and being involved in all the build-up for the semi-finals was fantastic.’
The next season (1992-93) saw Smith’s men come within a whisker of promotion to the newly-formed Premier League.
But with a win from the penultimate game of the season at Sunderland almost certain to secure Pompey’s promotion to the promised land, disaster struck.
With the scores goalless and 20 minutes on the clock, Butters – an integral and impressive part of a Blues defence which conceded just nine Fratton Park goals all term – handled on the line and was given an early bath.
Striker Paul Walsh followed as the visitors ended the fixture with nine men and on the wrong end of a 4-1 scoreline.
Worse was to come as Pompey lost out in the end-of-season play-offs.
Butters said: ‘Knightsy (Blues goalkeeper Alan Knight) came out and the lad had chested it and knocked it over his head.
‘It was just instinct from me really – it was a great save!
‘But if I had more time to think about it I wouldn’t have done it.
‘That maybe cost us promotion at the end of the day.
‘I can remember being in the bath and then Walshy joining me.’
Successive seasons (1993-94 and 1994-95) in the lower half of the second division followed – despite many assured individual displays from Butters – as the Blues failed to live up to their promotion-challenging feat.
The 1995-96 season, Butters’ last full campaign in a Pompey shirt then threw up a final-day survival battle, as Terry Fenwick’s men travelled to Huddersfield needing to win to stay in the division.
Butters said: ‘I remember that game and all of the build-up well.
‘Fred Dinenage came in to one of the rooms before the game and told us to “stuff them”, so that was good motivation from Fred!
‘On the day, Andy Booth – who played for them – went off quite early on, which was a relief because he was a handful.
‘And then Deon (Burton) popped up the winner.
‘It was like the Alamo in the last 20 minutes – I was just trying to head it, boot it and get the ball clear!
‘And then, when the final whistle went, all I remember is the Pompey fans running on and jumping on me, which was great.
‘There were good celebrations on the way home as well!’
Butters’ joy was short-lived, though, as he found himself out of the Blues’ starting line-up at the start of the 1996-97 season.
Gillingham pounced in October 1996, with future Pompey manager Tony Pulis paying £225,000 for the Fratton favourite.
Butters said: ‘There was interest in me from Gillingham and I had found myself out of the team.
‘It was a similar scenario to how I joined Pompey really.
‘I wanted to play and provide a bit of security for my family.
‘I was just a bit gutted that I didn’t get the chance to say a proper goodbye to all of the fans at Pompey because they were all really good to me.’
Having donned the star and crescent on 185 occasions and grabbed seven goals, Butters went on to enjoy a successful career with the Gills and Brighton also.
Now aged 45, he remains in football, proudly working for the Seagulls’ Albion in the Community programme.
GUY BUTTERS ON...
I broke into the first team at Tottenham at the age of 18-19, and played before my time for England’s under-21’s team.
I have good memories from the 1989 Toulon tournament and earned three caps at that level.
I was still only 20 when I moved to Portsmouth but by that time I found myself a bit out of the reckoning, as I had moved to a supposedly lower club.
I think if it was nowadays, though, I would have gone on to play for England’s senior team.
That’s not being big-headed but based on the way they give caps out to anyone who plays in the Premier League.
I played 30-odd top-flight games so I am sure I probably would have got one in a friendly or something!
It seems odd to me that somebody getting League Two’s manager of the month in February is out of a job in April.
I especially think that a club like Portsmouth is built from its foundations upwards and that if Andy was given a chance to do that over time then he would have been a massive success.
When I was at Pompey I moved down to Hampshire from London and I am still here.
I have stayed ever since – I love the place.
It’s changed my family - my mum and dad have moved down and my missus’ mum and dad have moved down as well.
My kids have grown up around here – it’s a different way of life and we all love it.