Pompey are banking on offloading Prince Boateng, Nadir Belhadj, John Utaka and David Nugent to keep hold of prized-asset Marc Wilson.
Andrew Andronikou is desperate to raise 15m through player sales this summer.
Yet the Blues are loath to lose Wilson, who sparkled despite the club's plummet into the Championship.
The 22-year-old is now one of Pompey's most bankable assets, with a clutch of clubs monitoring the 3m-rated Irishman.
But Andrnikou believes, selling off Boateng, Belhadj, Utaka and Nugent during the next fortnight could effectively ensure ex-trainee Wilson remains at Fratton Park.
The quartet are already attracting interest both at home and abroad.
Boateng is being chased by West Ham and clubs from Spain and Germany, while Qatar side Al-Sadd are preparing for a second go for Belhadj after having a 1.5m euro bid turned down.
Nugent is interesting Bolton, while clubs from France are looking at Utaka.
In addition, Tal Ben-Haim has already gone, a relegation-release clause paving the way for an imminent switch to West Ham and saving the Blues almost 3m a year.
For Andronikou, the race is now on to ensure others follow the Israeli out of the exit door, meaning subsequent offers for Wilson can be resisted.
He said: 'We are looking to raise 15m at the minimum, so there will be players leaving.
'The values are there and the approaches are there. I just want to make sure someone like Marc Wilson does not have to go.
'We believe if we can sell Boateng, Belhadj, Nugent and Utaka we can raise that money.
'Marc is someone we want to keep, definitely, and is a player who will do very well in the Championship next season.
'It's fair to say I don't think the others will be able to adapt at playing at such a level and neither do they want to try.
'It is in all of our interests to sell them as soon as we can.
'The figures add up. If we can get 5m each for Boateng, left, and Belhadj, 3.5 to 4m for Utaka and 2m for Nugent that will give us the funds we are looking for.
'We wouldn't then have to sell Marc. We could keep him as part of the spine of the side next season.
'It's almost like a balancing act.'
Pompey are looking to sell Boateng, Belhadj and Utaka, in particular, before the World Cup finals – with all three involved in South Africa.
Boateng booked his place after being announced in Ghana's final 23, alongside one-time Pompey team-mate Quincy Owusu-Abeyie.
Andronikou is also hopeful Nugent can be moved on, with his former Burnley manager Owen Coyle closing in on taking him to Bolton.
He added: 'We are hoping to speak to David's agent over the next two weeks to find out what his client wants to do.
'I am told he is trying to stay in the Premier League and Bolton are interested.
'We are looking at 2.5m upwards – that would be a good fee.
'We are certainly not going to recoup what we have paid for him, while I would like to avoid paying his level of wages.'
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