David Connolly has revealed two clubs have sought his opinion on a potential swoop for Jed Wallace.
Privately, the Blues are not hopeful Wallace will pen a fresh deal, having so far turned down two tabled offers.
Talks continued yesterday at the club with his representatives.
There have been enquiries to Pompey over the 19-year-old, but the fear is he could leave next summer as a free agent.
With Wallace being under 24, however, Pompey are entitled to an FA tribunal-set fee which, it is understood, could be around £200,000-£250,000.
Wallace has continued to impress on the field but Connolly knows his team-mate is being courted.
He said: ‘I have had two clubs I know speak to me and they are now in talks with Portsmouth over Jed Wallace.
‘Both of those people I have known for about 15 years and both trust my opinion.
‘I don’t want Jed to leave but one thing you have to have is a contingency plan.
‘And if he is going to go then I would rather talk him up to people I know and then they can come and offer two or three times more money now than if he went in the summer.
‘Again, I say, I hope he stays. But if he’s not going to sign a contract, the club obviously have to look after their best interests – and there is no-one else in for him yet, apart from the people I have spoken to.
‘If it happens and they get a lot of money, then brilliant, and the player gets the move because I believe they are both good clubs.
‘I said in the summer he could be like an Adam Lallana, and I want him to stay at the club.
‘But I don’t know if he will, so then you have to have a contingency plan otherwise you are stupid and run the risk, financially, of the club missing out.
‘I believe he has the right attitude and has a lot of opportunity to kick on and have a very good career.
‘It’s a great club, and in terms of which league we are in, I believe we will climb the leagues. It’s just whether Jed will stick it out for the time that may take.
‘Adam Lallana did but was financially rewarded for that.
‘I am not sure whether we are capable of doing that at this moment.’
Connolly is convinced Wallace has a bright future.
He added: ‘Jed has a lot of natural attributes as well as a willingness to run, and if you are a winger you have to be a hard worker in the modern game, absolutely.
‘There are lots of managers who say about players “how has he got rid of him?”
‘I’ll tell you why, out of possession he doesn’t work hard – but Jed out of possession works very hard and has the running power and physical capabilities to defend.’