Danny Cowley has the opportunity to initiate another Fratton Park clear-out next summer with the deals of all but eight of his permanent first-team squad expiring.
In the past, the Blues have lost consistent performers such as Enda Stevens, Christian Burgess and Nathan Thompson on free transfers at the end of their Fratton deals.
That was under previous chief executive Mark Catlin, with Cullen taking over the Pompey role in June.
Now Cullen is challenged with overseeing the contract situation of the current crop of Blues players.
He told The News: ‘In an ideal world, you wouldn’t have so many out of contract, but we do have a number of players where have options as well, so that brings the numbers down quite considerably.
‘We haven’t opened contract talks, not at all. You wouldn’t start to do that until later on.
‘They’ll be talking to agents – and one or two agents are asking the question – but we will do it when it is right.
‘I look at individual players. I don’t think it’s right to say “Right, we’ll do this player now” or that player. We will look at the overall plan, which players are going to be part of it, where we need to improve, where we need to add.
‘Some players will be quite happy to see things out to the summer, others want a clear identification.
‘Sometimes you have to be a bit honest if you get to January and there may not be a contract for the player at the end of the season.
‘It does help to have that discussion because it may enable the player himself to get sorted early looking forward.
‘Of course you always have that risk of losing players. They are always going to have options open to them.
‘Whether we talk to players now, or January, or leave it until the end of the season, each will have its own set of dynamics which you have to work through.’
In addition, the loans of Gavin Bazunu, Gassan Ahadme, George Hirst, Miguel Azeez and Mahlon Romeo are also up.
Cullen added: ‘You have three parties – the club, the player and his representative – and you must come to an agreement on whether you are signing a new player or whether you are renewing an existing contract.
‘There will be players out of contract at Pompey who will be really, really keen to extend – and naturally there will be players who want to explore their options.
‘You may also get players that are well in contract, but are attracting the interest of other football clubs.’
A message from the Editor, Mark Waldron
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