Ray Crawford has expressed his surprise at the speculation over Conor Chaplin's future.
The striking legend believes Chaplin could thrive away from Fratton Park in years to come, if he’s sold.
But the former England and Blues front man is hopeful his first club will use the money from any sale to buy a powerful replacement.
Chaplin continues to be linked with a Pompey exit, with Coventry having a weekend bid for his services turned down.
Kenny Jackett is looking for more pace up front as he completes his summer recruitment, with Chaplin likely to make way after a relative lack of playing time.
It's not a move Crawford agrees with, however, and he feels the striker should have been given more minutes on the pitch.
A number of players have gone on to enjoy big success away from PO4 down the years.
Crawford feels Chaplin could well end up in that category, if he is sold.
He said: 'It's one I don't get.
'We're looking for a striker, but we've got a goalscorer here already.
'He hasn't played much football, so I don't blame the boy if he wants to go. But he should be given a chance.
'If the manager’s got a good, experienced player lined up that could make things look different, then good.
'If they want to get some money towards that it could work out.
'But when they said Conor could be going I didn't agree with it.
'I thought we should give him one more season here - and play him.
'They could be worried he's going to go for nothing.
'But what do you do? Get him in and boost him by saying you want to give him a new contract and play him? Or does he go?
'Through history we've brought through players and not got the best of them. I think this could be another one of them.
'You don't always know the insides of things and what's going on. But I'm surprised we're letting a goalscorer go. You don't know, he might go off and get as many goals as I did!'
If Chaplin is sold he will leave Pompey after making 121 first-team appearances since making his debut in 2014. But 85 of those appearances have come as a sub – a frustrating figure for the striker.
Crawford added: 'I've always admired him and I don't think he's been given a fair chance. There's been different managers and I wished he'd played more and been given some of the chances others have had.'
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