Steve Cotterill has confirmed Matt Ritchie's Pompey career is over.
The Blues midfielder is expected to complete a move to Swindon in the coming days.
And fellow homegrown talent Marlon Pack also looks to be on his way out of Fratton Park.
Cotterill has made it clear he doesn't see either player making their mark at Pompey.
Ritchie is expected to command a small fee for his move to the County Ground, with his deal up at the end of the season.
Fans had hoped to see the Gosport talent succeed at the Blues, with similar hopes for Buckland lad Pack.
Boss Cotterill has had time to make his assessments since taking charge at Pompey in June – and it's bad news for both men.
He said: 'Matt Ritchie's move to Swindon will become permanent in January.
'I've been down to see these lads and tried to picture whether they would be good enough to play in the Championship. The answer to that is "no".
'I've seen them enough. I've seen Matt at Swindon and seen Marlon Pack at Cheltenham in that environment and the answer is "no".
'They may as well get on with their lives. One of them will definitely become permanent and the other one may become permanent.
'There is a fee involved for Matt.
'It might be possible to invest it back in the squad. Hopefully it will be but we will have to have a look at it.
'We'll have to see what I can do with it, whether it's for wages or transfer fees because that's the big issue.
'It's not going to be massive, so it won't be a big reinvestment. We won't suddenly take the Championship by storm on it.
'Matt wants to go there and he's playing football. There is no problem with that.'
Cotterill may well call on Tom Kilbey for the trip to Watford this evening.
But of the youngsters he took on the club's pre-season tour of America, the Pompey boss sees Joel Ward and Nadir Ciftci as the only players with futures at Fratton.
Cotterill said: 'They are not good enough. These are nice lads we're talking about here but they are nowhere near playing in the Championship.
'Perry Ryan is out on loan to Bognor Regis. Billy Goddard is out for the season – he did his cruciate.
'Pete Gregory and Ellis Martin are not going to play. We made that clear from the off. They have been playing for the under-18s as over-age players.
'I'm not trying to be clever but they are not going to play. If I've got three subs, they will not get on.
'Tom has just come into it probably through default. Tom is a great lad – a really nice kid.
'But certain players have been put in situations that they shouldn't have been. In the end, it doesn't do any of them any good.
'That's why it's good for the young players to be out on loan.'