With Matt Ritchie already being shown the door in January, the Pompey manager has decided that Pack and Kilbey are also not a part of his long-term plans and that letting them go is the best thing for their respective futures.
So, was Paul Hart's tenure as youth development coach a waste of time? Is Steve Cotterill being too hasty in letting these young players go? And how huge is the task that Andy Awford has on his hands in developing players for the club?
If you look at some of the youngsters that Pompey have championed as being "ones for the future" in the past, then you can understand why the past regimes at this club have simply bought players from overseas rather than go down the homegrown route.
Names such as Danijel Subotic, Franck Songo'o, Gauthier Mahoto and Paris Cowan-Hall were all expected to make an impact when they arrived at Pompey but yet they've all disappeared into obscurity.
It was believed that Paul Hart was doing a good job with the youth prospects at the time and although there have been plenty who have disappeared off the radar, Joel Ward has become one of Pompey's best players, Marc Wilson and Asmir Begovic have been hailed as bargains by Stoke fans and Lennard Sowah looked promising before being sold for peanuts.
So, perhaps the rest of the local lads and the cheap overseas youth recruits just simply weren't good enough? From all the names the club have released, how many have gone on to make forge a career at a high level?
I've seen Cowan-Hall's name appear on Scunthorpe's bench a few times but that seems to be the pinnacle of the achievements of those who have been deemed not good enough by those in charge.
Has Steve Cotterill has actually done the right thing in letting Pack and Kilbey go?
I'll admit that I'd have liked to have seen them given a run in the first team but the fact is that in the manager's mind there is no time to risk blooding inexperienced youth into the team whilst he still believes there is a play-off place to play for.
However, it does seem that Cotterill may be a bit too hasty in letting these players go, especially as he has ran them down in the media in the past when they have never been given the opportunity to prove themselves.
So what does that mean for the likes of Perry Ryan, Pete Gregory, Ellis Martin and Billy Goddard whose futures are yet to be decided? I fear that unless they make a huge impact on the club's they're expected to be loaned to in the near future, then Cotterill will show them the door too.
In terms of future youth prospects, Andy Awford really has got a tough job on his hands. Portsmouth Academy are currently well adrift at the bottom of the Premier Academy League Group A (though I'm not sure how much you can read into that) and the competition for young players in this area is tough.
This is because Southampton's academy is far more attractive to any youngster who wants to make a name for themselves because they have a proven track record of youth players going on to great things.
Awford doesn't seem to have a great deal of quality to work with at the moment but it's going to take time to coach the youngsters into good players.
At least 17-year-old Sam Magri is making a name for himself. The Fratton born defender has helped the England U-17 team to the European Championships in Serbia this summer.
I'm hopeful that he will be given his chance to impress Steve Cotterill in the near future and that he won't be discarded like some of the other prospects that won't be seen in a Pompey shirt again.