But he is adamant he will wait until the transfer window opens before delivering the career bombshells.
The Blues head coach is desperate to strengthen his squad and, in order to free up the playing budget, is prioritising the removal of unwanted members of his first-team squad.
Most susceptible are the 13 players out of contract at the season's end, among them a number of the club’s highest earners.
Cowley has made no secret of his wish to recruit a centre-forward and a central defender when the window reopens on January 1.
And he’s hoping to generate the finances by hastening the exits of those who won’t be handed fresh deals in the summer of 2022.
Cowley told The News: ‘We have to be creative, that’s the reality, trying to work as intelligently as we can.
‘We must find a strategy that allows us to get the very most out of our budget. To do that there are many different ways.
‘There are a number of players that will be out of contract in the summer – so if we’re not going to extend their contract I will be honest with them.
‘I will tell them, I will have an honest conversation, because I think that’s the right way to work.
‘Off the back of that, there might be one or two that will then want to accelerate the process and leave in the January window rather than the summer window.
‘I know it’s not healthy for me – or the player – to have that conversation now, considering there’s no action that either of us can make at this time.
‘I don’t think it’s the right thing to do in November. If I know on January 1, then I will have that conversation.
‘When the window does open, if I’m quite clear about their futures, then I will be honest with them.’
Of the 13 players out of contract in the summer, the Blues possess club options on Marcus Harness, John Marquis, Reeco Hackett, Michael Jacobs, Callum Johnson, Jay Mingi, Louis Thompson and Jayden Reid.
Others whose deals are set to expire are Ellis Harrison, Paul Downing, Sean Raggett, Lee Brown and Shaun Williams.
Cowley added: ‘There is also the possibility that clubs will come in and try to offer transfer fees for one or two of our players.
‘Every player at this level has a price, that’s just a fact, so there are two ways of being created.
‘There’s the possibility that one or two loans, if they are not playing regularly, will go back, which is another way of being creative.
‘Things will develop and unfold. The hardest thing in football is you must plan for every eventuality, which takes an incredible amount of time.
‘And things can change so quickly.’
A message from the Editor, Mark Waldron