Many felt condemning Callum Johnson to a Fleetwood exile was harsh following an encouraging maiden season.
Then replacement Kieron Freeman was handed the opening six League One matches, before swiftly jettisoned in favour of perceived upgrade Mahlon Romeo.
If that wasn’t cutthroat enough, the Blues are now ready to listen to offers for the 30-year-old, who signed a two-year deal with a club option in July 2021.
Indeed, Freeman was a Cowley signing, his fifth to be precise, yet, within a year, the former Sheffield United man could be departing Fratton Park.
There may still be a future for Freeman, of course. For all the interest registered by admirers such as Hull, Mansfield and Swindon, he may still remain on the south coast.
Take Michael Jacobs, who appeared destined for Ipswich in one transfer window, then Doncaster in another, only to be handed a fresh Pompey deal earlier this month.
Nonetheless, Cowley has demonstrated his callous side during the hunt for the ideal Blues right-back.
All part of the cut and thrust of football, of course, as Pompey’s ambitious head coach strives to drag a club out of League One after five years of stagnation.
A promotion challenge in the forthcoming season is crucial, whether through the automatic route or play-offs, backed by a third transfer window few managers are fortunate to receive.
As a consequence, Cowley has tough calls to make and, in this instance, they have come at the expense of Johnson and Freeman.
Johnson remains a curious case, his departure greeted with much sympathy from supporters, many of which voted him as third choice in The News/Sports Mail Player of the Season for 2020-21.
Regardless, Cowley had sufficient time to assess the former Accrington man’s talents during the final 11 matches of the campaign following his arrival as interim head coach.
The following summer it was glaringly apparent newcomer Freeman was now ahead and, sure enough, Johnson was moved on loan to Fleetwood at the end of the August transfer window.
Not that Freeman had time to bask in the role – by mid-September his first-team opportunities also nosedived.
Those present at MK Dons will testify it was a visibly unhappy right-back who departed the pitch to be replaced by Millwall loan newcomer Romeo in the second half.
Freeman played just twice more in his favoured role, one of which brought the season-ending injury at Oxford United in February.
Still, with Romeo’s form dipping so frustratingly post-Christmas following chat of a move to Cardiff, Hayden Carter stepped up admirably.
Another loanee, the Blackburn youngster proved a class act, albeit purely as a temporary measure, like his rival Romeo.
This summer has seen Cowley release Johnson and is now prepared to offload Freeman as he bids to revamp his right-back options.
The head coach knows precisely what he wants from a Pompey right-back – and isn’t afraid to ditch those he feels are unable to reach such essential levels.
A message from the Editor, Mark Waldron
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