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Jimmy Floyd Hasselbaink has criticized Crystal Palace's management of Marc Guehi's situation following the collapse of the center-back's proposed switch to Liverpool on Monday.
The Reds were willing to play the long game in their pursuit of Palace's prized defender during this summer's transfer window.
Liverpool was convinced that, with Guehi's Selhurst Park contract set to expire next summer, it could secure his signature late in the window for a reduced fee.
This strategy appeared to be bearing fruit when the Reds struck a £35 million ($47 million) deal for the Premier League star on deadline day.
The London club watched as Brighton's Julio Igor, who was on the verge of joining on loan, was targeted by West Ham, prompting a dramatic U-turn.
Eagles manager Oliver Glasner insisted that securing an adequate replacement was essential before the club would sanction Guehi's departure to the Reds.
Former Chelsea forward Floyd Hasselbaink has now taken aim at Palace's handling of Guehi's situation, with the 25-year-old now poised to depart as a free agent next summer.
"The thing is, it's been hanging above Crystal Palace for a long time," he told Sky Sports.
"This is not the first window that they've been speaking about Marc going, so why is the replacement not ready?
"Why is there not somebody there
That's bad business for a club like like like Crystal Palace
It's just bad business."
The failed deadline day move is problematic for both Liverpool and Palace.
Overseas clubs are allowed to negotiate a pre-contract agreement with Guehi from January, with Barcelona and Real Madrid both thought to be interested in the player.
Should this happen, Liverpool will miss out on its primary defensive target, while Palace will lose the player for nothing.
And if Guehi goes to Liverpool during the January transfer window, Palace is unlikely to receive another $47 million offer for the defender due to there being less than six months left on his contract.