Indeed, he regards the 1996 controversy as a powerful reminder of the dangers of announcing a signing before registering the paperwork.
Pompey’s chief executive is adamant no fresh Fratton Park arrivals will be unveiled before Friday’s launch of the summer transfer window.
Of course, talks and negotiations can take place in the meanwhile, while some fellow League One clubs have gone public on signings, despite relevant paperwork not permitted to be lodged.
And Cullen rolls out Crook’s aborted move from Norwich to rivals Ipswich in the summer of 1996 as a prime example behind his own reticence.
He told The News: ‘You cannot register any paperwork until the day the transfer window opens, which is a new dynamic in the EFL this year compared to previous years.
‘A deal is never a deal until it is registered with the Football League – and you cannot register those deals until the transfer window opens (on June 10).
‘As a Norwich fan, I’ll always remember Ian Crook signing for Ipswich in the summer of 1996, with them parading him as their new player.
‘However, they never got the deal done, they couldn’t register it – and then he had a change of heart.
‘Days later he returned to Norwich after Mike Walker came back to the club, so was never an Ipswich player.
‘You can have all the paperwork in the book, but it can't be dated until that particular point, so the contract is not really valid and has no legal standing until that date.
‘There may be deals already done, there may be papers in drawers, but I think if you disclose it then all you’re doing is alerting potential competitors to hijack your deals.
‘You wouldn’t want to. If you have a deal done at the table, all you would do is heighten the risk of that deal potentially not going through.
‘Some clubs have done it by announcing signings, but there’s not many.
‘It's never, ever done, there’s still something which could be upset. Until it’s registered, there’s nothing to say in terms of whether you have the deal done or not.’
While the paperwork for new signings cannot be registered until Friday, there are exceptions, according to Cullen.
He added: ‘The only ones you are able to potentially do are pre-contracts from abroad or Scotland.
‘You can’t do pre-contracts in English domestic football from club-to-club. Although if the player was unattached in the last transfer window, that’s possible.’
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