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In a ruling on Thursday, Mr Justice Fancourt said the apparent deletion of the dukeâs exchanges with John Moehringer on the Signal messaging platform, as well as drafts of Spare, before the bookâs publication was ânot transparently clearâ.
The judge ordered the dukeâs lawyers to carry out further searches of his laptop and examinations of his texts and Whatsapp and Signal messages from 2005 to January last year, for evidence potentially relevant to the litigation over allegations of unlawful information gathering.
He ordered Harry to make an interim payment of ÂŁ60,000 in legal costs to NGN after ruling largely in favour of the publisherâs bid for a wider search for evidence at a one-day hearing in London.
Harry, 39, alleges he was targeted by journalists and private investigators working for NGN, which also published the now-defunct News Of The World.
He is among a number of people to bring cases against the publisher, with a full trial of some cases due to be held in January.
The publisher has previously denied unlawful activity took place at The Sun.
Mr Justice Fancourt said there was evidence that âa large number of potentially relevant documentsâ and âconfidential messagesâ between Harry and his ghostwriter âwere destroyed some time between 2021 and 2023, well after this claim was under wayâ.
âThe position is not transparently clear about what exactly happened and needs to be made so by a witness statement from the claimant himself explaining what happened,â he said, adding that this should cover what attempts have been made to retrieve the Signal messages.
The judge said Harryâs exchanges with Mr Moehringer may have ârelated to the parts of Spare in which unlawful information gathering in relation to newspapers was discussedâ.
Harryâs barrister, David Sherborne, said in written arguments that the duke had not discussed unlawful information gathering via text or WhatsApp with anyone and that his Signal messages with the ghostwriter had been âwipedâ.
But Mr Justice Fancourt said this was âapparently contradictedâ by Mr Moehringer who previously said he and the duke were âtexting around the clockâ.
NGNâs disclosure bid is focused on uncovering any evidence that could relate to whether Harry knew he had a potential case against the publisher earlier than the legal time limit of six years before he filed his claim in September 2019.
In his oral ruling, the judge said he had âreal concernsâ this issue was being âinadequatelyâ dealt with by Harryâs legal team, adding that the majority of searches for material had been carried out by the duke himself rather than lawyers.
He said Harry had âonly disclosed five documents as being relevantâ to issues to be considered at trial, describing this as ârather remarkable and gives me cause for concern about the disclosure exerciseâ.
The judge also granted NGNâs request that Harryâs former solicitors at law firm Harbottle & Lewis and members of the âroyal householdâ â Sir Clive Alderton, private secretary to the King, and Sir Michael Stevens, the keeper of the privy purse â should be written to to request material relevant to the litigation.
Earlier on Thursday, NGNâs barrister Anthony Hudson KC claimed Harry had to be dragged âkicking and screamingâ into allowing his personal emails to be examined for potential evidence.
The court heard some 11,570 emails from the dukeâs now-closed ha@sjpkp.com email account were being reviewed for potential disclosure by his lawyers over the course of 150 hours and at a cost of ÂŁ50,000.
Mr Hudson accused Harry of âobfuscationâ and creating an âobstacle courseâ in the face of NGNâs efforts to source more material.
In written arguments, he said the loss of the Signal messages with the ghostwriter âgives rise to real concern as to whether the claimant has complied with his obligation to preserve potentially relevant documentsâ.
Mr Sherborne said NGN had wrongly characterised his approach to disclosing material, accusing the publisher of embarking on a âclassic fishing expeditionâ for potential information that was âentirely unnecessary and disproportionateâ.
He said accusations that Harry was putting up obstacles was the âheight of hypocrisyâ, telling the court that NGN had previously deleted âmillions of emailsâ as a way of âhiding incriminating evidenceâ.
In written arguments, Mr Sherborne said Harry had âgone above and beyond his obligationsâ and had already searched his Californian home for material.
He said Harry no longer had laptops, mobile phones or data backups from before September 2013.
The dukeâs Hotmail email address used before 2014 had been deactivated, he said, while there were âno relevant social media accounts that fail to be searchedâ.
Royal aides had also been contacted and âhave confirmed they do not hold relevant documentsâ, Mr Sherborne added.
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