The reclusive billionaire owner of the Daily Telegraph could be sent to jail after allegedly failing to pay his ex-wife £50m in one of the biggest divorce settlements in UK history. Sir Frederick Barclay’s ex-wife has asked a judge to commit him to prison after claiming that the businessman had failed to make payments ordered by the high court. Lady Hiroko Barclay said 87-year-old Sir Frederick was in contempt of court and accused him of breaching orders relating to the payment of money and production of documents. Earlier this year, Lady Barclay was awarded a settlement of £100m following the breakdown of their 34-year marriage. She now says Sir Frederick has failed to hand over the first half of the money and to produce relevant material. Lawyers representing Sir Frederick indicated that he would mount a defence. Sir Frederick, together with his deceased twin brother Sir David, built a business empire that included the Ritz hotel, the delivery business Yodel, and the online retailer Very Group. The pair also gained enormous influence in rightwing politics through their ownership of the Daily Telegraph and the Spectator – in addition to building a castle on their own tax-haven island in the Channel. However, relations within the family soured in recent years. This summer Sir Frederick settled a legal case against his nephews, who, he claimed, were secretly recording his conversations using a bugging device hidden in the conservatory of the Ritz hotel. Lawyers representing Sir Frederick had argued that Lady Barclay’s application should be considered in private, as evidence relating to confidential financial information would be aired. Judge Jonathan Cohen dismissed that application and said hearings would be staged in public, but he indicated that it might be necessary to hear some evidence in private or impose reporting restrictions. He said the final hearing would be staged early next year. The judge criticised Sir Frederick in a ruling in May, saying the businessman had behaved in a “reprehensible” fashion during the dispute. Sir Jonathan said Sir Frederick had sold a luxury yacht and “applied the equity for his own use” in breach of court orders. The judge also said Lady Barclay had originally asked for £120m and Sir Frederick had made an offer that might have led her to getting nothing. Stewart Leech QC, representing Lady Barclay, said she was now applying for Sir Frederick to be committed to prison for breaching an order to produce documents and pay the first £50m of the settlement. Charles Howard QC, who represented Sir Frederick, said Lady Barclay would have to show her ex-husband had the “means to meet” the demand for £50m and prove he had “wilfully refused or neglected” to pay. Both Sir Frederick, who is rarely seen in public, and his ex-wife were in court for the hearing. The judge said Sir Frederick’s application for the hearing to be heard in private was “plainly unsustainable” but he would consider a request for a future committal hearing to be held remotely because of Sir Frederick’s age.