A bankrupt former interrogator on The Apprentice, who made millions as a property developer before the economic crisis, has begged in court for a £5 million Barclays bank loan to be written off.

Paul Kemsley, a personal friend of Sir Alan Sugar and former Vice-Chairman of Tottenham Hotspur Football Club, appeared before a New York court this week in the latest instalment of his insolvency saga.

Barclays has sought to reclaim a £5 million loan from the bankrupt property tycoon ever since he sank beneath £34 million of debts in 2012.

Despite emerging from insolvency in the UK 12 months after being declared bankrupt, he avoided repaying many of his debts after claiming that he had no more domestic assets that might be sold.

Barclays took legal action following a judge’s ruling in March this year, where it was confirmed that Kemsley’s American assets would not be protected from his creditors, including the bank and Tottenham’s current owner, Joe Lewis.

When he took out the loan in 2008, Kemsley’s personal wealth was estimated to be £180 million, meaning that he was not required to provide any security for the loan, according to legal documents filed by Barclays.

The bank began proceedings against him last year, however, after he failed to make any payments on the loan and was unable to repay the £5 million sum.

The Bank’s lawyers previously said: “Mr Kemsley has failed to make the required payments and has informed Barclays that he is unable to pay the loan.”

“As a result, Barclays has suffered a substantial loss and Mr Kemsley has been unjustly enriched.”

The tycoon, who currently lives in the USA, has resisted any to reimburse Barclays for the loan, claiming in court this week that the bank’s dogged pursuit of his finances has damaged any chances of rebuilding his former life.

Court documents have revealed that Kemsley’s lawyers sent letters to Barclay’s executives begging for the case against him to be dropped.

Letters to Chief Executive Antony Jenkins and Chairman Sir David Walker complained that the bank’s suit was “a deliberate and calculated attempt to usurp the function and jurisdiction of the UK bankruptcy courts”, reports the International Business Times.

Kemsley’s self-made development fortune meant that he was a well-known figure in London’s elite partying scene, famously pictured with supermodel Pamela Anderson on his knee before being recruited to interrogate hopeful contestants on The Apprentice.

Though his Rock property empire was estimated to be worth £180 million at its peak before the economic crash, Kemsley was officially declared bankrupt in the UK High Court in 2012.

A number of ill-advised “spread bet” investments made into the Lehman Brothers shortly after the crash lead to the Apprentice interrogator tied up in litigation with spread-betting firm Spreadax.

He was also subject to legal action after advising Chelsea and England midfielder Frank Lampard on a foreign exchange bet which later misfired.