Paul Kemsley (left), The Apprentice 'Rottweiler'
Paul Kemsley (left), The Apprentice \'Rottweiler\'

A high-living property tycoon whose savagings of TV Apprentice hopefuls earned him the nickname "Rottweiler" has asked for his debt to be written off.

Paul Kemsley, a friend of Lord Alan Sugar, has appeared in a New York court for the latest chapter of his bid to rise again.

Self-made Kemsley was a well-known face on London's party and networking circuit before the financial crash of 2008. He was snapped with '90s supermodel Pamela Anderson on his knee and gained some celebrity kudos by grilling quaking hopefuls on The Apprentice.

His company Rock Properties was initially a stellar success and built up a property portfolio worth £1bn.

Kemsley was heavily backed with massive loans by the disgraced HBOS banker Peter Cummings, the head of corporate lending, who was hit with a lifetime ban as a company director in 2012 following a long-running investigation into his stewardship of the bank's vast balance sheet. Lloyds Banking Group, which bought HBOS at the height of the crisis, had to be bailed out by the British taxpayer.

Kemsley's business interests turned sour when the credit crunch hit, leaving him unable to repay a £5m Barclays loan.

British-born Kemsley, who lives in the US, is resisting efforts by the bank to get its money back. He claims its pursuit of him is damaging his chances of rebuilding his life.

The specutacular downturn in his fortunes saw the former director of Tottenham Hotspur sink beneath £34m debts in 2012.

Kemsley was also a notoriously heavy gambler and had "whale" status in London and Las Vegas. His bankruptcy filings also lists debts of £3m to Spreadex, the spread-betting operator, £3m to the taxman and £1.5m to HBOS.

His slate was wiped clean in England when he emerged from insolvency after 12 months. UK creditors, including the owner of Spurs, billionaire currency trader Joe Lewis, lost out because of that.

Barclays' took legal action after suspicions were stoked by a judge's ruling at a court hearing earlier this year. The bank's lawyers think Kemsley has significant secret assets in the United States, a claim he denies.

Court papers reveal that lawyers for Kemsley fired off letters to Barclays executives pleading with them to call off their hunt for the cash.

Letters to chief executive Antony Jenkins and chairman Sir David Walker complained that proceedings by Barclays were "a deliberate and calculated attempt to usurp the function and jurisdiction of the UK bankruptcy courts".

Judge James Peck said Kemsley was a "bankrupt who does not live like one [with] ready access to abundant free cash".

According to The Times, Judge James Justice said he had lived in luxury since moving to the US - including a palatial New York apartment costing $15,000 a week to rent, and properties in Beverly Hills, Boc Raton and Hollywood.