He is close friends with Sir Philip Green, Joe Lewis and Mike Ashley and was once photographed in a clinch with Pamela Anderson at a party at the Planet Hollywood Resort & Casino in Las Vegas. More recently, he has gained fame as Sir Alan Sugar’s “rottweiler-in-chief” during the interview stage of The Apprentice.

But last night’s episode of the popular television show, featuring the infamous “job interview from hell”, saw the introduction of a new interrogator after Paul Kemsley, the property tycoon and former Tottenham Hotspur vice-chairman, declared himself unavailable “due to other commitments”.

It emerged yesterday that, at the time of filming, Rock Investments, Mr Kemsley’s £500 million property empire, was teetering on the brink of collapse. Last Thursday, his efforts to save the business he founded in 1995 ended in failure and administrators from PricewaterhouseCoopers (PwC) have taken control. The group, which PwC said had fallen victim to “the well-documented slowdown in the property market”, has 40 properties in the UK, two office blocks in Manhattan and a villa development in Turkey. The assets include the former Burberry headquarters on Haymarket, London, Crystal Palace’s Selhurst Park football stadium, the Anchor retail park in Burnley and the Regency Arcade in Leamington Spa.

Barry Gilbertson, PwC’s real estate partner, said that, in the light of the slump in property prices, the firm intended to continue managing the portfolio and there was no question of a “fire sale”. He confirmed that Mr Kemsley, who now lives in America, had not made any approach to buy back the business or any of its assets.

The collapse of Rock is the latest reverse for Mr Kemsley, who was estimated to be worth £180 million in last year’s Sunday Times Rich List. Last year he was embroiled in litigation with Spreadex, the spread-betting company, after placing several huge bets the week before the collapse of Lehman Brothers that the bank would recover. He also advised Frank Lampard, the Chelsea and England footballer, on a foreign exchange punt that went wrong and became the subject of legal action.

Mr Kemsley, 42, who could not be reached for comment, left school aged 17 to work at a firm of surveyors, but later worked for Mr Ashley’s Sports Direct chain.

Like the Newcastle United owner, he is a lifelong football fan and until 2007 was vice-chairman of Spurs, whose chairman, Daniel Levy, was a director of Rock up until last week’s collapse. Mr Levy and Joe Lewis, the Bahamas-based billionaire who controls the Premiership club, were among Rock’s original investors in 1995.

It is understood that Mr Lewis ceased to be involved with Rock after it set up a joint venture with HBOS two years ago with plans to build up a £1 billion property portfolio. In addition to providing equity funding, the bank is thought to have supplied about £500 million of debt to Rock.

Mr Kemsley is well known in the property world for his aggressive tactics. In an interview in Property Week, he said: “I think we have a reputation for being performers. If I want something, I will buy it.” One of his biggest coups was buying 27-35 Poultry in the City of London for £40 million in May 2006. Four months later he sold it for £72 million to a former Russian finance minister.

Last night, as it became clear that his strategy had gone badly wrong, PwC confirmed that Mr Kemsley “no longer had any interest in the Rock group or its assets”. Or in the words of Sir Alan: “You’re fired!”

Words of wisdom

On Sir Philip Green
‘He’s like a second father to me. He’s taught me how to deal with bankers and how to operate’

On Mike Ashley
‘One of my greatest friends and allies’

On Sir Alan Sugar
‘So focused, it’s frightening. If you have talent there, then he’ll find it’

On Lucinda Ledgerwood, 2008 contestant on The Apprentice
‘An absolute nutcase’

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