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He partied in luxury waterfront apartments, surrounded himself with models and actresses, was chauffeured in BMW and Mercedes-Benz cars and "drank Dom Perignon like it was Speight's".
But the lavish lifestyle that businessman Gavin Clifford Bennett funded through a $103 million fraud has come crashing down - he is now behind bars and facing the prospect of a lengthy jail sentence.
The 54-year-old made surprise guilty pleas in the Christchurch District Court yesterday to criminal charges related to a Ponzi-style scheme, similar in style to the scams of US billionaire fraudster Bernie Madoff.
The admissions brought to an end one of the Serious Fraud Office's largest investigations in recent times.
Between April 2005 and March 2011, Bennett - then director of Datasouth Group - created false documents relating to the lease of IT equipment and fraudulently obtained about $65 million from South Canterbury Finance (SCF).
He also falsified entries in financial statements by an estimated $38 million in order to retain the ongoing finance.
The result was a loss of at least $23 million for SCF, which went into receivership and triggered a $1.7 billion bailout by the Government.
SCF preferential shareholders like Albert Makary have not seen any of their money returned. The Timaru doctor finds the actions of Bennett "hard to swallow".
"You don't expect this to happen in New Zealand, which is one of the least-corrupt countries in the world. It's distressing to see the agony of those people who have lost their life savings, and how much their lives have been disrupted."
While others were left to suffer financially, Bennett lived a life of luxury in Sydney.
A former executive of a Datasouth subsidiary told how Bennett was ferried around in chauffeur-driven BMW and Mercedes-Benz services - which cost more than A$50,000 in corporate car services.
The ex-worker told of "lavish" office parties and being whisked across the Tasman to hit Sydney hot-spots, where Bennett "drank Dom Perignon like it was Speight's" beer.
"Gavin went out of his way to make us think the business was doing well. There was no hint of anything illegal going on behind the scenes. In fact, it was quite the opposite. He lavished a lot of expense entertaining employees, throwing parties, flying the management team over to Sydney for birthday parties in his apartment."
Bennett spent $596,131 renting two luxury apartments in the Rocks in Sydney.
He outlayed $207,294 on air travel to destinations including Argentina, New York, Hong Kong, Las Vegas, New Caledonia, Rio de Janeiro, San Francisco, Paris and London.
He also spent $209,869 on clothes and apparel, including purchases at Louis Vuitton, Cartier, Chanel, Giorgio Armani, Barney's and Bloomingdales New York, Victoria's Secret, Paul Smith, Gucci, Jimmy Choo and Harrod's London.
His former colleague said that at Sydney hotspot Hemmesphere "the waitresses would be waiting hand and foot topping up champagne. It was hilarious".
The other "running joke" with Bennett's staff was his love of beautiful women. He was often spotted in trendy Sydney bars with models and actresses.
"We called them 'Gav's girls'. They would come to company Christmas parties or functions throughout the year and there would be a different girl each time," the former executive said.
"There was nothing secretive about it from his point of view. I think he quite liked the fact he could turn up with these beautiful, young girls from Australia. It was all part of the fantasy world he had created for himself."
He also spent time with Marlena Davis, a co-director of Datasouth's Australian arm.
Another executive told of an occasion when "Marlena turned up in this skimpy little dress and this new set of boobs. Gavin made reference to her having new boobs."
This news was followed by talk of whether Datasouth "owned" the breasts. "There were jokes about whether we should asset-tag them."
Bennett moved to Sydney in around 2006 or 2007, shortly after breaking up with his wife of 20 or so years, Jane.
One of the executives spoken to said he was not surprised when the SFO found irregularities within the business last year.
"I'd go out with [Bennett] for dinner and after a few drinks he'd let a few things out of the bag. When SCF started to hit the headlines, Gavin became very, very nervous. There was a noticeable shift in his behaviour.
"He admitted struggling to sleep; he was quite open to us about that. We certainly weren't aware that his nervousness was because of the scheme he had going on."
Over a six-year period, around $7.8 million was paid either to personal New Zealand and Australian bank accounts controlled by Bennett or applied to business credit cards that he used for personal expenses.
Datasouth went into liquidation last March, leaving all 31 staff out of jobs.
The executive described Bennett's situation as "pretty sad and tragic".
"All of his dishonesty is coming home to roost now."
Bennett was convicted of six representative charges under the Crimes Act relating to 900 separate incidents of dishonestly using a document and two further charges of false accounting.
He will be sentenced on May 3.