Simon Anquetil, one of the alleged conspirators in the $165 million fraud on the ATO, racked up $100,000 on his corporate American Express card on strippers and escorts in a four-month period.
Prior to his alleged involvement in the current payroll fraud, Mr Anquetil was the managing director of an IT company which went into liquidation.
He was grilled in the Federal Court about his use of a "dummy" director to avoid personal liability for the thousands of dollars per week he spent on strippers.
In July 2013 Michael Hayter from law firm Gillis Delaney quizzed Mr Anquetil about the $100,000 he clocked up on his corporate American Express card before his IT company eStrategy Group went belly-up.
The court heard that Mr Anquetil spent $63,000 at the Bada Bing strip club in Sydney's Kings Cross in a four-month period during 2011.
On one occasion he spent $12,000 in one day at an escort agency called First Ladies of Collins Street, which is in Melbourne's CBD.
"You seriously think that it's appropriate that you would claim as a company expense $12,000 for one day taking a client to strippers?" - "I wasn't getting anything out of it," replied Mr Anquetil who claimed that he thought it was pole-dancing rather than prostitution involved.
"Pretty good pole-dancing for $12,000" said Mr Hayter.
Mr Anquetil claimed the credit card bills at places such as Twin Peeks, Men's Gallery and Pure Platinum were entertainment for clients. When pushed to identify the clients he named a Melbourne property developer, a pharmaceutical boss and a Macquarie banker.
When Mr Anquetil's company went into liquidation in September 2012, owing American Express $100,000, the court heard that Mr Anquetil had already sent up a new company, called eStrategy Operations (as opposed to Group). The new company used the same office, the same equipment and the same clients.
Mr Anquetil was examined about what he had told his "boss" about his spending.
His boss, the company's sole director, was listed as Jamaica Gibson, who was described as a 22-year-old Indigenous woman with two young children and no business experience.
He denied that she was a stripper but he did agree that it was his handwriting that had recorded Ms Gibson being of "no fixed address" on eStrategy's report to creditors.
Mr Hayter asked if he had reported back to his "boss" that the thousands of dollars spent weekly was because he took clients "to pole dancing and women take their clothes off and that's how I get work out of them".
On Friday, Mr Anquetil was released on bail after being charged with conspiring to cause loss.
Central Local Court heard he "returned voluntarily from overseas" on Thursday and was "apprehended" by the AFP at Sydney airport.
Police allege he was one of seven co-conspirators in a $165 million tax fraud syndicate involving Plutus Payroll, a company he formerly chaired.
The 34-year-old St Aloysius' College old boy appeared via audiovisual link dressed in a patterned short-sleeved shirt and agreed to strict bail conditions, including using only one mobile phone and not associating with his co-accused, who include the son and daughter of the deputy tax commissioner, Michael Cranston.