The charges were brought by detectives from the State Crime Command’s fraud and cybercrime squad, who are investigating how $5 million worth of Australia’s best wines vanished amid the wreckage of Mr James’ liquidated Hunter Valley wine empire.

The former James Estate Wines boss appeared in the Downing Centre Local Court on Thursday making an application to have his strict bail conditions relaxed.

The court heard the former high-flyer, who is living with his elderly mother in New Lambton and collecting Centrelink benefits, has “six or seven other” court cases on the go. These include matters in the supreme, federal, family and local courts.

It’s been a tough few years for Mr James. 

He is being pursued by banks for more than $10 million after the collapse of 12 companies in his wine and publishing empire.

The 55-year-old is negotiating a bitter divorce settlement with his estranged wife Trudy James that took a big-dollars turn for the worse this week when receivers exchanged contracts for the sale of the couple’s former family home for about half of its original $8 million asking price.

And on Thursday Mr James faced what Judge Graeme Henson described as “significant” charges of attempting to pervert the course of justice by harassing Mrs James about her involvement in a police investigation.

Counsel for Mr James, Ann Bonnor, said her client had been “under investigation for some time”.

Ms Bonnor successfully challenged an application to have the local court matters moved to Newcastle on the grounds that Mr James needs to be in Sydney regularly to see lawyers because he is juggling so many court matters.

But Judge Henson rejected an application to remove a curfew that requires him to be at his mother’s house in Newcastle each night from 11pm to 6am. 

While Mr James was in the Sydney court, Mrs James received a notice to vacate the Whitebridge mansion she owns that is being sold as part of the couple’s messy divorce settlement.

Killara, set on 8631 square metres, is modelled on Tomago House where Mr James grew up.

Mrs James is fighting the cut-price $4.2 million sale done at the behest of court-appointed receivers Ben O’Hearn, of O’Hearn Lawyers, and Bruce Heathcote, of Forsythes Business and Financial Advisors.

“My worst nightmare was that they would undersell the house and I’d be thrown out with nothing,” she said. “It’s come true. I feel like I am being punished for talking out about this.”

The $4.2 million offer for the property was just $200,000 more than Mrs James bought it for more than 15 years ago when it was independently valued at $3.8 million.

Battling to stay solvent, Mrs James plans to challenge the sale. 

"How can the value go up by $200,000 in 15 years? It just makes no sense," she said.

Several real estate insiders who spoke to Fairfax Media expressed surprise at the cut-price deal for Killara, one saying the property – that had sold signs out the front on Tuesday – had been "snapped up for a song".

Another said it was the Hunter's most contentious real estate deal of the year.

According to documents seen by Fairfax Media, Mark Kentwell, joint selling agent of PRDnationwide, put a "conservative estimate of the selling price" for the property in July 2016 between $7.5 million and $8.25 million. 

In May, Todd Hadley, of MJD Valuers, put the price of the property at $7 million. 

But the trophy home failed to sell at a public auction last week after bidding opened at $3 million and went between two registered bidders before being suspended at $3.6 million.

The receivers, who did not respond to repeated requests for comment, have Killara insured for $9.1 million.