Press impresario Theo Skalkos, whose barrister described him as ”one of the greatest scoundrels of all time” is in the soup once more.

80-year-old Mr Skalkos, appeared in a Sydney court last week facing assault and firearm charges after he allegedly levelled a double-barrel shotgun at a tradie who approached Mr Skalkos for unpaid plumbing work.

In December, tradesman James Hasapis, 24, went to Mr Skalkos’s Sydney premises to negotiate the matter of $23,500 in unpaid fees. Mr Hasapis told police that after he was shown into Mr Skalkos’s office, the publisher of The Greek Herald allegedly appeared with the shotgun and loaded it before pointing it at him.

Mr Hasapis went to the police who arrested Mr Skalkos, charging him with assault and failure to safely store a shotgun. He was also charged with not having approved storage for ammunition.

Nicknamed “Earthquake”, Mr Skalkos was bankrupted with debts of $25 million in 2004. Creditors included the Australian Tax Office and members of the Greek Australian community who won substantial defamation payouts from Mr Skalkos.

While Mr Skalkos paid businessman Josef Assaf $150,000 for defaming him, he did not pay Mr Assaf’s $941,000 legal bill despite being ordered to do so. Mr Assaf initiated bankruptcy proceedings.

The directors of Canterbury Marrickville Olympic soccer club also won a $685,000 payout from Mr Skalkos, which was not paid. Lawyer Simon Konstantinidis who was owed in excess of $900,000 after suing Mr Skalkos and his paper, also remains unpaid.

Others embroiled in defamation cases with Mr Skalkos include a former consul-general of Greece, who was accused of neglecting her diplomatic duties by working as a taxi driver at the behest of her new lover.

The Greek Orthodox Archbishop of Australia who was accused of “immoral behaviour” in Mr Skalkos’s paper, resulted in settlements with undisclosed payments.

Mr Skalkos was also sued by his former barrister Stuart Littlemore, QC, over $300,000 in unpaid fees. Mr Littlemore later described his former client as “one of the greatest scoundrels of all times”. Mr Skalkos will appear in court again on the latest charges on March 26.