The cash targeted includes a $6 million defamation payout to Mr Alex and his murdered standover man Joseph Antoun, which was an alleged sham created for Mr Alex's troubled business rivals to buy him out of their labour hire companies.

Proceedings launched by Mr Alex's trustees in the Federal Court in Victoria claim the defamation settlement was in effect payment for the sale of his business interests, and disguised to bypass bankruptcy laws, which make defamation payouts untouchable by trustees.

The payout was significantly higher than the record set by a court in defamation claims in Australia.

The trustees are also attempting to claim money tied up in a web of share transfers and litigation settlements involving Queensland businessman Kevin McHugh, former Alan Bond bankruptcy advisor James "Big Jim" Byrnes, accountant Angelo Russo and Mr Antoun.

They claim Mr Antoun was acting as a secret proxy for Mr Alex while he was a bankrupt, enabling him to dodge bankruptcy laws and tax obligations, while receiving the proceeds of multimillion-dollar deals born of violence and threats.

Mr Alex was declared bankrupt in 2011, owing more than $1.2 million to the Australian Taxation Office.

The bankruptcy trustees – Gess Rambaldi and Andrew Yeo – started moving on the proceeds of the deals and entities associated with Mr Antoun after receiving a call from Mr Byrnes in late 2013, according to court documents tendered during a two-day hearing in Melbourne last week.

Mr Antoun was murdered in December 2013, leaving a question mark over the continued existence and control of the trust once used to funnel the proceeds of the deals.

Mr McHugh has previously given evidence that he was strong-armed into handing his company over to Mr Alex, after a 2011 meeting involving Melbourne underworld identity Mick Gatto.

"Kevin McHugh is a Walter Mitty and he should concentrate on telling the truth," Mr Gatto told Fairfax Media.

Deals struck after this time – including resolution of the alleged sham defamation case – were signed in March 2013, enabling Mr McHugh to regain control of his companies for $12 million.

But with the financial backing of Mr Byrnes, Mr McHugh later launched proceedings against Mr Alex and Mr Antoun alleging he had been coerced into signing away his company and should not have to pay the money.

At a mediation before former High Court judge Ian Callinan in October 2013, Mr Alex's bankruptcy was revealed to the other parties and an agreement setting aside the March deeds was struck, the Federal Court heard last week.

Leading up to the mediation, Mr McHugh had alleged in an affidavit that he was bashed by three unknown assailants who turned up at this Queensland office in June 2013, demanding he "do the f...ing  right thing".

Mr Alex's trustees claim three companies still owe Mr Alex and Mr Antoun about $5.5 million under the deals while another man and Mr Byrnes owe more than $3 million individually and Mr McHugh owes nearly $5.5 million on his own.

The trustees are also attempting to claim at least $3.7 million under the October deal.

Lawyers for key respondents, including Mr Byrnes, Mr McHugh and associated companies argue the March deeds are void and that they are not liable to pay because Mr Alex was not a party to the October deed.

Fairfax Media attempted to contact the lawyers for Mr Byrnes and Mr McHugh on Friday.

The trustees declined to comment while the matter was still before the courts.

Federal Court Jjudge Bernard Murphy will hand down his decision after receiving written submissions from the parties, which are expected to be filed within the fortnight.

with Chris Vedelago