By the end of 2013, Roy Spagnolo was in a bit of a pickle. He'd failed in his attempt to wrest back control of his beloved Eels from usurpers and more of his property development businesses had followed a familiar path of going down the gurgler, owing the Tax Office millions.

On top of this, he was the subject of an investigation as to his role in the creation of 186 fraudulent memberships set up to try to win the May 2013 Parramatta Leagues Club board elections.

Spagnolo, an Eels tragic whose car sports the numberplate "Parra", ran the wealthy club from 2009 until he lost a bitterly fought election in 2013.

To add insult to injury, the Office of Liquor and Gaming commenced an investigation into allegations that Mr Spagnolo and the former Eels chief executive Bob Bentley were involved in attempted membership tampering.

As Fairfax Media's Chris Barrett reported at the time, Mr Spagnolo was in Mr Bentley's office at Parramatta Leagues Club in April 2013 when a phone call was made to the supplier of their membership software system, Aristocrat, seeking instructions on how to backdate records.

"What they did not realise," wrote Barrett, "was that every entry they made on the club's membership software program, backdating dozens of memberships and making up others, was being recorded on a backup system."

Among those to have had memberships created in their name and backdated were Spagnolo's brother-in-law Patrick Agostino, friend Roy Mittiga​, who was jailed in 1992 over insurance fraud, former friend George Gaitanos​, whom Spagnolo is now suing, Vince Lombardo​, who provides the team with free drinks and meals at his Brisbane pub, and bankrupted real estate agent Pat Sergi​, who was named at the Woodward royal commission into the late crime boss Robert Trimbole's marijuana activities in Griffith.

In 2009, a Fairfax Media investigation revealed that Mr Spagnolo had an extraordinary run of bad luck as a property developer, with eight of his property development companies failing, leaving debts to tradesmen and more than $1 million owing to the Tax Office.

A Fairfax Media investigation can reveal that Mr Spagnolo's fortunes have not improved. Corporate documents show that more of Mr Spagnolo's companies have collapsed.

In June 2013, administrators were appointed to a company controlled by Mr Spagnolo and his friend Frank Carioti​, which had gone done the tube owing the Tax Office $2.9 million.

The previous liquidator of Mr Spagnolo's eight failed property developments, Peter Ngan​, was subsequently banned by the corporate regulator for failing to properly perform his duties as a liquidator in relation to other matters.

Replacing Mr Ngan in Spagnolo-related matters is insolvency expert Ozem Kassem​, from Cor Cordis​.

In 2013, Mr Kassem sided with small creditors, mostly friends and relatives of Moses Obeid, to accept only a few cents in the dollar in full satisfaction of their debts. This effectively wiped out the $16.6 million debt Mr Obeid's company Streetscape owed the City of Sydney. The council later had this arrangement overturned.

Mr Spagnolo is currently embroiled in a bitter legal stoush with his former close friend Mr Gaitanos. Mr Spagnolo and Abdullah Pty Ltd are suing Mr Gaitanos in the Supreme Court, claiming they are owed $4.3 million by Mr Gaitanos over property investments.

For his part, Mr Gaitanos is claiming that Mr Spagnolo engaged in deceptive and misleading conduct and was secretly running an unlicensed investment scheme using Abdullah.