In the late summer of 2017, Melbourne-based investor Craig Astill ventured to the Northern Territory to spend a few days at Aileron Station, a major cattle farm sprawling over a million acres just 130 kilometres from Alice Springs.

During the trip, the 54-year-old marvelled over the farm’s oasis-like vista: bright-green grass and brimming dams set against the backdrop of Central Australia’s endless red dust desert. Astill’s investment firm, Caason Group, had acquired the significant property two years earlier for an undisclosed sum.

While Caason Group, founded by Astill in 1999, held a diverse portfolio – from telecommunications to mining to fintech – there was no doubt Aileron Station was its crown jewel. So much so that in 2021, Astill led the purchase of neighbouring hay farm Oolloo Farm for $6.1 million.

The spoils of Caason Group’s success over its 26-year lifespan afforded Astill and his family a life of opulence. He vacationed in beachfront villas in the Maldives and carved turns on the Val d’Isère slopes of the French Alps. He showcased renovations of a multimillion-dollar home and was known to drive luxury cars through the streets of Melbourne’s affluent inner-east suburbs.

Astill couldn’t know it during that 2017 trip up north, but lenders would eventually seize possession of the Aileron and Oolloo farms, selling them to rich-lister Charlie Shahin. It was an event dubbed by sources unable to speak publicly as the beginning of the end for Caason Group and Astill’s life of luxury.

The Melbourne investor now faces serious questions about the management of his firm, whose key subsidiary collapsed with just $75 in its bank accounts, minor share holdings in two collapsed mining companies, and two luxury cars – a $75,000 black Maserati coupe and $50,000 black Land Rover wagon.

Astill is subject to ongoing scrutiny from the corporate cop, and a long list of investors and creditors furious over money they are unlikely to ever see again. He was declared bankrupt last month with a $10.7 million debt pile mounted from excessive borrowing, business failures, legal action and gambling.

As liquidators, receivers and administrators trawl through Caason’s various insolvent companies, a murkier picture of the firm’s operation has begun to emerge. Alleged misconduct has been identified. Millions of dollars have been lost. Lucrative metal rods, gold bullion and precious mineral sands purportedly owned by Caason and used to secure loans, have either not been found or are owned entirely by another company.

The firm’s key entity, Caason Investments, entered liquidation in November after a lengthy court battle with a $24 million hole in its balance sheet. It owes 108 creditors an estimated combined total of $4.7 million. They range from private lenders to individuals with personal relationships with Astill and his family.

Caason Investment liquidator Adam Preiner determined the company traded while insolvent from at least June 30, 2021, leaving Astill liable to the tune of $3.5 million. The creditors’ report, filed to the Australian Securities and Investments Commission in February, detailed $18 million in loans to Caason Group’s related companies, Astill himself, and his wife. Preiner also identified several potential offences, which he indicated were detailed in a confidential report sent to ASIC.

Questions have also been raised about the firm’s commercial associations, which included twice-bankrupt mining spruiker David Catsoulis, self-described “Christian marketplace leader” Dave Hodgson – who has been sued twice by ASIC – and previously banned director Colin Oxlade.

Astill told the liquidator in November that Caason Investments had operated an “innovation, research and development and project management investment business”.

Preiner’s investigation, however, painted a largely different picture: “My investigations have identified that [Caason Investments’] predominant activity was borrowing funds from private investors and lending the borrowed funds to related entities of the company,” the liquidator stated in his report.

The Australian Securities and Investments Commission is investigating Astill and his companies amid the litany of concerns identified in reports filed to the corporate regulator by liquidators, a well-placed source unable to speak publicly confirmed.

The regulator declined to respond to detailed questions, but said: “ASIC is aware of the concerns involving Caason Group and is considering them in line with our normal processes.”

The corporate cop has already charged Astill. In December, the investor fronted Sydney Downing Local Court on two counts of failing to lodge a key report directors are required to file during the insolvency process, known as a Report on Company Activities and Property (ROCAP).

The charges, launched by ASIC, were related to Aileron Station and Oolloo Farm. Astill eventually submitted the two ROCAPs. He was fined, and no conviction was recorded.

When contacted by this masthead, Astill insisted on sitting down for an interview but on the day it was scheduled his solicitor responded, questioning the public interest of the story and revoking the offer of speaking to his client. There was no response to detailed questions sent later to Astill and his lawyer.

The firm’s collapse, and Preiner’s findings, have been a long time coming for some creditors, several of whom launched a series of court proceedings last year in a bid to wind up several of its key entities after Caason defaulted on repayments. But applications to wind up some of Caason’s companies go as far back as 2020.

Some creditors who spoke to this masthead on condition of anonymity expressed sympathy for Astill, placing the blame on the private lenders Astill sourced financing from.

“He’s straight up, [before this loan] he’s paid me back – apart from this it’s all been good,” said one investor, who met Astill over a decade ago. The creditor has written off the six-figure loan made out to Caason about five years ago.

Others are not angry the business failed, but rather that Astill failed to act as his companies continued to incur losses and defaulted on repayments. Instead, they claim, Astill obfuscated and denied creditors’ concerns, leading to an increase in debts and the unlikelihood of any sort of return.

“Craig had a moment when he realised he f----- up – he could’ve copped it, but instead he decided to weave a web of deceit,” one creditor said.

And then there are those with more serious concerns, who feel deliberately misled. This includes creditors whose loans agreements, several of which have been obtained by this masthead, were supposed to be secured by collateral that liquidators say they have been unable to locate or if located, were owned by another company. These include the precious metal rods, gold bullion and mineral sands.

Until his bankruptcy, Astill continued to operate various Caason Group entities and in October, he appeared as a speaker on an online forum discussing success in agriculture, despite the litany of financial woes, court proceedings and angry creditors.

Astill stated in his bankruptcy documents his insolvency was due to “excessive borrowing, business failure, legal action, and losses from gambling”.

Astill’s bankruptcy trustee, Gavin King, found that Astill owes at least $10.7 million, according to his initial report to creditors. His bank accounts are overdrawn by $20,000, and a SportsBet account held a little over $156. There are no other assets, and – like Caason Investments – Astill’s personal creditors are unlikely to recoup any of their funds.

Many of Astill’s personal creditors were private investors to the Caason Group, whose loans were secured by personal guarantees provided by the Melbourne businessman.

Curiously, the largest creditor of Astill’s estate is an entity called Castill Investments – incorporated by Astill a month before he applied for bankruptcy – which is owed $4.2 million.

One investor, owed over $150,000, has breathed a sigh of relief that Astill is banned from managing companies now he is bankrupt. “I play high-risk games, and you don’t win all the time and that’s fine, but … you expect people to be straight up. Craig wasn’t,” the investor said.

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