A high-flying eastern suburbs real estate agency has spectacularly come undone, with its director blaming the collapse on an alleged betrayal by his best friend and assistant he once trusted with his business affairs and personal bank accounts.

Former Double Bay agency Trelease Associates Property Management (TAPM) and its trustee company, Daniel Trelease Pty Ltd, have fallen into voluntary liquidation owing almost $2.6million to unsecured creditors, according to documents lodged with ASIC.

The agency's director Daniel Trelease is pursuing Supreme Court action alleging his former executive manager, chief financial officer and personal assistant Jacqueline Clow (nee Reidy) secretly siphoned more than $675,000 from the business - claims that cannot be tested against her because she died suddenly last year.

Court documents allege the claimed losses ultimately pushed the once-thriving agency, which was based in Mosman and Double Bay, over the edge.

Mr Trelease began legal proceedings against his former right-hand woman for allegedly breaching her employment contract after she resigned in January 2024, following more than six years with the company.

According to his statement of claim, the UK-born Clow had what Mr Trelease described as 'exclusive access' to both his business and personal online banking accounts.

He alleges that she changed banking passwords and refused to provide them, despite repeated requests for access to the accounts.

Long before her name surfaced in Supreme Court proceedings, Clow was better known in Sydney as one half of one of the city's most recognisable hospitality couples.

She was married to Irish publican Donnacha Reidy, who owned iconic Sydney watering holes including Kitty O'Shea's, The Republic Bar, Trinity Bar and the Fox and Lion Hotel.

Throughout the late 1990s and early 2000s, the pair were regular faces on the racing and social circuit, rubbing shoulders with the hospitality elite before their marriage eventually came to an end.

Following their split, Mr Reidy relocated to Western Australia with the couple's two daughters.

Friends say Clow later moved to Kiama, on the NSW south coast, with her younger partner, builder William Clark, for what they described as 'a fresh start'.

'She lost contact with a lot of her extended friendship circle [from Sydney] when she moved to the south coast with Will,' one long-time friend said.

'These allegations are shocking and certainly come as a surprise to anyone who knew her.

'There has to be more to it. It just doesn't sound like the Jacquie we all knew.'

The already extraordinary dispute over Trelease Associates' collapse took a tragic turn when Clow died, at the age of 58, just months after legal proceedings were launched against her, according to documents lodged with ASIC.

In an online tribute following Clow's death in March 2025, Mr Clark wrote of losing 'my beautiful lady'.

'So long ago in a time when we were so free, like my Queen Bee you were and forever will be my Queen Bee, flowering in full bloom,' he wrote.

'You left me too early... I miss your smile and face every day.'

It is believed that Mr Clark has since fallen out with Ms Clow's two daughters following her funeral. 

Mr Trelease told the liquidator he had placed 'complete trust and confidence' in Clow throughout her employment before later concluding that she had allegedly 'embezzled' a significant amount of company funds.

'Ms Clow is since deceased and cannot pursue further detail,' the report states.

ASIC documents show the failed companies owed creditors about $2.58million, including almost $85,000 to the Australian Taxation Office.

Mr Trelease attributed the collapse to what he described as 'recently found out fraud', 'theft and malfeasance', and his own 'poor management and oversight'.

The liquidator, however, also pointed to broader business problems including undercapitalisation, declining revenue, inadequate cash flow, poor management of accounts receivable and mounting tax liabilities.

His report identified potential uncommercial transactions, unfair loans, unreasonable director-related transactions and possible insolvent trading dating back to July 2020.

'The trust incurred high levels of debt over time, which became unsustainable in the context of declining revenue,' wrote administrator Jamieson Louttit.

'There was a downturn of property sales and the company failed to meet creditor expectations.'

Mr Trelease, who was rumoured to have 'disappeared' from Sydney and even gone overseas following the collapse of his business, has since returned to the eastern suburbs, sources say.

'He's now working in Rose Bay and seems to be doing well for himself,' a former staff member told the Daily Mail last week.

His new company website describes him as 'the former owner of a top buyers agency in the eastern suburbs', adding that he built 'a reputation for client satisfaction, confidentiality and professionalism'.