With a renowned eye for picking talented colts and fillies, and a track record that includes victories in some of the country’s premier races, Anthony clearly inherited plenty of Bart’s horsemanship. But while his father was able to train until soon before his death at age 87 in 2015, Anthony’s plight threatens to put him out of the game.

“Anthony is one of those blokes, he acts as if he’s got unlimited money sometimes,” said Harvey, whose horses with the Sydney trainer have included the mare Libertini, which was co-owned by ad man John Singleton and ran in The Everest, the world’s richest race on turf.

“He buys horses, he thinks he can sell them, and he mostly does, and sometimes he doesn’t. So when he doesn’t, he ends up with these horses, and he can’t make them pay for themselves.”

In the same week that Anthony had his credentials revoked, he spent $250,000 on a filly from champion sire Zousain and a colt by Yes Yes Yes, a winner of The Everest, at the Inglis Classic Yearling Sale. Last month, he paid $400,000 for a filly by prized stallion Extreme Choice at the Magic Millions Yearling Sale on the Gold Coast.

By then, the extent of his financial issues had been laid bare in a liquidator’s report on the winding up of his training business Rosscarbery Holdings in August last year. Issued in November, it said the Australian Taxation Office had pursued his company for debts of $1.3 million, a further $797,399 was due to other creditors, and there was $155,128 in unpaid superannuation to employees.

Those who were owed money were understood to include the kind of suppliers trainers regularly use, such as farriers and feed providers.

Concern about the demise of Cummings’ business was such that on-track winnings were withheld for two months late last year to ensure staff and industry participants were paid.

It wasn’t Anthony’s first rodeo. According to financial records filed with the Australian Securities and Investments Commission, his previous training company Something Fast Pty Ltd was placed into liquidation in 2019 with $1.5 million in liabilities.

Anthony’s stable of 50 horses was in good form in the lead-up to him being stripped of his licence, and it was only last October that he collected his 32nd group 1 winner with rising stayer El Castello in the $2 million Champion Stakes at Randwick.

However, a lean period before that was a decisive factor in his financial plight, according to his own external accountant, indicating a reliance on winners to keep his head above water.

The accountant told the liquidator that “the performance of the racing thoroughbreds declined and thus reducing the trainer’s prize money percentage”. Clients had also paid more slowly due to Australia’s cost-of-living crisis, and “both these events had significant impact of the cashflow of the business”.

Racing NSW viewed the issues with paying staff in a particularly poor light, conducting a fit-and-proper person test to assess Anthony’s suitability to continue as a trainer before taking away his licence.

Anthony declined to comment for this story but has vowed to try to overturn the ruling.

“I’m just mystified about the whole thing,” he told owners in an audio note last week. “I’ve done nothing wrong. I haven’t broken a rule. I’ve acted within the rules of the land. I just don’t get it.”

He will contest the decision against him at the independent racing appeals tribunal, which is headed by former NSW Supreme Court judge Geoffrey Bellew.

It is far from his first legal fight.

In 2016, he was involved in a family dispute over the division of Bart’s multimillion-dollar estate, which reached the Supreme Court before being settled.

Earlier, Anthony endured a bitter two-year court battle against Nathan Tinkler after their 18-month partnership blew up when he baulked at the mining magnate’s proposal that he train exclusively for him.

There was a settlement with the former young billionaire, with Harvey stepping in to play peacemaker at a lunch in Paddington in 2011, three years before an embattled Tinkler sold his Patinack Farm racing empire.

But Anthony’s decades-long friend Julia Ritchie, another prominent owner and breeder, believes that period was a major pivot point for him.

“It was not a problem he was ever going to be able to dig himself out of,” said Ritchie, who has had winners with Anthony in group 1 races such as the Victoria Derby, TJ Smith Stakes, the BMW (as the Tancred Stakes at Rosehill was formerly known) and, most recently, with El Castello four months ago.

Ritchie, who was the first female board member of the Australian Jockey Club before the merger that established the Australian Turf Club, first met Anthony at a sale in New Zealand when they were just out of their teens. Her father, Bill, who made a fortune manufacturing women’s footwear, had horses and was friends with Bart, and she and Anthony dated for a time.

That didn’t last, but her close association with him did. She has lent him money – the liquidator’s report details a loan by a company of hers in 2019 to help him buy a horse float – but she said he had always paid her back.

“Anthony is possibly one of the most intuitive trainers I’ve had the pleasure to work with, and I think he knows how to pick a horse for talent, a mile away,” she said. “It’s something that I think is in the gene pool of the Cummings. It’s just the business structure that goes around it … but I’m still very loyal to him, I still support him. I have supported him every step of the way over the last 40 years.”

With owners and their horses in limbo, Anthony’s 38-year-old son Edward has sought to take over the operation at Leilani Lodge, applying to Racing NSW’s licensing committee to be approved as a metro trainer, having previously trained at Hawkesbury but having handed in his licence to work as his father’s foreman.

While the ATC, which runs Randwick racecourse, has given Edward approval to take over at Leilani Lodge on an interim basis, the prime location will be opened up to other suitors after the autumn racing carnival in an application process to determine a new tenant.

But if Edward is not granted a metro licence to train at the 56-box facility, the Cummingses and the dozens of horses they have in work could be forced out as soon as next week.

After half a century there, and with their surname synonymous with the place due to Bart’s fabled exploits, that would be a terrible shame, Ritchie said. “I do think having a training business or a [racing] culture in Sydney without a Cummings would be a long-term historical loss,” she said.

They have the best of racing bloodlines. But this time that may not be enough to save the day.

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