If James Packer succeeds in selling his casino business — as looks likely — it will seemingly end more than a century of the Packer family looming large over Australian business.
News emerged last week that Packer had been in talks to sell his 47 per cent stake in gaming company Crown Resorts to US casino giant Wynn Resorts, which would have netted Packer A$4.7 billion ($4.97b), roughly half in cash and half in Wynn shares.
But the deal fell apart after details were leaked to the media and Wynn retreated.
Once news broke, Wynn executives became concerned about shareholder and analyst reaction and stormed off.
Whether Wynn comes back or other buyers emerge remains to be seen, but the significance of the news is that it shows Packer is a seller and wants out.
It continues Packer's retreat from Australia. In the middle of last year he resigned from all 22 of his Australian corporate directorships.
Packer hasn't lived in Australia for several years and since 2015 has resided in Tel Aviv, Los Angeles, his ranch in Argentina, or onboard his (current) mega yacht.
Lately he has called Aspen home, from where he watched the collapse of the Wynn deal last week.
It seems he is much more comfortable away from the spotlight and scrutiny that comes with the Packer name in Australia.
In an interview with journalist Damon Kitney for his biography The Price of Fortune, Packer bravely detailed his struggle with mental health and said his hometown of Sydney was a city he is "scared" of.
"Some people handle pressure well and some don't. I don't. I don't know if that is because I am wired that way," Packer told Kitney.
"I am tired of being on this rollercoaster. I don't want to do it anymore. I'm ready to put my hands up for a few years. I really am."
A sale will mark the end of an era for four generations of the Packer family, who have helped to shape Australia's corporate landscape for more than a century.
The Packer fortune dates back to James' great-grandfather, Robert Clyde Packer who, according to Packer family lore, began his journey to Sydney and to prosperity when he found 10 shillings at the Hobart races and won enough money for a boat fare to the mainland.
RC Packer laid the foundations for the family's media empire with the co-founding of Smith's Weekly and the Daily Guardian, both now defunct but hugely popular and profitable newspapers in their day.
His son Frank Packer built on that legacy by starting The Australian Woman's Weekly and building the Daily Telegraph into a popular newspaper.
He also bought one of Australia's first commercial TV licences, which his son Kerry built into the nationwide Nine Network.
It was after his father's death in 2005 that James was able to demonstrate his own business acumen and deal-making ability.
Sensing the havoc that the internet would wreak on traditional media long before many other proprietors and executives, he sold a half stake in the Nine Network and the family's magazine business to private equity group CVC Asia Pacific for A$4.5b and sold the remainder over the next couple of years.
The deal to dismantle the media empire his father, grandfather and great-grandfather had built demonstrates what an unsentimental dealmaker James is, as does his apparent decision to put the global casino business he built on the block.
That the private equity-owned media business collapsed under the weight of its own debt a couple of years later also shows what a good price Packer got and how good his timing was.
Along with his personal reasons for wanting to get out, the For Sale sign on Crown might be another example of Packer's prescience.
One possibility is he believes that land-based gaming has had its day and its profits will be eaten away by online gambling in the same way the internet devastated the family's media empire after he sold it.
Wynn Resorts may or may not be back for another go at Crown Resorts, but even if they don't return, Packer wants out and Crown will almost certainly be sold in the next few months.
Certainly investors think so — shares in Crown jumped about 20 per cent after news of the Wynn deal emerged and remain 9 per cent higher in anticipation of a new deal.
The question is whether or not that will spell the end of James Packer the businessman.
He might decide to retreat from corporate life, stay away from Australia and lead the life of luxury that several billion dollars can afford.
His A$200 million, 108m-long luxury "gigayacht" is having the final touches put on it and with a cinema, gym, sauna, large heated swimming pool, a fire pit, and private quarters for Packer, there would be little need to set foot on land ever again if he didn't want to.
Alternatively, we might not yet have seen the last of Packer the business-builder and dealmaker.