His high profile wedding to diva Mariah Carey falling apart was just the tip of the iceberg for a horror year for James Packer.
The publicity-shy billionaire had Crown employees arrested in China and had a second failed attempt at opening a casino in Las Vegas.
And now he has been forced to retreat from his casino interests in Macau.
How did it all go wrong for Mr Packer in 2016?
This week the publicity-shy billionaire put financial markets and commentators into a spin when his Crown Resorts pulled out of a major development in Las Vegas and sold off a chunk of its troubled Macau casino venture.
It caps a tumultuous year for the mogul, in which a major restructure, planned nuptials, and a foray into a Las Vegas casino presence have all ended up on the rocks.
Mr Packer's Crown Resorts were in the midst of a massive restructure: plans to split his gaming empire into two were announced in June.
One half of the business would concentrate on Australian businesses in Sydney, Melbourne and Perth. The other, with Mr Packer at the forefront, would look after international assets in Macau, Las Vegas, Manila and London.
He toldThe Daily Telegraphat the time it would "position Crown for the next decade as we continue to grow our business and meet the needs of the emerging Asian middle class".
But it would never happen.
Meanwhile, he was rarely seen in Australia, spending much of his time in Los Angeles and Israel, attending to his family, and romantic and business interests.
And romantic interests didn't get much bigger than Mariah Carey.
The pair kicked off 2016 with a January engagement: they'd been dating for less than a year when Mr Packer presented the superstar songstress with 35 carats of diamond bling to seal the deal.
They'd seen in the New Year together in Melbourne: she publicly gushed over him as she performed at Crown in Melbourne.
"Spectacular, handsome ... I don't even have words for the man who introduced me tonight," she cooed lovingly. "We'll just say the amazing Mr James Packer."
By then, Mr Packer had been spending lots of time at his Beverly Hills home in Los Angeles, close to his ex-wife Erica and the couple's three children.
Carey had reportedly relocated to LA to Packer's home from her New York base.
But midyear, there were hints things were souring, with reports of friction and arguments surfacing as the pair holidayed in Greece.
The distractions of Carey's world tour and her reality show, Mariah's World, which the notoriously-private Mr Packer was reluctant to appear on and feared would make a spectacle of their wedding, culminated in the couple ending their relationship in October.
Sources for Team Packer reportedly claimed the breakdown was due to the reality show, her extravagant spending and diva antics. Those in Carey's corner claimed those close to Mr Packer poisoned the relationship.
There were claims she was cheating with Brazilian choreographer and backup dancer Bryan Tanaka. They've since been spotted several times together.
Mr Packer, typically, has kept silent on the split.
The detainment of 18 Crown employees, including three Australians, in late-night raids in China in October plunged Mr Packer's gambling empire into crisis.
Shares in Crown dropped 12 per cent to $11.40 as news of the arrests for alleged "gambling crimes" spread.
China's big-spending "whales" have long been a target of the gaming industry, including for Crown.
But the raids in mainland China, where soliciting high-rollers to gamble overseas could see people jailed for 10 years, put overseas operators on notice.
While advertising gambling is illegal in most of China, international gaming groups try to get around this by saying it is promoting its resorts rather than casinos.
The raids put them on notice that it might be more difficult to entice Chines whales outside to spend their money to gamble - and the hit on profits would be hard.
With 18 in prison, Mr Packer - Crown Resorts' major shareholder - broke his silence.
His priority, he said, was the employees.
"I have sought regular updates on this issue and have asked Crown to do everything possible to contact our employees and to support their families, as we await further details from Chinese authorities," Mr Packer said in a statement to Channel Seven.
"I am respectful, that these detentions have occurred in another country and are therefore subject to their sovereign rules and investigative processes."
Privately, Mr Packer knew he wasn't the only one that could see what a loss of the Chinese market could mean to the viability of his planned $2 billion Barangaroo casino in Sydney.
This week came the selldown, and the reversal of the plan to split Crown Resorts.
A drop in VIP gaming turnover, hot on the heels of those October arrests, was thought to be behind Crown Resorts' overhaul of its international operations.
The company reported its Australian VIP turnover had dropped about 45 per cent this financial year.
Crown pulled the plug on its planned development in Las Vegas, then sold down some of its stake in the multibillion-dollar Melco Crown, which operates casinos in Macau.
"These business decisions are strategic and for the long-term and will underpin the company's future over the next decade," chairman Robert Rankin said.
The Las Vegas decision which sees Crown ditch a planned 1100-room hotel-casino on the Las Vegas Strip may well hurt Mr Packer most.
It's another failed experiment in Vegas which cost Mr Packer a large slice of the family fortune back in 2008, when a disastrous foray into casinos on the glitter strip cost him an estimated $US2.6 billion as the global financial crisis hit.
In 2014, he told Forbes magazine he was glad his father, the mercurial and famously merciless late Kerry Packer, wasn't around to see that.
Asked if he was worried it would destroy three generations of creating riches, Mr Packer replied: "I don't want to answer that."
He said the global financial crisis taught him not to carry too much debt, and in 2014 his company's balance sheet was "now much more conservative than it was in 2008".
Mr Packer has spent the bulk of 2016 out of the country, but seems set to spend more time in Australian in 2017, with Crown foreshadowing a renewed focus on local investment.
"Today's announcements will maximise value for the benefit of all Crown Resorts shareholders, allowing us to redeploy capital to fund high quality growth projects as well as adopting a number of capital management initiatives," Mr Rankin said.
As he counts the financial cost of the breakup with Carey, Mr Packer, may have to look back Down Under if he wants to keep a close eye on his much-loved main game.