They’re the kind of stories coming from that one mate of yours down at the pub. Stories that are great over a few beers, but they’re so far-fetched everyone believes they’re just not true. Think George Costanza, for instance. Or Jay from the Inbetweeners.

Kerry Packer’s life sounded a bit like that.”That’s where my family started from: 10-bob on a race course,” was one of his most famous quotes. His antics are so outrageous, so over the top, that you’d struggle to sell his stories for a biopic. He was a larger-than-life character, a high roller willing to risk big, someone who didn’t apologize for who he was.

He was an executive, a billionaire, a gambler. Someone who wore a suit, but wasn’t boring in the boardroom (or out of it, for that matter). These are the stories that defined his character and built his legend.

Flipping for Fortune

This one is one of the most famous Kerry Packer stories which sounds like one of those jokes when an Englishman, Irishman, and Australian are sitting at the pub… It’s so embedded in the zeitgeist that it’s almost an urban legend. But whatever really happened, it captures his spirit perfectly.

According to Mirage Resorts head honcho Bobby Baldwin, Packer was minding his own business, gambling at a table. In walks a Texan with a loud mouth, wanting to join.

Packer gives him a polite no, which the Texan takes offense to. He starts giving it large, mentioning his net worth of $100 million. With a slight grin, Packer pulls a coin out of his pocket and nonchalantly says, “I’ll flip you for it.”

The Texan walked away with his tails between his legs, quietly joining another table.

Vegas Escapades

Packer was notorious for making quick trips to casinos all over the world. He was a businessman first and foremost, but when he gambled, he gambled. And of course, he loved making a stop in Las Vegas every once in a while.

His 1994 stay at MGM Grand is a golden story for Packer, but a dark day for the Casino. He was once on such a hot streak that he played seven blackjack tables simultaneously. The casino, eager to stop the bleeding, allowed him to up the stakes to $500,000 per hand.

The odds, the mere nature of mathematics would stop him, right? You know where this is going. By the end of his run, he was up $26 million. Legend says he left a $1 million tip for the croupiers.

Of course, his visits to the casino weren’t just about gambling with reckless abandon. He was also heavily invested in the casino business, both in Australia and abroad. He effectively controlled almost half of the market in the country, when he set his sights on a Sky City takeover.

In 2002, Packer was believed to have bid for the New Zealand hotel and casino operator SkyCity. He wouldn’t see his bid succeed, however, with failing health leading to his death just three years later.

He was a maverick, a big gambler, but also, plainly speaking, a smart guy. No doubt he would have had a big finger in the online casino pie at Sky City or elsewhere.

“Packer here…”

Back in the 1980s and 90s, these were the words that would send a chill down the spine of horse racing bookies. Because when Packer wanted to place a bet, it was downright dangerous for business.

He loved attending the big events in Australia, with the Melbourne Cup top of his list. In 1997, he put $1.5 million on Might And Power to clinch the Cup. He promptly did, with several bookmakers almost having to close their doors after paying their dues.

His bets at the races were often so big that bookies had to pool their resources to take just a single Packer bet. He was often single-handedly responsible for doubling or even tripling bets taken for a given race. And these were big figures, with takings going into the double figure millions.

Anonymous Donations

With some, Kerry Packer has the reputation of being a loud-mouthed billionaire, a typical product of his sort, a Trump-esque bully who let his money do the talking.

There is a kernel of truth to that. But for one thing, Packer never wanted to go on The Apprentice, he didn’t want to (always) be front-page news. His anonymous philanthropy has become part of Reddit lore, with users sharing crazy stories on the regular. We’ll leave you with a couple of our favorites:

Full Ride Scholarships. He used to pay for one child per year from a disadvantaged background to attend a super exclusive Sydney boarding school, full ride, for 4 years. He not only paid the bills, but he also cared about the fate of each and every one of them.

Heart attack thank you. When he had a heart attack, the ambulance that tended to him didn’t have all of the necessary equipment. They still saved him, but he made sure to donate enough cash to fund the equipping of all ambulances in NSW (costing him $5 million).

$80k tip. He once tried to give a croupier an $80k tip. Unfortunately, she wasn’t able to accept because of ‘rules’. He goes to her manager, forces him to fire her, gives her the tip, and then asks the manager to hire her again. Not bad for a night’s work, eh?

No moral judgments will be made here, this isn’t the place for it. We have to appreciate aspects of his personality, his notorious tales, and how he did good deeds in the background without seeking publicity.