The 5 most legendary gamblers ever

James Pacheco
Author, Betting enthusiast

December 18, 2023

James started working in the betting industry a few weeks before Roger Federer won his first-ever Grand Slam and a few months before Greece shocked Europe’s elite at Euro 2004.

There’s gambling and then there’s legendary gamblers. One man on this list once wanted to bet 60 million Dollars on the outcome of a coin toss, another lost almost 2 million pounds as a result of a rugby try that should have been disallowed, while another witnessed two separate deaths at the poker table in a career as a poker pro hat spanned almost 60 years.

Here are a few stories about some of the most fearless and reckless gamblers in history. As entertaining as some of them are, it should be remembered that we’re not glorifying them or their betting. In some cases, they’re a good lesson in precisely what you shouldn’t do.

Gambler in elegant suit, hat and sunglasses

Kerry Packer-Fearless

Legendary Australia businessman Kerry Packer (17 December 1937 – 26 December 2005)  was famous for many things.

A media tycoon, his family owned both the Nine Network and the publishing company Australian Consolidated Press, making him arguably the single richest and one of the most powerful people in the whole country for several decades. At the time of his death in 2004 his estimated net worth was   A$6.5 billion.

He formed the World Series Cricket which ran between 1977 and 197, which revolutionised the game in such ways as being the first cricket tournament where players wore coloured kits, where day-night games took place, and which had cameras filming the action from both ends rather than just one.

A pre-cursor to the Indian Premier League 30 or so years ahead of its time, it was one of the main reasons why cricketers went from poorly paid yet brilliant sportsmen in the 1970s to become well-rewarded for their exploits, all funded by Packer.

A keen rugby fan, he also attempted to fund the Rugby World Corporation (RWC), as a result of which the Super 12 and Tri Nations series were created, though South African, New Zealand and Australian players were warned by their Board to not take part in it without their approval and so the WRC experiment never really went ahead.

But it was perhaps away from business ventures that he really made his name… as a fearless gambler. Somewhat unsurprising given his enormous wealth, this was a man prepared to take huge risks by placing the sort of bets most of us would never even dream of striking.

Horseracing was one of his favourites when it came to a punt, but it was at the casino tables that Packer was really in his element, though results were, to say the least, mixed.

In 1990 he played at four roulette tables at a London casino by himself and lost all of the £15 million he’d walked in with. Across a three-day losing streak in 1999, also at London casinos, he lost A$28 million, considered the biggest loss ever witnessed in British history by one person at any given time.

But then there was the time he won A$33 million at the MGM Grand Casino in Las Vegas and forced the casino to temporarily close down as the casino bosses tried to come to terms with what had just happened. In a story told by former golfer John Daly who was there at the time, Packer insisted on being paid his winnings of 52 million US dollars in cash because the previous day he lost 8 million and was asked to pay up…in cash.

At the Ritz Hotel in London, he had his own private gambling room and his staple bet on a hand of blackjack was 10,000GBP. The swings were so big at the casinos he played at that the casino or holding company’s share price fluctuated wildly as he was playing, depending on which way things were going.

He may have been a ruthless businessman and over-the-top gambler, but his generosity was legendary. He thought nothing of tipping casino employees dozens of thousands of dollars after a particularly big win and once paid off a waitress’ mortgage when discovering she was working late to make ends meet and had a young child waiting at home for her after her shift.

But if one story sums up Packer best, it’s this one. At the Stratosphere Casino, a Texan oil investor crossed his path. Some say he was attempting to lure Packer into a game of high-stakes poker. Others say Packer asked him why those around him were making such a fuss about the Texan. Either way, the man told him “I’m worth $60 million!”

Packer took out a coin and challenged him to play the lot on the single outcome of a coin toss with the immortal line: “I’ll toss you for it.”

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Harry Findlay – Born to bet

Harry Findlay was probably never going to be anything but a gambler after a short spell working for a bookmaker in his late teens. What he quickly realised was that he’d rather be the punter backing the bets rather than the bookmaker laying them and for the next 40-odd years, that’s always been the case.

Like Packer he’s always been equally fearless and confident in his betting, and he’s placed thousands of bets across such sports as football, tennis, cricket, horseracing, greyhound racing, rugby and Aussie Rules.

Like Packer, his fortunes have swung from extreme highs to the sort of losses that many would never recover from.

But unlike Packer, he didn’t have a business empire to fall back on after a heavy loss or even to fund his next wager.

He was a co-owner of 2008 Cheltenham Gold Cup winner Denman alongside Paul Barber, a horse who earned over £1,141,347 in prize money, but relying on the great chestnut-coloured monster of a horse to make a living for himself wasn’t a practical plan.

At several time during his life, he’s gone bankrupt with no way out other than looking for his next bet to bail him out, if necessary, by borrowing money to gamble with. During these periods he went back to having the sort of bet most of us would, rather than the ones almost none of us would.

One of Findlay’s favourite bets was to place huge wagers on Roger Federer at Grand Slam tournaments in his heyday on Betfair when he was practically unbeatable. This was often as a big favourite meaning Findlay was risking much more than he stood to win; but that didn’t put Findlay off and the great Federer rarely let him down.

But one of his other darlings, the New Zealand All Backs (rugby union) side proved to be far less reliable and boy, did it cost him.

He put down a cool £2.5m on them winning the 2007 World Cup at odds of around 1.8 and many of his friends followed him on it, meaning that by the time they played France in the quarterfinals, plenty of other people’s money was also on the line. That included his gardener giving him £28,000 (in an ice cream tub) to place a bet on the All Blacks for him.

Despite leading 13-3 at half-time, they went on to lose as a result of a try that replays showed came from a forward pass as France ended up winning 20-18.

Luckily for him, a half-time change of heart saw him wager a further £18,000 on the French to win the game at good odds given they were behind at half-time to the red-hot favourites.

It saved him from losing £2.5 million (he lost £1.9 million after hedging the bet) and from going bankrupt (not for the first time) but it was still a bitter pill to swallow and worse still was the money lost by friends who had trusted his gut instinct. To make the story a little more bearable, his gardener had a saver on South Africa to win the World Cup and they eventually did, allowing him to recover some of his losses, much like Harry had, as well.

Of Wayne Barnes, the referee who didn’t spot he forward pass, he said: “I hated him like a Kiwi for a long time. But I watched Barnes do a game this year and I’d never seen refereeing like it. He was great.” So, no hard feelings. Well, sort of.

Four years later he clearly hadn’t learnt his lesson, backing the All Blacks to win the 2011 edition of the World Cup and this time they came good.

Again, it was France in their path but this time they held on to win 8-7 and after placing a bet for 60% of his total wealth – £230,000- he pocketed £210,000.

A huge fan of greyhound racing, a big gamble in 2013 to establish Coventry Stadium as the centre of greyhound racing didn’t come off with Findlay blaming a lack of support from the Greyhound Racing Association. He says it cost him close to £1.7m of his own money and he recovered very little of that.

A few more big bets on Australia’s National Rugby League – another of his favourite sports- got him back on track later that year and these days he carries on doing just that: scouring betting markets across any number of sports in search of good wagers. He doesn’t know any different.

But aside from all these heart-stopping stories involving huge amounts of cash, one story stands out as showing a lighter side to Findlay’s personality. For the record, it’s a story that I once heard told by a friend of mine so I can’t be sure it’s 100% true rather than something of an anecdote; but I believe it anyway.

In a limited-overs county cricket match in the late 80s, the two skippers were out in the middle for the toss. When the coin landed a voice could be heard behind them. “So, what you going to do, Mark (Nicholas, former Hampshire captain)?”

“We’ll have a bat.”

Before Nicholas realised that a random punter had run out onto the field to attend the toss, the man had scuttered off to place a bet before the toss outcome was known by the bookies, ever in search of an edge. That man? Findlay, of course.

Doyle Brunson – Lifelong poker pro

The other names on this list are legendary gamblers who bet on numerous sports and also chanced their hands at casino games along the way, but for Brunson it was almost always just about the poker.

Mind you, even though these days it’s mostly Texas Hold’em that catches the most attention among the poker community with that being the format that has the most televised matches and is most talked about on websites, TV channels, forums and social media, there are dozens of different types of poker (and some of which are no longer played much): Brunson played just about every last one of them at one stage or another.

That perhaps shouldn’t be that surprising. After all, this is a man who spent over six decades sat at poker tables from Mafia-run tables in backrooms at dangerous bars, to the final table at the World Series of Poker on numerous occasions and the glitziest and swankiest tables. Sometimes these games were organised just so that rich players of somewhat limited ability could say they sat down with the great man. Brunson carried on playing almost right up until his death in 2023, aged 89.

That he lived that long is something of a miracle in itself. In the early 60s a tumour was discovered on his neck that was operated on and never came back.

In one poker match in one of those dodgy backrooms a man was shot dead at the table he was playing at; on another day it could have been him.

At around the same time, a mobster called Tony ‘The Ant’ Spilotro- the inspiration for the Joe Pesci character in the movie Casino- threated to kill him if Brunson didn’t pay him 25% of any future winnings. Brunson ignored the bluff, telling him: “You can’t kill everyone.”

A similarly hair-raising story is that a player called Red Dodson died in front of Brunson at the table after losing a hand to him; it was the only possible hand that could have beaten him in a type of poker where the winner is the player with the lowest, rather than strongest, hand. “I felt bad, but that’s poker, and bad beats happen.” Doyle later said of the incident.

In 1978 he also released the first-ever mainstream book about playing and winning at poker called “Super/System” the first time a real pro revealed some of the game’s secrets and foolproof strategies.

In 2004 during the online poker boom he had his own poker website called “Doyle’s Room.” It gained huge popularity mostly due to his name being associated with it and the fact he played there himself and according to Brunson, he once received an offer for 235 million dollars for it. Thinking it was worth more than that, he turned it down. Shortly after, the federal government cracked down on poker websites in what was known as ‘Black Friday’ and he never got to cash in on it.

To list all the WSOP bracelets he won over the years, other big tournaments he won big at, or career prize earnings is both too time-consuming to do here and even then, not really what he was all about. This is a man from the old-school days who was among the first to turn the game mainstream and help fuel the worldwide obsession with it when it went online.

So instead, we’ll leave you with this tale. In 2003 his weight had become a major issue for him, both in terms of health and actually just being able to stand up at the table during games.

A bet was struck where he backed himself at odds of 10/1 to lose 100 pounds in two years.  He put down 100,000 dollars and would win 1 million if it came off. After a year and a half of little or no weight loss, a special diet all of a sudden worked for him and the pounds started falling off.

With two months to go and 98 pounds shed, he accepted an early payout of 980,000 US Dollars. Seeing as his friends were already there to pay up, they decided to play some poker.

Brunson, having worked so hard to lose all that weight for the past two years, lost the lot. But this was a rare occurrence for a man who for such a long time wasn’t just another poker player; he almost was poker.

The Earl of Sandwich- The pioneer

John Montagu (1718-1792) was a nobleman who was a British statesman and held plenty of extremely important military and political offices throughout his lifetime.

However, it’s perhaps what he invented that will remain as his long-lasting legacy.

And the invention was a direct result of the fact that he was an extremely keen gambler.

During lengthy card-playing sessions he was averse to leaving the table for meals so used to tell his servants to prepare him slices of meat in between two pieces of bread so he could eat, talk and carry on playing without interruption.

On noticing his newly developed dish, other gamblers would ask their own servants to have ‘the same as Sandwich’ and it became known as such. So keen was the Earl himself on his creation that he’s believed to have developed plenty of other variations, including egg sandwiches and even grilled cheese sandwiches.

Unlike some of the other gamblers on this list, it’s not for obscenely big or outrageous bets that he’s best known for but rather a reluctance to leave the gambling table.

In the process, one of the world’s most popular snacks was born. An extremely popular chain of sandwich restaurants in the USA, somewhat similar to Subway, was named after him.

John Daly – Wild Thing

Here at Punters Pub, we very often emphasise the importance of responsible gambling.  From setting yourself a budget, to only betting what you can afford to lose, setting yourself deposit limits and if necessary, self-excluding or seeking help to deal with problem gambling.

One suspects US golfer John Daly never took it particularly seriously and so we’ll round things off with a cautionary tale of why responsible gambling is so important.

Born in 1966 Daly was known as a brash, outspoken golfer nicknamed ‘Long John’ for his huge distance off the tee. He won 19 tournaments in numerous different countries and two Majors: the 1991 PGA Championship and the 1995 Open Championship.

But he was also known as ‘Wild Thing’ and this nickname was to prove his downfall.

A heavy smoker, big drinker, Diet Coke addict, taker of recreational drugs and a man who was overweight for most of his life, he was also a massive gambler. If you scroll up to the top where we talk about Kerry Packer, you’ll see that he’s mentioned in one of the stories about the late Australian.

In 2006 he revealed that he lost between 50 and 60 million US Dollars gambling, including on American Football but primarily at casino tables, especially blackjack. He admitted to regularly blackjack for over 200,000 dollars a hand.

In 2005 just hours after losing a play-off to Tiger Woods at the WGC American Express Championship (but winning around 750,000 US Dollars in prize money for his runner-up spot) he headed to the Wynn Casino where he proceeded to lose twice the amount he’d just pocketed in prize money, most of it on a slot machine.

So, it’s not hard to imagine that for the best part of two decades, a big part of all the money he was winning due to his talent on the golf course was invariably being lost at casino tables all around the USA.

He makes this list for the extent of his losses but that’s certainly not what he wishes he was best remember for.

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