Top 25 most outrageous gambles

We’ve sifted through the annals of history to bring you our top 25 most outrageous gambles of all time.

Never mind the slings and arrows of outrageous fortune, here at InsideEdge we’re more interested in the fortunes made from outrageous gambles. The past is littered with the forgotten stories of bookies, politicians, card-sharps, money men, crooks, inventors, singers, businessmen and soldiers who took incredible gambles that never paid off. But history is written by, for and mostly about the winners.

So we asked all of InsideEdge’s many contributors to trawl the centuries for history’s most extravagantly clever, most disgustingly daring, most downright lucky punts to have offended gambling decency, and sifted through hundreds to produce our top 25.

We bring you our top 25, in no particular order. They’re an eclectic bunch, but we hope they prove that history can, if not educate us as gamblers, at the very least entertain and sometimes amaze us.


Speaking of villains, perhaps the biggest of them all, Mr Big, AR, the Big Bankroll, aka Arnold Rothstein, actually didn’t like to gamble that much. This may seem a bit odd for a man who had been a professional gambler since childhood, but not when you remember that he did prefer to get the odds in his favour by fixing things. He had jockeys, owners, stable hands, trainers and track owners in his payroll, and he owned dubious games in illegal casinos in New York in the Depression. However, the biggest coup of his life was finding out that eight members of the Chicago White Sox baseball team, which had just qualified for the final of the 1919 World Series, were disenchanted with the team’s mean millionaire owner.

Naturally, he bunged them to throw the series. They duly obliged and he won $500,000. Baseball was the loser.

Not much of a gamble, perhaps, but certainly outrageous. He won a similar sum of money on the 1928 Presidential election. History spared him from a fixing charge because, luckily, he was murdered the day before the result.

TIP: If you’re going to become one of the biggest gangsters the world has seen, do it with wit and style/.


In the days when cricket was still a game played by gentlemen who got paid roughly bugger all yet would still rather win than take a bung, Dennis Lillee and Rod Marsh of Australia’s 1981 Ashes team were a bit naughty. Anyone who knew the pair would have told you they’d rather die than lose, but neither could resist the bookies’ lure of 500/1 on England to get off the Headingly rack to which they’d been strapped.

They couldn’t have known the betting scandals to come and would have been horrified to see one Ian Botham repeatedly hooking Lillee into the stands off his eyebrows, finding his way back to the pavilion some 149 runs better off. The several grand they must’ve won must have seemed more pleasurable than facing Bob Willis, who was famously ‘steaming in from the Kirkstall Lane End’ (R Benaud) at warp speed, taking eight wickets and bowling Australia out for a little over 100. The Aussie pair had to give up the winnings and apologise when some spoilsport grassed them up.

TIP: If you can influence a set of circumstances, why not try to make money from it?.


InsideEdge columnist Nick Leeson was the goldenballs of the banking world when he made almost $30 million in a single year for Barings Bank in Singapore. However, this success went to his head and Leeson believed he could get away with anything.

As his reputation soared, he set up a special account that only he controlled. This account concealed larger and larger losses. However, due to the bank’s 232-year history and Leeson’s iron-clad respectability, no one bothered to look into his increasingly wild dealings.

Towards the end of 1994 and 1995, his losses threatened to overwhelm him, so he made a massive bet on the Japanese stock market by purchasing futures pegged to the Nikkei 225. A bit like betting on more than 2.5 goals in a football match, Leeson bet the Nikkei would go up.

As far as market criteria went, this was the right thing to do. Unfortunately for Leeson, he hadn’t factored in acts of God, and a huge earthquake in Kobe sent the Nikkei plummeting. Leeson knew it was shit or bust, so he massively increased his investment in a vain bid to influence the market. The rest is history. On 23 February 1995, Leeson fled Singapore. He was finally arrested in Germany and sentenced to six-and-a-half years in jail, and the world-famous Barings Bank went under.

TIP: Don’t push your luck when you’re winning, make sure you hedge and always check seismic studies for the threat of earthquakes.


Villains gamble with their livelihoods all the time, but if you’re going to do that, you might as well do it with some style, pluck, and good old-fashioned British chutzpah. Scotsman Arthur Ferguson, tired of treading cheap boards as a distinctly mediocre actor, suddenly found his starring role when in a six-week period in 1925 he sold Big Ben for a grand, Buckingham Palace for two grand – twice! – and Nelson’s Column for £6,000 to American tourists.

Encouraged by his successes, Ferguson emigrated to the US, where he nearly managed to rent the White House to a Texan cattle baron for $100,000 a year.

His luck came to an end when he accidentally appeared in a photograph of the Statue of Liberty when he had nearly disposed of the good lady to an Australian. He was nicked and got five years. Considering it merely a career break, the ever-creative Ferguson died a rich man in California in 1938.

TIP: Gullibility is a marvellous quality that gamblers should feel free to exploit.


In March 2000, the UK Government launched the first 3G spectrum licence auction. There were 13 bidders for five licences. As bids soared beyond expectations, it became clear that the UK Government would receive more money than it could possibly have imagined. By the time NTL Mobile pulled out in the 149th round, the combined bids of the five successful companies came to the tidy sum of £22.5 billion. Those ‘winning’ companies are now known as Vodafone, Orange, 3, T-Mobile and O2, and it’s only in the last six months that 3G services were launched.

TIP: Try to think five years in advance and don’t lose your head when everyone around you have lost theirs.


Michael Jackson was only five years old when he became a singer with the Jackson Five, a family troupe of singers that played the local bars and clubs of Gary, Indiana. In 1968, Bobby Taylor and the Vancouvers discovered the Jackson Five and from there they got an audition with Berry Gordy of Motown Records, who promptly signed them up.

Getting a deal with Motown was Nirvana for bands such as the Jackson Five, and the first four sincles I Want You Back, ABC, The Love You Saved and I’ll Be There all went to No.1 in the US. Success followed success: the Jackson Five recorded 14 albums and Michael Jackson recorded four solo albums with Motown.

There seemed to be no end to the great relationship, but Jackson was convinced Motown were holding him back creatively, so he persuaded the family to make the monumental decision to leave Motown and sign for Epic Records. At the time, the music industry saw it as the end for the band, as Motown owned the Jackson Five name and they had to change their name to The Jacksons.

Jackson, however, had other ideas. He engaged Quincy Jones to work with him at Epic on Off the Wall, his first solo album as an adult. The album went on to sell 20 million and paved the way for Thriller, still the world’s best-selling album, with more than 50 million sold.

TIP: Concentrate on music for the kids, not the kids themselves.


On 2 July 2003, the previously unknown Russian billionaire Roman Abramovich bought Chelsea Football Club for £140 million. The deal was unexpected because the club was close to going out of business with debts reaching £80 million.

Chelsea had invested heavily in expensive players with little success. Over the next 18 months, the club spent a staggering £220 million on new players such as Didier Drogba, Joe Cole and Claude Makelele. This meant the club lost £88 million in the year ending 2004 as the annual payroll went up to £115 million. The club had also taken a risk in appointing young Portuguese manager Jose Mourinho.

But by the end of the 2004-2005 season, Chelsea had won the Premiership for the first time in 50 years. They had also won the Carling Cup and were narrowly beaten by Liverpool in the Champions League semi-final. Mourinho was acclaimed as one of the world’s best coaches. The club’s objective is to break even by season 2009-2010 and insists the wild spending is over.

TIP: Reach for the stars but don’t blow £16 million on coke-addled Romanians called Adrian Mutu.


Texan horse trader and professional gambler William Lee Bergstrom became known as the ‘Suitcase Man’ when he turned up at Binion’s Gambling Hall and Hotel in Las Vegas. It was 1980 and the casino guaranteed to match any bet as long as it was that punter’s first bet. Bergstrom had wanted to wager $1 million in a single beat at craps, but apologised to the casino and said he only had $777,000. Would they match it?

Bergstrom was obviously a confident man. He had two suitcases with him; one held the money, the other was for his winnings.

Binion’s matched the bet and Bergstrom wagered all at once on the don’t pass line at craps. Two rolls later, he packed his money away in both suitcases and left.

For someone who had wanted to bet $1 million, Bergstrom’s following actions were a little weird. Instead of banking $554,000 of his winnings and punting the million he wanted to, Bergstrom then punted $590,000 and won; $190,000 and won; and, finally, $90,000… and won.

However, Bergstrom eventually went for the million bet about four years later. Naturally, he lost and there are several stories about what happened next. Depending who you talk to, he headed for his room at the Tropicana and blew his head off, leapt out of the top floor window at the Tropicana or died from an overdose.

TIP: Go to Vegas and have the front to walk around carrying a bag for your winnings, but only do it once and don’t stay at the Tropicana – go to the Bellagio instead.


US businessman Malcolm Glazer has taken control of Manchester United for a fortune. Not only was his £800 million takeover a huge risk, but he also stands to lose his shirt and much more besides if the team fails to deliver success on the pitch next season.

High on his success of buying the Tampa Bay Buccaneers in the US’s Nfland their subsequent Super Bowl victory, Glazer’s interest in United began in March 2003 when he bought a 2.9% stake in the club. Over the next 18 months, he slowly increased his stake to 28.1%. He made his first failed bid for the club in October 2004.

He then incurred the wrath of Manchester United’s shareholders by mounting two further bids. Undeterred by death threats and increased militancy from sectors of Manchester United’s supporters, Glazer continued his quest.

Glazer is not only gambling with the club’s future with his capital structure, which means huge debts and increased season ticket costs, but he threatens to make himself unpopular with fans of other Premiership clubs if he destroys the collective bargaining for TV rights that has worked well so far. Clearly the man has the skin of a rhino.

TIP: Don’t come to England from America and think you can take over one of its most glamorous clubs without a fight.


Self-styled philanthropist and patron of the arts George Soros was the man ‘who broke the Bank of England’ during the dark days of September 1992 when Britain was forced out of the Exchange Rate Mechanism (ERM).

Soros was born in Hungary, but emigrated to Britain when he was 17 after the end of the Second World War. He studied philosophy at the London School of Economics with Karl Popper, whose views on the need for tolerant and market-driven societies as a precursor of economic growth he adopted.

Soros’ financial career began in London before he moved to Wall Street in 1956. He set up the Quantum fund as one of the world’s first hedge funds that invested in risky, but potential, global deals.

By the early 1980s, Soros had a personal fortune of £16.5 million, and the stage was already set for the most famous deal of his life. Soros believed the pound had to be devalued because it had entered the ERM at too high a rate. He spent the next few months building up a position from which he would profit from devaluation. He borrowed £6.5 billion of sterling and converted it into a mixture of French francs and Deutschmarks. On Black Wednesday, Soros’ bet paid off. In the following days, he unwound his positions, paying back his original borrowings and ending up with a profit of around £1 billion. Not bad for a week’s work.

TIP: Stay in bed four days of the week and only venture out on Wednesdays, and never carry sterling.


Ex-waiter Archie Karas was a Greek immigrant to the US who was skint and borrowed $10,000 from a friend to play poker at the legendary Binion’s Horseshoe casino in Las Vegas.

Karas went on to defeat 15 of the world’s greatest poker players in head-to-head competition. These included world champions Stu Ungar, Johnny Chan and Chip Reese. When he had exhausted poker competitions, he headed over to the craps tables and kept on winning.

At one point, Karas had all of the Horseshoe’s $5,000 chips (more than $11 million) and when his run was over, he was able to pay back his $10,000 loan and still have $17 million in his pocket.

TIP: If you feel lucky, get yourself a bankroll and grab some action.


In the mid 1980s, it seemed that British entrepreneur Sir Clive Sinclair could do no wrong. His technical genius and seemingly spot-on business acumen had seen him successfully sell the first pocket calculator, the first pocket television and the ZX Spectrum, the best-selling computer of its time.

However, in 1985, the wheels fell off Sinclair’s empire when he gambled on the C5, the ‘world’s first commercial electric car’. Sinclair believed the C5 would be a revolutionary advance in personal transport that would finally replace the car in cities.

At only £399, the C5 was a fraction of the price of a conventional car, but it wasn’t long before it became the subject of derision. Built by Hoover, a company better known for vacuum cleaners, it wasn’t long before unflattering comparisons were made between the two product lines. The C5 was no more than a glorified tricycle powered by an electric battery and pedals. The vehicle could only reach speeds of 15mph and its battery could only handle a limited range of ten miles. It’s size also meant that it was dangerous in heavy traffic.

Only 17,500 were ever sold, production ceased after a couple of months and losses of £7 million meant Sinclair had to sell the company to Amstrad at a knockdown price. However, C5s are now highly sought-after collector’s items and now sell for up to £900.

TIP: Don’t make ‘revolutionary’ vehicles if they can’t go far, can’t go very fast and can’t be seen by other cars.


Legendary three-time World Series of Poker main event winner Stu Ungar’s story was one of extraordinary pathos that ended with his death in a Las Vegas hotel in 1998 when still in his forties. A huge 20-year cocaine habit added to a daily intake of painkillers and other drugs triggered a heart condition that finished him off.

But in his early days, Ungar’s heart was stronger than anyone’s around him – and his memory was even better. In Vegas more than 20 years earlier he bet all-comers $10,000 he could memorise and recall two decks of cards in a six-deck pack.

There were no takers until Bob Stupak, a former owner of Vegas World and designer of the Stratosphere Tower offered Ungar $100,000 against $10,000 to count down three decks. Ungar did it without missing a card.

Unfortunately for Ungar, about whom it was said ‘the kid must have action’, his future gambling wasn’t always so successful. After one of his WSOP wins, he lost $1.5 million in a weekend gambling on sports and even lost $80,000 the first time he ever played golf. Ungar didn’t even make it to the first tee and lost the 80 grand on the putting green.

TIP: Don’t go to Vegas, get whacked off your head on coke for two decades and expect to come up smiling.


Larger-than-life Australian media tycoon Kerry Packer has lived a life straight out of the pages of a Marvel comic book, but there’s one story for which he’ll always be remembered. Uncomfortable with the attention a stranger was receiving from a waitress at a casino, Packer turned to the stranger and asked why his presence was causing such a stir. The Texan gentleman replied that he was in the oil business and worth $100 million. ‘Toss yer for it,’ was Packer’s historic reply. The oilman walked away.

Packer obviously liked waitresses, too. He once asked a waitress why she wasn’t at home with her husband and kids. When she replied that she had a mortgage to pay, Packer promptly paid it off for her. What a guy.

TIP: If you’ve got it, flaunt it.


The Hermits of Salisbury Plain were a quintet of professional gamblers who, in relative terms, pulled off some of the biggest bets of all time at the start of the twentieth century.

Led by Old Etonian City financier Percy Cunliffe and aided by Irish stud-owner Wilfred Purefoy, the group ran up a string of betting coups from a team of horses trained at the secretive Druid’s Lodge stables on Salisbury Plain. The place was so shrouded in mystery that even the stable lads’ mail was opened to stop information being passed on to the wider betting public.

When the Hermits’ horse, Hackler’s Pride, who was trained by Jack Fallon, won the 1903 Cambridgeshire, the group were thought to have netted £250,000, which is about £10 million in today’s money! In the same season, another of their horses, Ypsilanti, was backed in from 25/1 to 7/2 favourite for the Great Jubilee at Kempton Park, netting £4 million in the equivalent of today’s cash.

TIP: If you’re planning a racecourse coup, don’t tell anyone about it.


The 1836 St Leger proved extremely profitable for Lord George Bentinck, one of horse racing’s great reformers and also a fearless punter to boot. Back in those days, horses had to be walked to whichever racecourse they were due to compete in. So when bookmakers discovered that Bentinck’s fancied mount, Elis, was still based down in Goodwood just a few days before the 1836 St Leger run at Doncaster, the odds on his charge duly lengthened.

However, what the bookies hadn’t reckoned on was Bentinck devising the first horse transporter. A specially constructed carriage enabled Elis to be pulled to Town Moor by other horses in time for the race. He was sent off as the 7/2 second favourite and hosed home, making Lord George a tidy sum in the process.

TIP: Always keep one step ahead of technology.


On 1 August 1898, The Sportsman newspaper printed a racecard with runners and riders for that day’s jumps meeting at Trodmore Hunt in Cornwall.

The following day, the paper ran the results of the races run at the meeting. A day after that, rival publication Sporting Life duly followed suit by providing readers with all details of the winners from the Trodmore contests.

Major bets on those races had been placed with several bookmakers in the London area and several of these layers were happy to pay out on the results as they appeared in The Sportsman.

Nothing terribly eye catching in all this, of course, until you discover that Trodmore races was all a sham! The meeting never took place, but instead was the concoction of a group of swindlers who pulled off a major coup.

Somehow, members of the Trodmore gang (their real identity was never discovered) had managed to persuade The Sportsman editor to include the Trodmore card in his paper. The gang then passed on results by wire that were subsequently included in the publication.

The conspirators got away with thousands of pounds in today’s terms. And if it hadn’t been for a misprint in Sporting Life’s version of results, would have made off with even more.

TIP: Ignorance is bliss, especially for punters. If people are stupid, you owe it to yourself to take their money.


When floodlights were cut at a spate of English football matches in the 1990s, foul play was suspected. Rightly so – an Asian betting syndicate was behind the blackouts.

Asian bookmakers pay out on the score as it stands if a game is abandoned, so the motive was obvious. The gang used a remote control to cut the floodlights when the game was in their favour. Two games disrupted in 1997 are thought to have netted the gang up to £60 million in a betting coup. The scam was only uncovered when Malaysians Chee Kew Ong and Eng Hwa Lim were caught red-handed at Charlton Athletic’s ground. Police found enough electrical equipment to create problems at another eight matches.

TIP: If an electrician tells you he knows a sure-fire way of making money, walk away.


One lucky punter from Newport, South Wales went into his local Ladbrokes on 30 December 1989 and decided to place a £30 accumulator on a series of events happening before the end of the Millennium.

The 40-year-old night-shift worker took the odds available at the time of 4/1 on Cliff Richard being knighted, pop act U2 remaining as a group at 3/1, Eastenders still being shown on the BBC as a weekly soap opera at 5/1, and that Australian soaps Neighbours and Home and Away would still be going strong and on British television well into the year 2000 at odds of 5/1 and 8/1 respectively.

Then, a couple of days into January 2000, the same man turned up in a Newport betting shop with a crumpled betting slip asking to be paid £194,400, but as Ed Nicholson, PR manager at Ladbrokes at the time explains, it took a few days for him to get the cheque! ‘No one had ever mentioned the bet to anyone at head office. Every check possible was taken to ensure it was a bona fide wager, but once everyone was sure the bet was genuine, the firm paid.’

The £194,400 payout remains to this day the largest novelty bet payout in history, while the accumulative odds of 6,479/1 may never be beaten!

TIP: If you have a hunch that something will happen, back it.


Everyone knows accumulators are a waste of money, but don’t tell Mick Gibbs that. He netted the most outrageous football accumulator of all time in 2001, when his 15-fold acca netted him a £500,000 jackpot.

The outcome of the multi-layer bet rested on Valencia versus Bayern Munich in the Champions League. The game went to penalties. ‘I was pacing and praying,’ said Gibbs. ‘I was shaking like a leaf.’

Bayern triumphed and Gibbs celebrated. As if that wasn’t enough, he had hit the acca jackpot two years earlier, when he won £157,000 from a £2.50 wager. The bet as clinched when Manchester United staged a dramatic finale comeback to beat Bayern Munich in the Champions League final. Some guys have all the luck.

TIP: Sometimes the longest of shots will come in for you.


It’s 29 September 2001 and half time at White Hart Lane. Spurs are leading Manchester United 3-0 and, in a bid to impress his girlfriend, one Tottenham fan stakes his entire mortgage on Spurs to win the game. United go on to win 5-3 and the punter goes home to an empty house (and an empty bed). For charity’s sake, we won’t mention the poor chap’s name.

TIP: It ‘s not over ’til the fat lady sings – especially when Spurs are playing.


Thinking Kicking King was lame, his trainer, Pat Taafe, put the horse on a course of antibiotics two weeks before the Gold Cup. Great news for him when the horse won, but not so good for bettors at Betfair who had laid £47 at 999/1 when Taafe said the horse wouldn’t be heading to the Cotswolds.

TIP: If a top trainer says his horse is ill, pile in at huge odds on Betfair.


The 8/11 shot Family Business was brought down in a novice chase at Southwell. Jockey Tony McCoy was headed back to the stables as one Australian Betfair customer punted $AUS11 (about a fiver) on the horse to win at 1,000/1. The four remaining runners all fell, McCoy remounted Family Business, who went on to complete the course and win the race.

TIP: Never underestimate the tenacity of an ambitious champion jockey.


On 24 August 1875, Captain Matthew Webb became the first man to swim the English Channel. But while he was good at swimming, he was useless at making money. He was forced to go to the US to swim races for money against Native American swimmers, usually winning them but wasting the money on hare-brained schemes. Finally, Webb staked his life against $10,000 to swim across the whirlpool below Niagara Falls. Ten thousand spectators turned up to see his attempt, but halfway across he threw up his arms and was drawn under to his death. His final words were: ‘If I die, they will do something for my wife.’ Brave, but silly.

TIP: Never show off.


Ashley Revell sold everything he owned, including his name, for £10,000 to Blue Square, raised more than $150,000 and headed to Vegas. He lobbed the whole lot on red in a game of roulette at the Plaza casino and the gamble was landed when the ball fell into the red number 7 slot.

You may not be surprised to learn that he is still quite a gambler. However, as he won the bet, he is still in possession of a girlfriend and has even bought a few things to replace all the things he had to flog to raise his stake.

TIP: Develop elephantine cohones, take them to Vegas and get stuck in.

Pin It

Comments are closed.