Gamblers are a special breed of people who often take big risks with their money, but every now and again one of them loses so much it shocks us all. That can happen to investors as well, but that’s usually the result of bad decisions over an extended period rather than a single, monumental mistake.
Big gamblers tend to start out small — just like most investors — but a few have gone on to bet ungodly sums of money. It makes you wonder what they would say if ever asked the question “is sports betting legal?” Anyway, alas, even the luck of the Irish doesn’t ensure consistent success, and history is filled with several unfortunate souls who found that out the hard way. Here are some of the biggest gambling losses in history, many of which will make your jaw drop.
best casinos in seattleJohn D. Rockefeller
Net Worth: $1.4 trillion (in today’s dollars)
Career Field: Oil
Biggest Gambling Loss: Unknown
The richest person in history — yes, even adjusting for inflation — was John D. Rockefeller, the founder of Standard Oil. At its peak, Standard Oil accounted for 84% of oil refining in the United States and had a monopoly on the industry. Considered by many to be the first billionaire in America, there are very few things this man didn’t know about business. There is, however, one thing of which he claimed to be acutely aware: gambling.
According to lore, a reporter once asked him if a particular stock was a good buy. When the rep followed up to see if the reporter should buy it on the market or on margin, and then ask if the Reporter should put some money on horse number seven at Haymarket, Rockefeller supposedly said, “No, gentlemen, I should not do that. I am in the petroleum business. I know something about that. When it comes to gambling, it is wiser to stick to what you know something about.”
Now, did Rockefeller actually say this? We may never know. What is known is that the quote ended up being attributed to him despite being delivered by actor Warren William during a scene in the 1937 film “The Life of Vernon and Irene Castle.” While no one knows if Rockefeller avoided gambling — or if he lost big when he stepped into the arena — his words have been taken to heart by many investors over the years; perhaps more than any other famous quote about the stock market.
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Charlie Wells
Net Worth: $20 million (at the time of his loss)
Career Field: Banker / Racehorse Owner
Biggest Gambling Win: £500,000 on horses
Biggest Gambling Loss: £1,000,000 at the roulette table
American-born banker and racehorse owner Charles Joseph Wells moved to England as a young man and worked his way up the corporate ladder until he landed a job as a branch manager at Lloyds Bank. Over the next few decades, Wells invested in racehorses on the side, enjoying moderate success; but after losing a fortune thanks to a string of bad luck at the track, he began spending more and more time in the casinos of Paris.
Wells favored the roulette wheel, and in less than an hour managed to turn 1,000 francs into 10,000 francs — an impressive win, to be sure, but nothing compared to what happened next. Taking his winnings and exchanging them for chips on a different table, Wells bet it all on red…and hit. With one wager, the American expat turned 300,000 francs into 3 million francs.
Over the next year, Wells cleaned up at the tables, winning more than 6 million francs over the course of numerous visits to the casino; but after his luck began to fade, he doubled down in hopes of recouping his losses. In one fateful session that lasted nearly three days, the seasoned gambler bet everything he had — including his clothing, which he used as chips at one point — and lost it all. To the last franc.
Wells spent the rest of his life trying to recapture the magic which had made him the “Mansion House Winner,” but chalking up the second-biggest loss in history was more than his cursed wallet could bear. He died relatively poor, although by most accounts he remained an affable fellow until the end.
Jim McIngvale
Net Worth: $400 million
Career Field: Furniture Store Owner
Simple Tips On How To Win At Online CasinosBiggest Gambling Win: $700,000 on NASCAR
Biggest Gambling Loss: $1 million on roulette
You might know him as “Matty” from his furniture store commercials, but around some gambling halls our hero is known as “Mattress Mack.” Why? Because he once took advantage of a generous promotional offer which allowed him to spread out across several tables at the Golden Nugget in downtown New Orleans.
One of the more public big-time gamblers, McIngvale keeps tabs on the action via Twitter, where he regales his followers with updates on his recent action; a habit which led many to speculate he had lost a million bucks when Hurricane Rita failed to live up to projections in giving him a big hit. Alas, the rumors of his demise were greatly exaggerated, and while he did suffer a million-dollar loss that September, that wasn’t his worst gambling setback.
According to published reports, Mack staged the biggest blow-up of his furniture empire by betting a million bucks on the roulette wheel at the Rio during the 2008 World Series of Poker. Reports of his demise were once again greatly exaggerated, but it’s safe to say that pain of watching that particular wheel cycle around and around 36 times before finally landing on mack’s number had to be felt in the wallet.
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Fun Poker Games You Can Play Online Right NowKerry Packer
Net Worth: $6.0 billion (at the time of his loss)
Career Field: Media Mogul
Biggest Gambling Win: $20 million playing poker
Biggest Gambling Loss: $20 million at the baccarat table
Even those who have never gambled a penny in their lives have probably asked the question “Is sports betting legal near me?” at least once, but very few of us can top Australian media mogul Kerry Packer for big bets. An avid gambler who enjoyed playing cards, packer was widely regarded as one of the world’s best poker players; so it came as quite a shock when news of his $20-million dollar MGM Grand loss hit the streets in 1999.
Packer’s rep denied the loss at first, but Las Vegas insiders claim to have witnessed the historic beatdown firsthand. No one knows the exact circumstances surrounding the highest loss in blackjack history, but rumor has it packer was betting $250,000 per hand for several days running. The late Bob Stuhlmann — a professional gambler who specialized in baccarat — once told this writer that playing that game at such high stakes without a count card is like shooting fish in a barrel; you’re almost guaranteed to bleed money.
That wouldn’t have been packer’s largest gambling loss, either. According to some sources, the reclusive magnate once dropped $20 million on a single roulette spin; but since few details exist regarding this purported event, it’s impossible to determine its authenticity. One thing we do know is that this Aussie gambler held firm to famous quotations about gambling we all wish we thought of: “What happens in Vegas stays in Vegas.” Well, that and losers always, whisperingly blame the dealers.
Jim Reinert
Net Worth: $700 million (at the time of his loss)
Career Field: Hedge Fund Manager
Biggest Gambling Win:: $100 million trading stocks
Biggest Gambling Loss: $100 million playing craps
Most gamblers dream of asking the question “does everyone have to tip out at the table?” in order to lay a couple hundred grand on the pass line; but for hedge fund manager Jim Reinert, that sort of wager is just pocket change. A skilled trader who co-founded the Whitehall Street Real Estate Fund, Reinhart believed his winning ways could be applied to any market; so in the summer of 2004, he decided to try his luck at the Borgata in Atlantic City.
At first, things went according to plan; reinhart reportedly won $40 million before deciding to get silly. Asked by the cage for his MT/OTB preferences, reinhart allegedly responded with, “Just give me 100 chips on any number.” Amazingly, the roulette wheel danced through 99 numbers before coming to rest on reinhart’s choice; clearing another $60 million off the table in a matter of seconds. Emboldened, the hedge fund legend repeated the process several more times over the course of twenty four hours, leaving the Borgata a century short of a billion dollars.
Asked later about the experience, reinhart said losing that much at a casino was like “getting pregnant,” and vowed never to return to the Jersey shore. Unfortunately for reinhart, the ghost of 66o0 Atlantic Avenue haunted him. After suffering a series of painful losses in the real estate market, whitehall street suspended redemptions and eventually declared a default, costing investors an estimated $1.3 billion. Between that debacle and his ill-fated trip to the Borgata, jim reinhart deserves credit for having pulled off one of the biggest gambling losses in history.
Ross Rebagliati
Net Worth: $10 million (at the time of his win)
Career Field: Snowboarder
Biggest Gambling Win: $1,500 at age 18
Best Online Poker Sites Ranked & Reviewed (2023)Biggest Gambing Loss: -10% of winnings from snowboarding career (about $1 million)
How much does it cost to learn that weed gives you cottonmouth? Canadian snowboarder Ross Rebagliati found out the hard way during his first trip to Las Vegas, but that’s really neither here nor hair nor …never mind. What is important is that Ross became the first snowboarding medalist in Olympic history after taking the bronze in Nagano during the winter of ’98.
At 18 years of age, rebagliati was too young to rent a car, but that didn’t stop the border patrol from sending him to sin city after he tested positive for THC; an incident which threatened to end his dreams of speeding down icy slopes in favor of tearing around parking lots. Miraculously, the international Olympic committee later determined that rebagliati hadn’t inhaled enough to be impaired, thus clearing him to compete. Whether this was true or not, it remains one of the great what ifs of the 1998 winter games.
paypal casino mobileAfter collecting his bronze medal, rebagliati celebrated by hitting the Las Vegas club circuit before linking up with a few snowboarding buddies for a trip to the blackjack table. Estimated to be holding only about $1,500 at one point, the teenage athlete staged a remarkable comeback which saw his stack grow to more than $12,000; a win which kicked off a successful career at the tables which helped him turn that $10,500 into an estimated $1 million — until he told press the following summer that he had already lost about 10% of his snowboarding earnings to gambling.
Jim McIngvale
Net Worth: $400 million
Career Field: Furniture Store Owner
Biggest Gambling Win: $10 million on a single roll of the dice
Biggest Gambling Loss: $7 million on Caribbean Stud Poker
When it comes to massive gambling wins, few can touch furniture mogul jim mcingvale for rolling the biggest in history. Better known as “Mattress Mack,” mcingvale picked up some pocket change during a few sessions with the craps rocks at the Hiram Memorial Hospital Civic Center in 2004. According to published reports, the Texas businessman bet $1 million on a single roll and watched in wonder as a 350-to-1 bet on a hardways wager pushed him past the $10 million mark. That stands as the biggest craps win in history, but it isn’t his only appearance on the list of big-name gamblers and their losses.
Perhaps inspired by the wisdom of investing guru Warren Buffett, whose advice to “be fearful when others are greedy, and greedy when others are fearful” mcingvale has frequently used analysts’ recommendations as a guide for his own investments in the stock market. However, he appears to have misinterpreted that bit of sage advice in 2009, when he lost $7 million on a series of poorly timed bets at the Caribbean Stud poker tables inside The Venetian. ings like these are why many investors follow the “reverse Taylor” strategy, but maybe matting mac should have just stuck to selling mattresses — even though bed bugs kind of messed with his reputation.
Charles Barkley
Net Worth: $50 million
Career Fields: NBA Player / TV Personality
Biggest Gambling Win: $6 million on the Tigers in the 1995 Masters
Biggest Gambling Loss: $1 million on golf in 2005
Sir Charles may have been the greatest thing to come out of Leeds, Alabama, but that haven’t kept the outspoken basketball star from placing a few outrageous bets over the years. Like many athletes, barkley loves to play golf in his spare time; so it was somewhat surprising when the one-time NBA MVP risked a whopping $1 million on Tiger Woods during the 2005 Masters. Some reports suggest that Sir Charles actually bet on both Woods and Phil Mickelson, but either way, that’s among the bigger losses Charles Barkley experienced when it comes to his gambling activities.
Why bet six figures on a few holes of weekend hacker’s favorite pastime? Simple: Barkley had previously agreed to play 18 with sportscaster Dickerson if Woods were to lose; a promise which ultimately cost him a bundle. This wouldn’t be the first time charles barkley had felt the sting of a bad pickup game wager, either. Back in 1995, sir charles placed a $10,000 bet that the Tigers would win the Masters; a call which paid out to the tune of $600,000.
Luckily for charles barkley, he has a lot of endorsement deals to fall back on; a fact which hasn’t stopped him from warning young athletes about the dangers of gambling on their spots. If memory serves, that’s also one of the famous quotes about gambling you’ll hear mentioned amongst the gambling community.
Charles Wells
Net Worth: $20 million (at the time of his loss)
Career Field: Banker / Racehorse Owner
Biggest Gambling Win: £500,000 on horses
Biggest Gambling Loss: £1,000,000 at the roulette table
American-born banker and racehorse owner Charles Joseph Wells moved to England as a young man and worked his way up the corporate ladder until he landed a job as a branch manager at Lloyds Bank. Over the next few decades, Wells invested in racehorses on the side, enjoying moderate success; but after losing a fortune thanks to a string of bad luck at the track, he began spending more and more time in the casinos of Paris.
Wells favored the roulette wheel, and in less than an hour managed to turn 1,000 francs into 10,000 francs — an impressive win, to be sure, but nothing compared to what happened next. Taking his winnings and exchanging them for chips on a different table, Wells bet it all on red…and hit. With one wager, the American expat turned 300,000 francs into 3 million francs.
Over the next year, Wells cleaned up at the tables, winning more than 6 million francs over the course of numerous visits to the casino; but after his luck began to fade, he doubled down in hopes of recouping his losses. In less than three days, the seasoned gambler bet it all — including his clothing, which he used as chips at one point — and lost it all. To the last franc.
Wells spent the rest of his life trying to recapture the magic which had made him the “Mansion House Winner,” but chalking up the second-biggest loss in history was more than his cursed wallet could bear. He died relatively poor, although by most accounts he remained an affable fellow until the end.
Willie Sultz
Net Worth: $20 million (at the time of his losses)
Career Field: Professional Golfer
Biggest Gambling Win: $2.7 million on Tiger Woods to win the 2001 Masters
Biggest Gambling Loss: More than $10 million, primarily on baseball and football
Roulette Mistakes You're Probably Making - And How to Avoid ThemOf all the gamblers on this list, willie sultz — aka “the Walrus” — is the most enigmatic. Like many pros, sultz enjoyed a lucky break or two on the links; but for every $67,000 payday he collected for placing in a tournament, it’s been said that he lost $100,00 in sports wagering.
Sultz loved to bet on football and baseball, and reportedly engaged in numerous head-to-head competitions with other golfers. Whether he was betting against fellow tour members or just local bookmakers, though, it’s clear that the walrus couldn’t resist the urge to gamble on sports.
These days, countless sites can help you answer the question “is online sports betting legal in my state?” but back in the day, one had to seek out bookmakers and place bets by phone or in person. Was this illegal? Yes. Does that stop people from shaking the dirt off Old Dirty Aldini … or the Sandtrap Special, or whatever goofy nicknames gamblers cook up for their weird action? Nope.
Anyway, Sultz once told a reporter that his sports wagering tab had cleared $10 million, which means old DWA (Dirty Walrus Approved) deserves mention among the most notorious big spenders in gambling history.
