Biggest Casino Wins

Every time a player spins the reels or is dealt a hand of cards you are dreaming of a big win, but it’s only the lucky few who have fulfilled their dreams by winning millions of dollars playing at casinos.

In this comprehensive guide to the biggest casino wins we are looking at the most money ever won at a casino in more detail, outlining exactly how these players were able to walk away with life-changing sums in their pockets.

• Biggest Casino Win in History: Kerry Packer – $40 million
• Most Money Ever Won at a Casino List

Biggest Casino Win in History: Kerry Packer – $40 million

Kerry Packer tops our list of the biggest casino wins ever, with his reported $40m in winnings at the MGM Grand Casino in Las Vegas back in 1997. The Australian media tycoon – considered one of Australia’s most powerful media proprietors of the 20th-century – died in 2005 but was an avid gambler involved in a number of land-based sites such as the Crown Casino in Melbourne.

It is claimed that he won up to $40m at the MGM by playing an astonishing six blackjack hands at the same time with stakes of up to $200,000 per hand. Packer’s notoriety at cleaning out casinos in Sin City and around the world meant lots were wary of letting him play as his high-roller action could leave them bankrupt, although Las Vegas revenue statistics suggest his big win boosted the popularity of the MGM Grand.

Stories from the night vary from source to source, but Packer is believed to have turned extremely generous after his landmark win, giving away large tips to the staff on duty that evening. Things were not straightforward for the Australian though as he is fabled for his mammoth wins and losses – two years later going on a three-week blackjack session at Crockford’s casino in London costing him ￡11m, thought to be the biggest loss in British gambling history at the time.

The flamboyant Packer was renowned for his sometimes volcanic temper and unhidden contempt for journalists who dared to question his activities. In a poker tournament held at the Stratosphere Casino, a Texan oil investor is said to have tried to get him to play a game of poker, baiting him by claiming to be worth $60m. In response to this Packer pulled a coin out and nonchalantly asked: “Heads or tails?” in reference to a $120m wager.

Before you could play roulette online, casino owners in south-east England confirmed that he lost ￡15m playing on four roulette tables on his own at a major London casino in the late-1990s, while former PGA Tour golfer John Daily said he once closed down the Desert Inn Casino in Vegas after winning $52m and insisting that they pay him out in cash after the casino insisted upon him paying them in cash the day before when he lost $8m.

But for a man whose personal worth Australia’s Business Review Weekly magazine once estimated at $3 billion, these were just small lumps of change. The Ritz Hotel in London even had their own room for Packer where he was able to play blackjack hands with a minimum wager of ￡10,000, once losing ￡19m in the room.

Most Money Ever Won at a Casino List

Some of these may have been topped since playing slots online in New Jersey and other states become legal, but still constitute the money money ever won at land-based casinos.

Josh Ford – $39.7 million

Our next biggest casino win in history was a software engineer from Los Angeles who made a cool $39.7m betting on basketball. In March 2003, 25-year-old Josh Ford arrived in Las Vegas from LA to spend time with his family and follow the college basketball event March Madness with his friends.

After a brief conversation with his uncle who told the tech worker about International Game Technology’s (IGT) Megabucks slot machine, he entered the Excalibur Hotel and Casino on the Vegas Strip with just a few hundred dollars in his pocket. Ford had wagered around $100 on the Megabucks machine before ordering a rum and coke and turning his back on the machine only to look back and see the winning symbols all lined up together. At around 1.30pm that afternoon he had won a whopping $39,713,982.25 – setting a record for the largest casino win for Megabucks and slot machines in history.

According to the Las Vegas Review Journal, descriptions of Ford’s reaction ranged from “stoic” to “freaking out right now”. Michael Starr – vice president and general manager of Excalibur – said at the time: “He’s really in shock right now. He called his mother, his grandmother and he is trying to contact his girlfriend. Starr even added that the big winner was not thinking about packing in his job just yet, adding: “He fully intends to go to work on Monday because he has a very big project due on Friday.”

Cynthia Jay-Brennan – $35 million

Third on our list of the most money ever won at a casino is former Vegas cocktail waitress Cynthia Jay-Brennan, who at the age of 37 won a cheque for a staggering $34,959,458 on another Megabucks slot in January 2000. Jay-Brennan was playing on a slot at the Desert Inn for just $3 a spin and is thought to have parted with around $27 when she won the life-changing jackpot.

Described as an “infrequent and careful gambler”, she celebrated by living the high life for a few weeks – marrying her boyfriend and going on honeymoon to Fiji as well as taking care of her family financially. However tragedy struck less than two months later on a family visit to Las Vegas when the car in which Cynthia and her older sister Lela were traveling in was hit by a drunk driver as they stopped at a red light. Her sister passed away at the scene while Cynthia was taken to hospital where she remained unconscious for a number of days.

Upon waking up, medical staff at the hospital told her her fifth lumbar vertebra had shattered, leaving her paralyzed from the waist down. While the offending driver was sentenced to serve a minimum of 28 years in prison, Cynthia was devastated at her disability and the death of her sister but thankful she was at least able to pay off her own medical expenses.

Retired Flight Attendant – $27.5 million

Fourth on our list of the biggest casino wins away from the best online slots is a 67-year-old retired flight attendant, who hit a huge $27.5m jackpot playing slots at the Palace Station Resort in Las Vegas in November 1998. The long-time Vegas resident was a casino regular for 23 years and saw her loyalty rewarded handsomely one Sunday when she was playing on the Megabucks slot machine.

She had initially dedicated to only wager $100 that day but was apparently halfway into her third hundred dollar bill when she hit the jackpot, banking a check of $27,282,539.48 and creating a biggest casino win in history record for the highest Megabucks jackpot win at the time. The woman did not want to be identified – reportedly so she could still visit the supermarket without being bothered – but did plan to share her winnings with her three children and one grandchild.

Michael Masse – spokesperson for IGT who produced the game – said she would be paid $1.1m every year, making that a tidy retirement plan indeed. Amazingly this was not her first big casino win, having landed a $680,000 jackpot in the very same casino just months prior when she had visited with her husband to celebrate his retirement.

Johanna Heundl – $22.6 million

Another retiree who hit it big to make it onto our list of biggest casino wins ever was Johanna Heundl, a former printer from California that celebrated her birthday by banking $22.6m. The 74-year-old was a frequent visitor to Las Vegas and was on her way to breakfast when she called in at Bally’s Las Vegas – now called the Horseshoe Las Vegas – for a spin of the reels.

Heundl was hoping to win one of the smaller $3,000 Megabucks progressive prizes but ended up winning the third-biggest casino payout ever on slots (at the time). She started playing with $100 but when that was used up she put a second $100 bill into the machine and won the jackpot after spending $170. At first she figured she might have won $2m but couldn’t believe her luck when the final amount was actually more than 10 times that figure.

That was the first ever Megabucks jackpot winner for Bally’s Casino, but incredibly the 57th awarded by IGT since they launched the progressive jackpot in 1986. Heundl chose to exercise her option for a lump-sum payment and although she wasn’t sure how she was going to spend the money at the time, she was planning to visit some family in Austria.

Antonio Esfandiari – $18.3 million

Next on our list of the most money ever won at a casino is Antonio Esfandiari, a professional poker player and former magician who landed a mammoth $18.34m for first place at the 2012 World Series of Poker’s charity event dubbed ‘the Big One for One Drop’. The $1m buy-in caused players including Esfandiari to question whether the event would actually take place but eventually 48 players registered in total, a mixture of businessmen and pros.

With a total pot of more than $42m (as well as $5m going to organizer Guy Laliberte’s charity), 39 players lost a million dollars in the course of just one or two days including the likes of Mike Sexton and Richard Yong. The final seven-player table included Esfandiari, a British high roller called Sam Trickett, 1979 world champion Bobby Baldwin, amateur poker enthusiast Laliberte, 12-time winner Phil Hellmuth, hedge fund manager David Einhorn and Brian Rast.

Going into the game’s final table Esfandiari was second in chips with Trickett in the lead, but quickly Baldwin and Rast were bumped off. Laliberte finished in fifth place and was followed by Hellmuth and then Einhorn leaving a head-to-head of Esfandiari and Trickett. Both players were guaranteed to win at least $10m, but the winner would pick up an extra $8m as well as a gold bracelet worth another $5m or so.

Before the tournament Esfandiari – a mercurial character known for performing elaborate chip tricks and playing without wearing shoes – claimed he had a dream where he won the event and that proved to be the case for the Iran-born player. He beat Trickett in heads-up play to win the most expensive tournament in poker to the tune of $18,346,673, with his family and friends hoisting him into the air after the final card was dealt.