We all hope to hit it big at the casino. For most of us, winning a few thousand dollars would be the dream come true. Then there are those who lived the dream writ large. They won millions instead of thousands, and the payoffs were life changing. Making these victories even more special, they got snagged in single sessions, not over the course of multiple nights spent grinding it out.

What does it take to rack up a jaw-dropping win? Sometimes, you need strategy and a knowledge of the game you’re playing. Always, there looms the unpredictable luck factor, which invariably plays a key role in massive payoffs at the tables. And finally, since one never knows when luck will strike, there is something to be said for putting up the money and being game to go for it.

Here are some of our favorite big winners, people we salute for their abilities to keep wagering and to not quit until they got to where they wanted to end up. 

Media Baron & Casino Crusher

Kerry Packer holds the crown for being one of the biggest and most prolific gamblers in the world. The Australian billionaire’s  winningest night of all? A 1997 run he had at the MGM Grand in Las Vegas. He is said to have played blackjack for $200,000 per hand, covering six spots at a time. So, each of the dealer’s hands had $1.2 million on the table with Packer giving himself six opportunities to win or lose.

During this infamous streak, he clearly won more than he lost. In fact, the wins are so large that it is unclear exactly how much he ultimately took down. While it’s reported to be as much as $40 million, a pal who was there has claimed that the total is closer to $26 million. Whatever the case, the sum was jaw dropping. And not just for him. When all was said and done, Packer reportedly tipped the MGM crew $1 million. Clearly, it was a good night for everyone – except for the holders of purse strings at MGM Grand.

It’s Never Too Late to Score Millions

While it’s easy to believe that gambling is best enjoyed by young people, Johanna Heundl is an exception to that rule. 

She proved her mettle in 2002 while celebrating her 74th birthday in Las Vegas. Like almost everyone visitor to Sin City, she figured that she would take lady luck for a spin.

Heundl did it via a progressive slot machine at Bally’s, laying out $100 to try winning the $3,000 progressive. But that didn’t work out. Her money got drained. Rather than quitting and heading off for eggs or pancakes or whatever, Heundl ponied up another 100 bucks. 

Things were not looking good on the rebuy until, some $70 in, she hit a jackpot that far exceeded $3,000. Heundl was thrilled with what she believed to be a $2 million payday. When staff strolled by, though, she found out that she was wrong.

In fact, her payout was $22.6 million. Clearly, it was the greatest birthday present imaginable and nobody complained about her being late for breakfast.

Slot jackpot

Squeezing Tropicana

The professional gambler Don Johnson has won tons of money and reaped loads of comps from casinos around the world. But his most stunning win has got to be the one that he engineered at the Tropicana in Atlantic City. 

As with Packer, Johnson excelled at blackjack. He found his edge by demanding advantageous rules: a hand-shuffled six deck game, re-splitting Aces, dealer stands on soft 17 and a 20 percent discount on losses. 

All of that, combined with incredible luck – as Johnson has acknowledged to me – allowed the blackjack whiz to fleece the Tropicana out of nearly $6 million over the course of an on-fire 12-hour-long session in 2010.

For obvious reasons, Johnson was unenthusiastic about the world getting wind of his massive takedown. But that became impossible after bosses at the casino made public that its poor financial showing for a particular quarter was due to the win of a player named Don Johnson.

The revelation gave Johnson notoriety in the gambling world, but it also led to casino managers handling him with care and, eventually, not providing him with the rules he needed to keep winning. But Johnson doesn’t mind all that much. Blackjack was just a side hustle for him. He makes his real money handicapping horse racing, and that continues to go strong.

Clocking the Wheel

In his book “Gambler: Secrets from a Life at Risk,” the world-class sports bettor Billy Walters writes about clocking roulette wheels

He put together a team of people who traveled to casinos around the United States and found biases on the wheels. After all, they are mechanical devices and prone to mechanical glitches. Recognizing the wheels with specific biases that resulted in certain numbers hitting more often than they would if the game was completely randomize, he set out to win millions of dollars.

Among his biggest scores: nearly $4 million, aced during a 38-hour session at the Golden Nugget in Atlantic City, which was then owned by Steve Wynn. Walters bet $2,000 per spin on the same five numbers: 7, 10, 20, 27 and 36. He managed a magnificent profit at a game that statistically comes out on top against gamblers. Of course, though, with his hard-earned knowledge, Walters was not exactly gambling.

Putin’s Prize

This, strictly speaking, is not a gambling win, but it did come down in a Vegas casino, it did happen in a single session and it is too juicy to not include among our favorites. 

In 2018, the Russian UFC star Khabib Nurmagomedov successfully defended his lightweight title in a match against Conor McGregor. According to UFC President Dana White, Nurmagomedov was on his way to the dressing room when he received a call from Vladimir Putin. The Russian strong man, according to White, “gave him and his father like $20 million worth of property in Russia.” As far as we’re concerned, that’s a heck of a Vegas win.

Maybe Putin was impressed by Nurmagomedov post-victory tactics: He jumped into the crowd and mixed it up with a teammate of McGregor. 

And while the real estate windfall is nice, it’s hard to keep from wondering what Putin might have done if Nurmagomedov had lost the match.

Michael Kaplan is a journalist based in New York City. He has written extensively on gambling for publications such as Wired, Playboy, Cigar Aficionado, New York Post and New York Times. He is the author of four books including Aces and Kings: Inside Stories and Million-Dollar Strategies from Poker’s Greatest Players.

He’s been known to do a bit of gambling when the timing seems right.