Biggest Gambling Wins With the Martingale

Bag of Money With Casino Chip and Roulette Wheel Background

The Martingale is the most-famous betting system of all time. It calls on you to double your wagers following every loss.

The Martingale is both simple and effective, but it’s also extremely risky. This strategy creates the potential for losing all your money more so than with any other betting system.

Nevertheless, some gamblers still use this system while chasing riches. Certain players, including the ones covered below, have made millions using the Martingale.

Charles Wells

Who Is Charles Wells?

Charles Wells is one of the most-famous gamblers of all time. Interestingly enough, though, he wasn’t a gambler by trade.

Wells was an nineteenth century conman who tricked people into investing in his fake inventions. The key word is fake, because he never intended to create any of the products he proposed.

Drawing of Gambler Charles Well

The Brit’s best skill was convincing investors to give him money—not inventing things. He even managed to trick people into giving him a collective £4,000 for a musical jump rope.

Wells never had any intention of using the £4,000 (approx. £130,000 today) to work the fabled jump rope. Instead, he used the money to go on a gambling excursion in Monte Carlo.

How Did Wells Get Rich Through the Martingale?

Wells began playing roulette when he arrived in Monte Carlo. He started experiencing success almost immediately.

The conman suddenly looked like a professional gambler as the chips mounted in front of him. He managed to break the bank over a dozen times during the trip.

Breaking the bank refers to winning every chip at a table and, subsequently, shutting it down.

Wells walked away from his first trip with over 1 million francs (approx. £4 million, or $5.2 million).

He returned to Britain for a short while only to decide that he wanted another go at Monte Carlo. Wells once again experienced incredible success and won even more francs.

Upon returning to England this time, Wells had suddenly become a nationwide celebrity. Many people wanted to know the reason behind his success.

The conman lied his way through interviews by saying that he devised a secret strategy. The spoiler is that he was merely using the Martingale.

Wells made the fateful mistake of taking a third trip to Monte Carlo. Beforehand, he decided to defraud more people and purchase a yacht with his earnings.

Karma would catch up to Wells as he lost all his money to the casino. He returned to Britain and was immediately arrested for fraud. His final years were spent rotting in prison without a pound/franc to his name.

David Choe

Who Is David Choe?

David Choe is an American artist who has painted famous murals and designed album cover art for Linkin Park, Jay-Z, and more. His painting of Barack Obama is featured in the White House.

Despite his talent, one of Choe’s most-memorable works has nothing to do with his skill. Instead, he did a mural for Facebook’s office that ended up netting him $200 million.

Choe thought that Facebook would never succeed in the long run. Nevertheless, he liked Mark Zuckerberg and the other FB figureheads.

So, he painted them a mural in exchange for Facebook stock. His shares ended up being worth $200 million when the company’s IPO launched.

How Did Choe Win with the Martingale?

With a famous art career and numerous Facebook shares, Choe obviously didn’t need gambling to get rich. Nevertheless, he found success on the casino floor too.

Casino blackjack became his game of choice. Choe employed the Martingale and set a stop-win limit for each session.

A stop-win limit refers to when a gambler quits playing after meeting a desired win target. Choe even brought a friend along to make sure that he quit sessions after reaching his goal.

In an interview with Howard Stern, the artist spoke of how he started gambling with just $500. He ran this total up to $1 million strictly through the Martingale and stop-win limits.

This gambling story is impressive enough. However, some of the side stories that Choe told on Stern and the Joe Rogan Experience podcast are even more interesting.

The Las Vegas Review-Journal chronicled some of his Las Vegas adventures in 2014. They recounted how Vegas rolled out the red carpet to keep Choe gambling.

“The height of my Vegas experience was staying at the penthouse in every single casino — like all the high-roller casinos — a harem of whores in each one,” he told LVRJ.

“I would be going to Vegas all the time with 100 grand. A million dollars in, like, a pillowcase in my backpack.”

One casino even sent a private jet to Choe’s Burbank, CA home. He and a friend rode on the “giant, empty plane” to Las Vegas.

Other gambling establishments let him ride in “secret elevators,” offered him illegal drugs, and threw more women at him. He didn’t want the drugs, but he definitely appreciated the women.

Choe’s lavish lifestyle and Martingale winnings came to a halt when he suffered an angina attack (form of heart disease) at age 35.

He hadn’t slept for five days and began losing his sense of balance. Finally, Choe collapsed on his penthouse floor with $20,000 chips spilling out of his pockets.

After waking up from the angina attack 36 hours later, he wanted to start playing blackjack again. However, his friends talked him into returning home to Burbank and leaving the wild Vegas lifestyle behind.

John Henry Martindale

Who Is J.H. Martindale?

If you think that the name John Henry Martindale sounds familiar, you’re right. He invented the Martingale system, or at least holds credit for the idea.

J.H. Martindale was a casino owner in London during the eighteenth century. He was a hands-on owner who frequently mingled with his customers.

During these conversations, he’d give advice to gamblers. One of his biggest pieces of advice was to double bets following losses.

How Did Martindale Win Through the Martingale?

J.H. Martindale didn’t win by gambling with the Martingale. Instead, he made money for his casino by talking players into doubling wagers after losing.

This is a risky betting strategy compared to others when considering that many players book small, consistent wins with this system. In the end, though, Martindale felt that the house would always come out on top.

He was right in most respects. The Martingale can reap plenty of small winning sessions. However, a gambler’s luck will eventually run out if they keep employing this strategy.

Should You Use the Martingale to Win Big Too?

The Martingale has remained popular for almost two centuries. The main reason why is because it works…at least in theory.

Here’s an example to show the power of the Martingale:

  • You bet $10 and lose (bankroll at -10).
  • You bet $20 and lose (bankroll at -30).
  • You bet $40 and lose (bankroll at -70).
  • You bet $80 and lose (bankroll at -150).
  • You bet $160 and lose (bankroll at -310).
  • You bet $320 and win (bankroll at +10).

You’ve lost five bets in a row in this example. But despite winning just one out of six wagers, you’ve managed to book a $10 profit.

The Martingale is seemingly a foolproof system. It could work under the perfect conditions. The problem, though, is that such conditions don’t exist.

Monte Carlo Casino

First off, you’d need to find a casino without table limits. Otherwise, you’ll eventually reach the table limit during a losing streak and not be able to double your wagers any longer.

Secondly, you’d need an infinite bankroll to ensure that you never risk losing all of your money. Maybe Jeff Bezos can pull this off, but not you.

Of course, the odds of you going on an insane losing streak are low. The longer you play, though, the more likely you are to run into such a horrific occurrence.

If this happens, then you have no recourse since your bankroll will be gone. Long story short, use the Martingale at your own risk.


Most gamblers don’t use the Martingale (at least consistently) due to the reasons outlined above. But you can see from the stories of Wells and Choe that it’s possible to win big with this strategy.

Each player earned seven figures using the Martingale. Wells actually pulled this feat off twice during trips to Monte Carlo.

However, you should temper your expectations with this system. The Martingale can deliver frequent winning sessions, but it also takes a while to build your winnings. The story of Choe playing for a year before hitting $1 million illustrates this idea.