The Martingale Roulette Strategy: Does It Work?

THE Martingale Strategy (not to be confused with my Espresso Martini strategy in the North End) is one of the most well-known and widely used roulette strategies.

In essence, The Martingale Strategy involves doubling down on your wagers, similar to how I double down on bottles at the club when fine looking ladies approach my table.  

Both are risky strategies and can cause you to lose a lot of money in the long run. If you find yourself chasing losses (can be applied to both gambling and women) because you have gambled and lost more than you should have, make sure you speak to somebody before employing such a risky strategy again in the future.

Maybe, you have implemented this strategy while visiting a casino, like Encore here in Boston, and you may have used it when you have gambled online during the day while waiting for the clubs to open. Either way, here is “The Pit Boss” review of The Martingale Strategy and whether or not it can help you recover from losing streaks.


AS I discussed in the opening section, The Martingale Strategy involves consistently doubling your bet if you are losing. The theory is that you will eventually win one and recoup your initial loss.

My buddy Mahduil does this with women. He hits on every single piece of tail that comes into a bar, lounge, club, cafe, library, gym, event, restaurant, gas station, bus stop.. you name it. He even tells women he’s a professional photographer in hopes that they will cozy up to him and let him take their pictures. The day they taught “boundaries” in elementary school, he was clearly absent for the lesson.

This guy is more aggressive than the Barbary Lion attacking a herd of sheep at dinner time up in the Atlas Mountains of my native Morocco. Recently though he found a lady willing to give in (give up?) and give him a little action, hence making The Martingale Strategy ultimately to work in his favor.

However, in theory, you could follow this strategy to the bottom of the barrel and not win any money -or women. This is because roulette is a game of luck, and no proven strategy will help you win. I’m not in the business of selling you false information, and you must be aware of the risk.

You can use maths and probability to bet on the more likely outcomes you face on both the roulette table and the VIP table at the club. However, this doesn’t mean a win will materialize for you during either game. Always remember this when trying to pinpoint a strategy you want to use in your personal game.

Artax and Arteyu in The Swamp of Sadness, The Neverending Story

Chasing the excitement of pulling yourself completely out of the mud is clearly one of the big draws of gambling. Until his recent score, Mahdiul was deeper in mud with women than Artax was traveling through the Swamp of Sadness with Arteyu in The Neverending Story. This is -at least partially- what makes that taste of victory so sweet though.

In fact, one of the main buzzes of entertaining roulette games is the pleasure of trying to secure a get-out-of-jail spin, which puts your fund back to normal. This isn’t the only way to have fun in a casino, but for those looking for an adrenaline rush, it is one of the most exciting.

The theory is fairly obvious, but I will explain it to you in my Lil Boss terms for clarity.

Let’s say you bet $5 and lose it. Under The Martingale Strategy, your next bet should be $10. If you lose the $10, you double down again, betting $20 and winning the return is $40. This sets you back onto an even keel and will allow you to continue into the next game.

Mahdiul using The Martingale Strategy at a lounge.


AS I have covered in this piece, it is probably glaringly obvious what this strategy’s positives and negatives are. The most concerning negative is that, in theory, you could ride this strategy down the hole and end up with no money -or women.

While one of these hands could get you out of a sticky situation, The Martingale Strategy does not guarantee that it will deliver results. This scenario isn’t specific to The Martingale Strategy either, as no roulette strategy will result in a guaranteed win.

When A-listers like my good friends -Boston’s own- Matt Damon and Ben Affleck (look for me making a Lil Boss cameo in their next movie) take to the roulette table, they won’t sit at a table and aim to make money or place huge wagers, despite their wealth. It is an added bonus if you end up in profit after a session on the roulette table. However, you must never see a game of chance like roulette as a ticket to financial freedom or any sort of regular income.

For the sake of balance, a huge positive of The Martingale Strategy is that it can get you out of a tricky situation and deliver multiple opportunities to do so. Granted, you need to ensure you have a sizable amount of money. Maybe not the same levels Ben Affleck and Matt Damon have, but enough to have some leeway to swim out of the deep waters.

You have probably heard of the old investment saying, “it takes money to make money” – now, whilst we are by no means suggesting that roulette should be seen as an investment, that same rule applies to your starting fund.

If you can start with a decent bit of money, your chances of implementing this strategy will increase slightly.


IF you are a regular roulette player, you have likely come across dozens of Moroccans, Italians, Chinese, and people from all ethnic backgrounds claiming to have a secret strategy handed down over the years “their people use.” They say this is “guaranteed to see you leaving the roulette table” with more la grana than you started with. Although promising people an ironclad way of winning a game of roulette will bring people to your VIP table at the nightclub, this is not good practice to routinely implement.

It isn’t fair to suggest that you can shorten the odds in your favor, even though as the Lil Boss I probably can do that for you.

Due to the mathematical odds of roulette, you must remember that there’s no way you can spin them positively in your favor. Just remember that the most important thing is to have fun. 

If you find yourself in a position where you no longer enjoy the game and lose more money than you can afford, you must stop and speak to an organization that can help you. Or just join Mahdiul for a night out chasing tail. There are, after all, multiple ways to apply The Martingale Strategy. 

That’s all for now. It’s time for me to “get the f*%k outta here!” See you at the tables!


Soufiane Boutirg, aka “Lil Boss” or “Pit Boss” loves the casino life and everything that comes with it. His favorite casinos are Encore in Boston and Borgata in Atlantic City.

You can also join “Pit Boss” anytime in playing roulette on-line at Cafe Casino. You can find Lil Boss at Lucca on Tuesday, Empire on Wednesday, The Grand on Thursday, Caveau/Mariel Underground on Friday, Big Night Live on Saturday and Memoire on Sunday. On Monday he sleeps.