Scottish actor Sean Connery (center) as fictional secret agent James Bond sits at a casino card table in a scene from the film 'Dr. No,' directed by Terence Young, 1962. British actress Eunice Gayson sits with her back to the camera in a red, off the shoulder dress. (MGM Studios/Courtesy of Getty Images)
Scottish actor Sean Connery (center) as fictional secret agent James Bond sits at a casino card table in a scene from the film 'Dr. No,' directed by Terence Young, 1962. British actress Eunice Gayson sits with her back to the camera in a red, off the shoulder dress. (MGM Studios/Courtesy of Getty Images)

I leaned against the short stone wall and looked through the palm trees towards the ocean, hoping the deep blue of the Atlantic would help me gather my resolve. Behind me, across an expansive, manicured grass courtyard loomed a black-mirrored fortress with enormous red letters across the front: Casino Estoril.

It was then that the words of James Bond creator Ian Fleming popped into my head. “Do not approach casinos with timidity or reverence,” he once wrote. “They are simply fruit-machines tended by bank clerks and mechanics. Be relaxed and confident… You are one of the few people who take trouble and you are going to win and stop when you have won. You are a person of free will and iron self-discipline who will beat the machine.”

Feeling newly fortified, I turned and faced my foe. I walked purposefully across the lawn to one of the many entrances … where I read the sign that said the casino didn’t open for another three hours. Right. No matter. I decided to go for a coffee and then maybe a walk — a determined walk, mind you — and then press on in three hour’s time.

The reason I was in the sunny, seaside village of Estoril, Portugal in the first place was the same reason Fleming’s words were bouncing around in my brain. The city and the casino are legendary in Bond lore because they’re said to have been what inspired Fleming to dream up the superspy.

Back during the Second World War, Portugal stayed neutral and became something a wartime refuge for everyone from aristocrats on the run from the destruction to diplomats and military officers on both sides on temporary leave. Some of the most wealthy and powerful among them were drawn to idyllic Estoril, just outside Lisbon, and to its then-glamorous casino. Those movers and shakers, in turn, attracted the spies, including Fleming himself.

Fleming, a former British naval intelligence officer, purportedly said he got the idea for the first James Bond novel, Casino Royale, from an experience he had in the Estoril casino in which he played a high-stakes card game across the table from a group of Nazis. John Pearson, author of the biographical The Life of Ian Fleming, writes that this account is quite exaggerated, but that’s beside the point. No Estoril, no Bond, at least as we know him.

So now, more than 70 years later, I followed in Fleming’s footsteps in the service of a little experiment: In the casino that helped create James Bond, I wanted to see if I could use 007’s own gambling systems and strategies to break the bank. If Bond could do it, could I?

Spoiler alert: No. No I could not.

The Many Ways to Play Like Bond

Through the novels and films Bond is shown to be proficient in any number of games of chance, from Baccarat (the game Sean Connery played when the world was introduced to Bond on the silver screen in 1962’s Dr. No, but a game I know very little about) to Texas Hold ‘Em (the game Daniel Craig played in the movie Casino Royale, a game I know well but believe was sacrilege to wedge into Bond’s high-brow universe) to that weird laser-shooting one from Never Say Never Again where Bond and the villain are periodically zapped with powerful electric shocks (I understand most casinos generally don’t spread this game, as electrocuting your customers can be bad for business).

I decided Bond would meet me halfway and together we’d play roulette, the first casino game featured in that first of Bond novels, Casino Royale. (If you’re unfamiliar with roulette, it’s the one with the little white ball that flies around a spinning wheel before eventually falling into a slot with a number from 1 to 36 that rests on either a red or black background — or a 0 with a green background if the gambling gods are angry. The gambler wins if he bet on the correct number, or a set of numbers including the winner or the correct color.)

With roulette in mind, I did a little research and found that at least three different roulette strategies are linked to Bond.* Since I am not financed by Her Majesty’s Secret Service, I played with significantly less money than Bond would ever have dreamed of, but I did my best to test out the three strategies as faithfully as I could.

Here’s what happened:

Progressive Play: Playing a Slow Game Too Quickly

Looking back through Casino Royale, a reader will notice that Bond is described as having won quite a lot of money by playing “a progressive system on red.” Progressive systems generally mean the player changes the value of his or her bets based on the outcome of the most recent spin, but beyond that, the novel doesn’t describe what exactly Bond is doing.

For that, we turn to a seemingly unrelated travelogue called Thrilling Cities written by Fleming a decade after Casino Royale was published. It’s the one where you can find that little pep-talk from the beginning of this story.

In Thrilling Cities, Fleming relates a possibly fictional conversation about roulette he had with a woman in Monte Carlo, coincidentally the setting for Casino Royale, in which the woman asks if James Bond has an “infallible system.”

“Why don’t you let other people in on his secret? Tell me, or I’ll never speak to you again,” she says.

Fleming tells her about a progressive system in which, basically, the gambler bets on red or black (or any other near-50/50 bet) and, if they win, they maintain that bet or something like it. If they lose, they increase the bet based on some quick calculations and forge on, risking more each time they lose. Fleming’s description is very similar to what’s known as the Labouchère system, so if you’d like to learn the details about the betting pattern, check it out here.

I ran into one problem immediately. In Thrilling Cities, Fleming is clearly playing at a casino where the minimum amount he can bet is not very much relative to his bankroll. Casino Estoril is not so kind to a journalist’s wallet and I was forced to put more on the table per bet than I was planning originally.

With the money I had I could attempt the progressive system, but I wouldn’t be able to weather even a short string of bad breaks in a row. It was going to be close.

On the plus side, perhaps the best part about this system is that it requires the you keep track of your betting on a little notepad with a pencil and paper. Along with a suitably half-serious-half-bored expression, this gives the impression to onlookers that you know what you’re doing, when in reality, you’re taking your cues from a fictional secret agent and maybe made-up conversation.

Anyway, for the first spin I placed my bet on red, as Bond had done, and waited while the white ball bounded around the whirling wheel, threatening to make me a richer or poorer man with every bobble. It finally came to rest on 28. Black. Huh. Bad luck right off the start.

Sticking with the system, I increased my bet as instructed and stuck with red. I would not be deterred. And for my fortitude, I was rewarded twice in a row: 32 red and then 18 red. Things were looking up.

But then, a hurricane. 11 black. Increase bet. 10 black. Increase bet. 13 black. Busted.

Fleming had described playing with this system as a long-term endeavor and made a big fuss about ensuring you have a chair at the table to endure the grueling, hours-long process. It was over for me in less than 10 minutes.

The Back-Up: A Bond ‘Favourite’

I didn’t come all this way to gamble for less than 10 minutes, and luckily the progressive system was one of two mentioned in Casino Royale. The second, described as “one of Bond’s favourite [British sic] gambits,” is spelled out clearly in the novel and is more straightforward: The gambler places two bets, each covering a set of 12 numbers, meaning out of a total of 37 numbers, 24 are covered by the bet. The bet stays the same every time.

In this strategy, the gambler is risking twice as much for less of a profit per spin, but in exchange, they should win more often — nearly two-thirds of the time. (It’s “nearly” two-thirds of the time and not exactly two-thirds because the green 0 throws all that very clean math off for everyone.)

Because the minimum bets aren’t any more affordable for the one-third bets, I had the same capital problem as before, in that I would not be able to survive for long if things didn’t go my way. Luckily, this time fate was at least not trying to embarrass me.

Unlike before, I varied the sets of numbers I was betting on from spin to spin, alternating from backing the lowest and middle thirds to the middle and highest thirds — for some reason I felt compelled to keep the middle numbers in the mix most of the time.

Things looked bleak from the start, as somehow I managed to whiff on my two-thirds bet twice in a row. I was immediately in danger of going broke again. But then I went on a streak, hitting eight wins out of the next nine spins.

At this point I was up a modest amount for this phase of the experiment and, if I had listened to Fleming’s pep-talk more closely, I would’ve walked out the door. But I am apparently a person lacking some amount of “free will and iron self-discipline,” so I kept playing.

What followed was a slow, seemingly inevitable downhill slide. For the next eight rolls, I connected on half — remember I was losing twice as much as I was winning — leaving me just a hair down from my original buy-in. I decided to quit while I was behind.

The Dumb One

Alright so this one isn’t strictly a James Bond bet, but for many people Sean Connery is the true Bond and this is his bet. The story goes that in 1964, Connery visited the Casino de la Vallee in Saint-Vincent, Italy and made a simple, long-shot bet: only the number 17.

Betting on a single number, out of 37 possibilities, is what a mathematician might call not-the-best odds. But Connery hit. And then did it again. And again. Single number bets pay out the most, so Connery walked out of the place a fairly rich man.

So I had a go and bet on 17. (I actually splurged a bit and also bet on 22, the number guaranteed to win on the rigged roulette table in Casablanca.)

It won’t be much of a surprise that 17 did not magically hit for me — not the first time or the other three times I tried throughout my time in the casino. No 22 either. Both did occasionally pop up, but never when I had made this particular bet, so that doesn’t count.

Conclusions: When The Money(penny) Runs Out

At the end of the day, I came away a poorer man for attempting to use James Bond’s gambling strategies in Fleming’s casino. What I’ve learned is this: I am not James Bond (or Sean Connery), but more importantly, I don’t live in the James Bond universe.

That’s a universe where Bond has a system that actually beats the house, because it’s also the universe where he can drive a motorcycle off a cliff and skydive into a crashing plane and save it. What do you mean someone actually did that last part? Well, you know what I mean.

So I didn’t throw an obscenely large tip to the valet and hop in my Aston Martin to motor on down the Portuguese coast. Instead, I left the casino and quietly walked down through the courtyard, lit beautifully for the evening, to the beachfront train station. There I waited on the next ride to Lisbon.

And that’s where I decided: I don’t need better gambling strategies, I need better screenwriters.

*There is a fourth system bouncing around gambling websites that is literally called the James Bond Strategy, which involves covering more than two-thirds of the table and the number 0 with three bets of varying value. But for the life of me, I could not figure out where — in what book or film — the strategy came from. If you know, please let me know. Since I couldn’t confirm it’s connection to Bond, and more importantly since it required a lot of capital per bet and I was already running low on funds, I forewent this particular play.

Lee Ferran is an Emmy Award-winning investigative journalist and the founder of Code and Dagger, a foreign affairs and national security news website.