Gambling Gabriel: Confessions of a Mafia Boss

Do you like gangster movies? Read the story of a gambling Mafia member.

Italy has long been associated with the Mafia and illegal activity. While today this is considered to be mostly a stereotype – one that’s quite annoying – it would be hard to deny the existence of such criminal organizations. People on the inside are claiming the illegal market is larger than anyone can imagine.

Take Gabriele, for instance, or “Gambling Gabriel”, as his friends call him. He’s been in the illegal casino business since he was a teenager. “Back then, we were taking advantage of the poor suckers who were addicted to Blackjack and Roulette. We were cheating them out of their money. Today, it’s all about money laundering,” he says.

His real life has little resemblance to what we’re used to seeing in the movies, but it is still a pretty incredible story worth hearing.

Playing with daddy’s chips

Like most people who end up joining the Mafia, Gabriele grew up in a poor neighborhood. “I’m not going to talk about how my old man was addicted to gambling and kept losing all of our food money or about how my mum developed a drinking habit,” he begins his story.

“Anyway, obviously I didn’t really have any toys and I was playing with whatever I could find around the house. So one day I found these chips in my dad’s room and took them. He found me playing with them and beat me senseless. I didn’t get why he did that. For me, they were nothing but colorful coins.”

Gabriele says he used to roam the streets a lot when he was a kid. Being at home wasn’t a lot of fun for him or his brothers. This is the part that actually happened like in the movies, when he a mysterious man, with the attitude of a wise-guy, grabbed him by the shoulder and asked him: “Hey kid! Would you like to earn some easy money?”

He looks down to the ground and you can see on his face that his mind has drifted off. “This must have been like… what? Forty years ago, maybe?”

How it began

One small job led to another and soon enough he was introduced to nearly everybody as “a friend of ours”. “I wasn’t a stupid kid, but I wasn’t too bright either. I would have liked to go to school and get a fancy PhD or something, but that’s just not how life worked out, you know?”

Back then, the crowd Gabriele joined was running illegal gambling dens, so he started working as a croupier. “There were no machine guns or anything like that, like you see in the movies. We didn’t blow anyone’s brains out, but I did see a few guys get beat up real bad for not being able to pay up.”

Gabriele says he sometimes felt sorry for his “victims”. They were mostly gambling addicts, blowing all of their money on one game. “I guess they reminded me of my dad. But in the end, they were doing it to themselves. Sure, we had ways of cheating and making sure they lost. That was our thing. Most of the time we didn’t have to make much of an effort; these guys wouldn’t stop until they were broke.”

There was a lot of money to be made in the illegal casino business and Gabriele saw it as a way to provide for his family. “I never ate alone. I always helped whoever needed it. I tried to take care of my. It’s funny how they never seemed to care where the money came from. I guess they suspected it was better if they didn’t know.”

Running the business

A few years later, Gabriele was running his own casino. An illegal one, of course. “I loved it. I loved coming in to work, taking care of everything, making sure things are under control,” he says.

At this point, the business wasn’t really about cheating people out of their earnings anymore. It was more about money-laundering. “We were running a lot of illegal businesses: prostitution, drug dealing… you name it. How were we going to explain where all the cash came from? We needed a money laundering operation that we could trust and the gambling business was perfect for this.”

As head of the illegal casino, his main task was to avoid trouble and this meant making sure that customers kept quiet. Some needed to be intimidated and he had just the right people to take care of this. Others were worth keeping close, as friends. “I knew every cop on the block. I knew what they liked, what their wives liked and exactly how much I needed to stuff in their pockets.”

The winning strategy

All in all, business was good. “I ran one of the best Italian poker rooms!” he says proudly. Gabriele ran the place for several years, but eventually moved on to something new. He claims he is still “in the industry” today, but he’s reluctant to revealing any details, for the obvious reasons.

“Nowadays, the Internet is everything. Personally, I don’t get it. If you ask me, it’s just stupid. But hey, people like to gamble and they’re lazy, so they need online and mobile casinos.”

Gabriel has seen a lot of things and he certainly has enough stories to write an entire book. And while he could probably tell you everything about Poker, Blackjack, Roulette, Baccarat and how to win at these games, he claims he never placed a wager in his life.

“Since that day when my dad gave me that beating, I have never touched another chip in my life. I don’t think gambling is necessarily bad. I just avoid it. It’s important to know all the rules to all the games, but I prefer to watch from the side. This way, I never lose.”