What an Old Gangster Taught Me


Yes, he was a real Chicago gangster. Old style. Black coat, white shoes, black hat…a real time bomb! A man who knows why backward rear passenger doors are called “suicide doors” and why the Mob might favor that style of sedan. (hint: it is not this lame explanation about perceived safety)A man who perhaps dated Sam Giancana's daughter. Sure maybe not a lieutenant, but a “special” individual in the organization. And boy he was “special”, but I say too much already.

It is a shame that his TRUE story can never be told. He was a very smart man, maybe the smartest I have ever known. Certainly, he was someone who taught me how intellect could be useful in the practical world. He taught me that brains were useful not just in esoteric and arcane academic fields like mathematics, astrophysics or computer science, but were invaluable in real life.

He taught me so much that putting it all down here is not possible, but I can at least pass on some of his pearls of wisdom. I can at least tell a little bit about his world view if I cannot tell too much directly about him. I think the “civilian” world can gain some insights by considering these bits of wisdom I gleaned from an old gangster.

“Money is a thing. You can’t eat it or sleep with it.” Money is tool. This is an especially hard one to embrace, so I have put it first. America is so much about chasing the almighty dollar. Plus you are taught to think crime is all about greed, but maybe that isn’t true. Money is a tool, not an end goal. As a tool, you use money to fix something or build something. Money is a thing. It is not alive. Living things matter more than money. Love matters more than money.

Don’t make other people’s mistakes. You will make plenty of your own, but you can live with them when they are your OWN mistakes.” Always consider things on your own personal and moral scale, never use other people’s yardsticks. The latter can lead to great regrets. The fact is that if the rules don’t apply, then maybe the rules need to be bent. Take your own counsel, ALWAYS, because someday it may be the only counsel you have. Reality is truly a life or death battle, so you need to be able to make your own decisions about who might need to be killed or spared or protected.

“The good guy/bad guy stuff is fantasy.” Criminal behavior is often driven by circumstances. It is not ALWAYS, but often. This means a person’s true nature cannot be extrapolated from the hat they wear at the moment. Not to mention, the good guys called police are not always your friend no matter what hat you might be wearing. They are just another gang, the blue gang, and you should steer clear.

Those funky Libertarian conspiracy theories about the mob’s involvement in the Kennedy assassination are not crazy. However, if they are not wrong, then what are YOU going to do about it? What does it REALLY mean?” This is just further proof this narrative about the “good guys” and the “bad guys” is largely fabricated. The reins of power are held by many corrupt individuals. War is a racket. The government is in bed with the mob. The “powers that be” are the most feckless amoral jack asses you can imagine and there are no real differences here. The nihilism, especially in politics, of my old gangster advisor, cannot be denied. Yet he loved life and held his family close. If you know the game is rigged, you just aren’t going to believe in the mainstream narratives.

Here is one directly related to intellect,” They will always hate you because you are smart.” What he meant by that was that brains are a serious advantage, if they are properly applied. Everyone who is not blessed with brains will be very jealous. It is not something that you necessarily need to hide, but you should not throw it in people’s faces either. It is better to just let your braininess organically leak out in your personal interactions. You won’t be able to hide it, but let people figure it out. Definitely, don’t tell people you are smart or correct people’s grammar. Brains could actually be perceived as a threat, so be modest. You do have an advantage after all.

Here is another one that is especially useful to someone like me on the autism spectrum. Most likely I am a classic case of Asperger’s Syndrome. In any case, this next one is very important for me to keep in the forefront of my mind given my poor abilities at reading people’s emotions and intentions. “Do not ascribe bad intentions to people’s actions, when ignorance suffices as a likely motivation.” Basically, people do what they are going to do mostly for their own reasons. They are not “thinking all the time”, but rather they are just “reacting” to life. Most people are so caught up in their own lives and their own emotions that they are barely paying attention to you and how you feel. They are certainly not considering how this or that might make YOU feel. If they hurt your feelings or piss you off, it is most likely they are completely ignorant as to how their actions make you feel. They barely know why they are doing anything in their lives.

Finally, here is a very important idea that has served me well. It has been proven true over and over again. Throughout your life, you will be seeking to accomplish this or that thing, but if everyone could do this or that thing, EVERYONE would do it. If wishes were horses, then beggars would ride! This basic idea that he presents applies more than ever in a society that has abandoned meritocracy for corruption. There is a reason why not everyone is successful and here is why. You have to think out of the box and you have to have facts. Information is KING!

There is how YOU THINK it is. There is now THEY tell you it is AND there is how it REALLY is.” What this means, in a nutshell, is that book learning is not enough to succeed. You can read about it or watch YouTube videos about something to try to figure out how you think things work. There is how the “authorities” or the “experts” tell you IT IS, but there are real-world rules at play all the time. The trick to success is finding that person that knows how it REALLY IS. The real world “lay of the land” is invaluable at succeeding in life.

I feel I should pass on some piece of real-world knowledge that I did not exactly learn from my old gangster friend, but he certainly “hinted” at it. He often said, “Everything is negotiable EXCEPT virginity.” That piece of knowledge that you need to know how it REALLY IS sometimes requires negotiations. Sometimes it means putting out some cash. It is amazing what the financial motivation of a “double sawbuck” or a “C” note can bring. How does one pull that off?

Well, determine how much the piece of knowledge is worth to you and how much cash you actually have, then collect up that amount of cash. In cash, real cash bills in hand. Hypothetically, let us say that you have determined that you have a $100.00 to spend to get this piece of real-world knowledge. First get the $100.00 in pieces, like five twenties. How do you “signal” the other person that there might be some extra cash in it for them? Well, you might ask a question and get the “establishment” answer that they are “supposed” to give.

Maybe the answer is “You have to have a work order for me to do that.”

That is when you reach in an pull out one or two of those double sawbucks and say, “What if I have a work order like this one?” You proceed to show them the money. If they are still unmotivated, then show them the rest of the money, in portions. That is the reason to not just start out with a ‘C’ note.

The hundred is all you have, so you cannot escalate, the way you can if you have broken it up into pieces. Maybe a couple of twenties is not motivating, but four twenties are sufficient and you saved twenty for yourself. As life goes on, you will likely be dealing with a lot of ‘C’ notes given inflation and all.

Don’t use the term, “bribe”. Its is not a bribe. It is a transaction. You need to know how it REALLY IS and sometimes that is a hard-won piece of knowledge that someone will not part with without sufficient motivation. There are no real rules in life and often it is unfair. It is up to you to navigate the obstacles that will surely appear along your path. Charm people with friendliness, use your brains to evaluate where you want to go in life and then find out how it REALLY IS, so you can get there.

The above wisdom needs to be taken with a grain of salt. My old gangster friend was a hella big liar. I used to tell him, “ You lie like a rug!”

He would laugh. I think sometimes he was or sometimes he was just doing a little exaggerating. Other times a shadow would cross his face and his pupils would darken as he showed me a bullet wound or would tell me a story so stark and real that the hair would stand up on the back of my neck. If I watch the movie Casino, I get that same chill on the back of my neck. I recall how he thought I might cross him on some matter. A matter that I was perfectly earnest in so I stood tall and spoke bravely about “…how fear is not going to motivate my actions.”

But it was ALL bravado, because when he calmly said, “If you cross me, I will stuff you in a trunk, Tony.” I KNEW he was not lying!

R.I.P. my old gangster friend, yes I feared you, but I loved you too! Because well, “Nothing is more important than family.” Perhaps the most valuable lesson of all that one. I miss your practical real-world advice and your love every day.

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