top of page

Is Jay Gatsby A Gangster? – Op-Ed Piece


Table Of Contents



Hey readers,

We got two birthdays today, a great coffee place for you to check out, a poem by Langston Hughes and a crazy theory about Jay Gatsby.

Follow us on Facebook, Twitter, or Instagram.

Subscribe to our blog if you want to receive the weekly newsletter.

Thanks. Enjoy reading.


Writer's Birthday

We got two birthdays today.

Kenneth Grahame was born on July 20, 1859. He wrote The Wind In The Wallows, a classic in children's literature. Learn more about him here

Martin Provensen was born on July 20, 1916. He worked with his wife Alice Rose Provensen to illustrate 40 children's books. Learn more about him here.


Writer's Favorite Drink

Here is a coffee place you may like.

Address - 51 Astor Place, between E 8th and E 9th St

This Australian coffee shop sees a lot of foot traffic throughout the day, but still has seating for those who want to sit and stay awhile. I don't know about you but I take my time when I eat. These words don't write themselves, and more importantly, that salmon toast doesn't eat itself. Huge windows brighten the space and offer views of the bustling city outside for writers seeking inspiration. So if you want to make wiseass remarks about all the people walking so fast yet going nowhere, or writing that blog post you are supposed to finish by the end of the night. (You should probably do the latter) A full lunch/brunch menu will keep you fueled for an afternoon of creating. Between the salmon toast and my sarcastic mind, I am not getting much done when going here, and yeah, yeah, I know that some of you would say there is no difference, between me working and not working, but are you really about to argue with me about a place that sells salmon toast?


Short Poem

“So Tired Blues” by Langston Hughes

With the sun in my hand

Gonna throw the sun

Way across the land-

Cause I’m tired,

Tired as I can be


Is Jay Gatsby A Gangster? – Op-Ed Piece

The character Jay Gatsby is one of literature’s most enduring and fascinating characters. His fall is one of the reasons that many consider the book to be the epitome of a modern novel. The Fitzgerald book is all a novel should and try to be, with its elegant verse and nicely paced plot. This timeless classic has even come to define the American Dream and presents questions as to what that idea even means. Does the American Dream exist? Is it attainable? Or is it a lie that we are all aiming for? Like many great books, there is more to the surface which is why so many of us love it after all these years. I, for one, have written about Fitzgerald already, and I plan on writing about the guy many more times here. He was a genius, in my opinion, and possibly the best writer of all time. Yes, I mean better than even Shakespeare. All I am saying is that if he and Shakespeare were both given a week to write a story, I think that Fitzgerald’s story could compete with The Bard’s. If Fitzgerald was alive today, he would be the best writer alive, without a doubt. No one would come close to him. That is how brilliant I think he was.

Jay Gatsby is a perfect dichotomic character, showing the flaws in his goodness, and the strengths within his corruption. He is not perfect, and he is not meant to be, and that is why so many love him.

He has everything. He has a big ass house that many would love to live in. He hosts extravagant parties that many would like to attend and drink and enjoy themselves. He has an enormous wealth where such parties don’t affect his living. The guy has it pretty good. Most would sign up for that. I know I would.

“Hey Greg, do you want to have a big house, host the best parties, and be really rich?” I mean, yeah. Why wouldn’t I want that again? As compared to not having a big house, never hosting parties, and not being rich?

There is something else to Gatsby, though. Small print that no one ever reads about the character. He is not happy. He is alone and, most importantly, not in love. He has the love of his life, Daisy. Some may say that he has these parties to forget about her or to even impress her. But they are not meant to be. Daisy has moved on with her life and is with another man. She doesn’t love Gatsby anymore. As B.B. King said, the thrill is gone for the two. They are no longer the young in-love couple that they once were. Daisy accepted that. Gatsby has not.

Jay Gatsby – the man who has everything but yet has nothing.

In modern times, you could probably compare him to one of those billionaire entrepreneurs that have a 45-million-dollar house with seven bedrooms and 12 baths and that are planning on going to Mars in the future. These people are too rich; if that is such a thing. They have so much money that they quite literally don’t know what to do with it. I know, while you and I are putting together some money for our next pizza pie and complaining that the price for retail items keeps going up, these people are drowning in money. That is Jay Gatsby, for you. Richer than any man deserves to be.

Let’s get back to Gatsby’s happiness (or lack thereof). What are you if you aren’t happy? If you can’t enjoy your time while on this Earth? Does the material world mean anything if you are empty on the inside? No, it doesn’t. So when I say that I want to have all that Gatsby has, as I am sure many of you would answer with a similar provocation, I assume that my mindset is inheriting the items he has obtained with his wealth. I am getting a house and parties and money while still being me. I am only getting an upgrade to my life, not changing myself. (This begs to question if the poor you that can’t afford anything is the same as the rich you that has too many cars, but that is for another day) Despite some of the upheavals and many failures that have come my way, I am happy. I like myself and the man that I am. Sure, I am not perfect, big surprise there, someone call M. Night Shyamalan, but I am okay with that. I wrote about this before during the pandemic. All and all, I like me. Jay Gatsby doesn’t like his life. He is not happy. There is no size mansion full of sculptures and paintings, or a large party with rare wines and fancy outfits, or an expensive check with enough to get you anything that can make you happy. At the end of the day, if you don’t find happiness, everything else is mute.

You can’t buy happiness or, as the Beatles said, love. And that is true. The sadness that Gatsby feels because of his lost love with Daisy has to end, and it doesn’t, and that is pretty sad for him. He can’t move on. You can easily view it as pathetic. Like someone should shake him and say, “Get it together, Jay! Move on already!” And what happens when he does that? He finds himself as the man that he truly is, one that no one mourns at his funeral, which has to be the saddest thing anyone can have to happen to them.

The question of inheritance is viewed differently when you learn that your own happiness is not built on it.

  • Small house with only two rooms, or a large mansion with four guest rooms.

  • Small parties with only a few friends or enormous parties with everyone in town.

  • No money in your wallet or a wallet of Franklins.

Those don’t affect that part of you that is not controlled by money. And yes, there is such a part. Despite our society’s obsession and need for financial security, there is nothing secure about money for one’s own life to be fulfilled.

Now during these late-night episodes of strangers all over enjoying his alcohol and booze, Gatsby’s professional career is never put into question. Nothing of his job is explored. We are told of his parties, and that is that. Remember that the story is told by a new friend of Gatsby, Nick Carraway, not someone that he has known for a long time. The narrator only knows so much of the guy.

Now, we all know that Gatsby is loaded with so much cash that literary memes can’t help but be filled with them But let’s look at the story from a historical perspective.

How rich was Jay Gatsby?

The book never gives a number, but we can assume he was one of the richest men of his day. So rich that others who were rich would be impressed by his wealth. Think of a person who has parties every weekend at their luxurious mansion for anyone to attend, and then how rich that person is; that is where Jay Gatsby’s money falls into play. I bet he would have multiple driveways that have different exits. Let me tell you, I had gone to those places when I was a delivery boy, and that is a different world. They had a house for their maids. I left, in my humble Saturn, a different way from where I entered. Normally I pull in and out of the same driveway. Gatsby wasn’t rich. He has, as I like to call it, property money; he was so rich he owned shit that we regular people could not even dream of owning.

Who was the richest person in Gatsby’s time?

Gatsby is living in the 1920s, so we have to ask ourselves. Who were the rich people back then? What fields produced them? All we have to do is see which field, or fields, created those extremely rich individuals, and then we can connect that field to Gatsby. Since there are never too many fields that produce men of that much wealth, as our main character has, this should be fairly easy. There is one field that is known for getting rich because of fortunate circumstances rather than innovation on their part; gangsters during the 1920s, which is when Gatsby had all of his money and power.

Once Prohibition started in the 1920s, gangsters started to make insane amounts of money. That newfound wealth is why Al Capone is one of the most popular Americans ever. He ran the speakeasy business in Chicago. He sold alcohol underground and made more money through Prohibition than he ever could have made without it. You can tell people that they can’t drink, but you can’t prevent them from drinking, and in Capone’s case, buying the alcohol. Capone was so rich that he bought off cops and government officials to keep him alone. He gives them some of the money that he gets from alcohol, they look the other way, and the underground business continues to thrive. Everyone wins. And more disturbingly, Capone’s power continues to grow until the only way to get to him is through the one thing we all have to do; pay taxes.

So if Jay Gatsby was crazy wealthy, which the book clearly wants us to notice, there is a good chance that he was involved in crime since the richest men were criminals profiting from the underground alcohol industry during that time.

Not convinced that he was a gangster?

Okay. Let’s take a look at a few other things, and you’ll start to see that the character of Jay Gatsby is not the one that you thought you were reading.

  • He lies to the narrator – Every time Gatsby sees Nick, he says Old Sport in the same way that a gangster would repeat a line over and again to impress someone. There is always phoniness to a gangster in that regard. They pretend to like you since it is easier to communicate with someone in that repeated fashion. Just think of how we all pretend to be Italian gangsters when we say things like, “Forget about it.” This is similar to that. Part of the joke is that we know the guys are full of shit.

  • He gets pulled away for a mysterious reason – The book doesn’t say what it is that got him occupied, but early on, he gets told that he has a phone call. One that is clearly business in nature. Does he say that he is enjoying the party and that he will get to the job on Monday? No, instead, he gets up and addresses the problem. Is he a great businessman solving the problem during the weekend, or is he a criminal stopping a problem before it gets bigger?

  • He never talks business with the narrator – Nick Carraway likes Gatsby. He even feels bad for the guy, but the rich gangster is never interested in getting his new friend involved with his business. Perhaps there is a reason for that. The book tries to convey that the narrator sees something in Gatsby that others don’t, a trait that humanizes him. Carraway is right in this but is wrong in why many stay far away from our hero. Gatsby is a good man, in the same way, that Tony Soprano is a good man. He could be nice to you and may even say a few kind things about you, but he can also get someone to take care of you without a problem.

  • He has a large amount of alcohol at these parties – During the time when alcohol was illegal, Gatsby has parties with a ton of it. There is no way that this would be acceptable if Gatsby wasn’t a powerful and rich man during his day. He probably even bought off a few cops to allow him to have these parties. Something very similar to Capone’s actions than the book ever leads on.

If you start to put a few pieces together, you wonder what story Fitzgerald was really telling all along. –

A powerful gangster getting whacked.

Some questions are then posed if this is true:

  • Did Daisy know of his lifestyle?- Perhaps she found out about his criminal behavior, and that is why she left him. It was never that she didn’t love him. She knew that she couldn’t be with a man as dangerous as Gatsby. That may not be that far off, by the way. She wanted to have a normal life, with normal kids and not with a man in a field that produces so much crime. There is a side that has to ask if Daisy loved Gatsby so much, she probably wanted kids with him, but would she want kids with someone in a dangerous field like Gatsby? How many ladies out there would trade the wealthy gangster for a cheaper kinder man, one that their kids won’t be affected by crime? Probably many.

  • What is going on with that death? – If Gatsby is a gangster, a powerful one at that, then his death by the shooting of Wilson is not just some ordinary death. It isn’t a crime of passion like the book describes it, but more of a calculated hit on a powerful gangster. We are told that Wilson mistook Gatsby as the driver of the car, but what if Wilson knew that Gatsby wasn’t the driver and was going to kill him? He went to Gatsby’s house, which makes it appear that he only used the car to verify he was in the right place cause he was never looking for the person who killed his wife. He was looking for Gatsby.

  • What did Nick Carraway know? – Of course, we have to ask just how much the narrator even knew of all of this. Going by how he describes it all, he didn’t know that much of the whole thing. He is a naïve stranger presenting a story of a mysterious man he met one time, not a new acquaintance to the most popular, powerful man in the region. For all of his intrigue of the hero, he doesn’t ask the right questions concerning Gatsby’s true character. He is even dumb enough to go to his funeral, which no one attended, not because Gatsby wasn’t well-liked, but because people feared that they could be the next victim. Imagine how people would have felt if Capone got killed. Would anyone attend the funeral out of respect or avoid it out of fear? The narrator is so aloof; he thinks nothing of going to the funeral of the death that probably changed the power in the region he lived in. This is the key question since we are being presented the story by the man who doesn’t actually think this theory is possible. Basically, if you were to tell Nick Carraway that Jay Gatsby was a powerful gangster that he should avoid and that one day someone may kill Gatsby because of the crime world he lives in, Carraway would be shocked by it all; as if he never thought Gatsby was capable of such a life.

At the end of the novel, our hero, Gatsby, gets killed because a mechanic, Wilson, mistakes him as being the one that killed his wife. At least, that is what we are told. Remember, Carraway doesn’t think Gatsby is bad, so he has no reason to report his death as premeditated. Also, what type of person would work for the mafia, and how do they normally operate again? They have people have normal everyday jobs so they can hide in plain sight while running their criminal business. Everyday jobs – like a mechanic. There is a real possibility that Jay Gatsby’s death was not one of love but by a rival mob that planned on getting rid of him.

If you really want to have fun with this theory, then you can say that Owl Eyes was nothing more than someone spying on Gatsby. He was either an undercover cop checking up on the gangster or a part of another gang, trying to make sure that Gatsby was kept in check. He is the only guy that attended Gatsby’s funeral aside from Daisy and Nick, and it could be that he wanted to make sure that Gatsby was dead. Whether he was someone who wanted the hero dead is something for you to decide.

There is some level of awareness of Gatsby’s true position by the narrator once the rich man dies because the narrator doesn’t stick around. He leaves town. Now, he doesn’t say it is because he was afraid for his life, but with all we know of Gatsby now, you can view it like that too.

If I went to someone’s funeral and the only two other people there were his former lover and some stranger, I wouldn’t think it was because no one loved the guy or that no one wanted to attend. I’d be scared. Like, why is no one at this funeral? Who put the word out that they shouldn’t go? Someone as popular as Gatsby has to have someone go to his funeral, just for the hell of it. But to have no one is not a reflection of Gatsby’s popularity. No, someone doesn’t want anyone there. We are presented it as if no one loved Gatsby, who attended his parties, and that he lived a shallow life, which is why no one attended his funeral. But that makes little sense. There wasn’t one person who heard the news that attended his party once and thought, “Hey, I’ll stop by for a bit. That guy was pretty nice. I’ll pay my respects.” No. Everyone heard the news of Gatsby’s death and was told not to attend.

Jay Gatsby being a gangster changes the whole story we all know, but remember that his job is never defined set in stone. We are only told that he was very rich. And there is a lot of ways for someone to do that. If he was like most people who made mountains of cash, then he probably had to step on a bunch of people to get there, maybe even being a criminal himself, which makes his death even more intriguing.

Perhaps Gatsby was not lonely all along, and his happiness was never something he was concerned with, but rather he was paranoid for his own life. Maybe he didn't even love Daisy anymore but knew that his dangerous life could not only catch up to him but her as well.

This is one of those theories that just seems to never end. It is like I read a completely different book.


Did You Know?

The Great Gatsby sold no more than 25,000 copies in Fitzgerald's lifetime. Today it has sold more than 25 million copies.



Hey readers,

We hoped that you liked this theory and would love to hear some of your thoughts on it. It's like we only reached the tip of the iceberg with this one.

Follow us on social media.

Subscribe to our blog if you want to receive the weekly newsletter.

Thanks for reading.


If you do like this post, please share this on social media. It means a lot to us. Thanks.


Read more


Check These Out


Follow This Blog On Social Media


About The Blogger

Greg Luti is an editor and blogger on His favorite writers are Robert Frost and Charles Bukowski. He enjoys reading up on history, watching comedies, and playing video games, when he is not writing down a few notes for his next piece. He started this blog out of his love for literature and hopes that the reader shares that same passion.


Learn More Of The Blogger



bottom of page