I don’t gamble. At best, I’d play a slot machine if one presented itself to me. I like the idea of putting something in and many things potentially coming out, accompanied by the chaotic sounds of metal striking metal. But today’s machines operate through computerized cards. They feel unsensual. Abstract. Abstract money, abstract rewards, abstract loss. Like betting on whatever you can now bet on in life—a sports player’s performance, the weather, political events, the valuation of some company—through an app.
I also don’t have an investment portfolio. More like money stashed in a mattress. “You’re not even keeping up with inflation,” I’ve been admonished. Call me old fashioned. Call me a woman in a man’s world. Whatever this makes me, it leaves me outside one of the deepest currents in American life.
According to the American Gambling Association, $166.94 billion in wagers were placed in legal sports betting in 2025, with illegal betting of all types estimated at $511 billion annually. We all know Elon Musk was recently named the first trillionaire for the valuation of Space X, which I kept saying was a billion million, or maybe a million billion, but it turns out it’s a million million, though by then numbers cease to make any sense. Wouldn’t I be the best gambler?
David Bockino, in his new book Over/Under: An Unexpected History of Sports Betting, claims that betting is the lifeblood of the United States. Contrary to how some puritans would have it, he sees the country’s ascent as inextricable from a world of con-men, hustlers, bookies, speculators, and mob rings who created our American brand of sports, all for the very purposes of betting.
After weeks of celebrating the Knicks and watching the wild fandom pour out from Madison Square Garden, it was surprising to read Bockino’s history of “The World’s Most Famous Arena.” MSG opened in 1879 with crowds betting on something called pedestrianism, in which people would walk, run, and even crawl, in a circle until they collapsed, usually for up to six days. There was some justification that doctors could study human endurance through these competitions, and that it was no different from learning about breeding horses for horse racing.
One ought to remember that animals play a large role in the origins of betting—a cruelty that knows no bounds—with New Yorkers seemingly fascinated by competitions between rats and dogs, ostriches, and even bears. How many rats can a dog kill in an hour and for how long? Gathering rodents for these morbid competitions was one among many jobs this world created. Speculation, at least in these early Gladiator-like American renditions, was speculation on life and death.
Laws and the regulation of gambling, especially around sports, were instituted little by little in the U.S., beginning in the 1950s. Then in 2018, we legalized betting, seemingly less because we think it’s a good idea, and more because the Internet is hard to regulate and we like giving favors to technocrats. Perhaps legalization acknowledged what the digital already was: a place where everything is a potential market and uncertainty is an asset. Zuckerberg’s Meta is trying to partner with Polymarket and Kalshi. Maybe, just maybe, the jig is up and the whole world is, and always has been and will be, our casino.
What is this about unconsciously? In his 1957 bestseller The Psychology of Gambling, Edmund Bergler, one of the few psychoanalysts eccentric enough to write on gambling, says it’s unconscious masochism. We want to lose, we want to hit rock bottom, we are begging for castration (some form of law to appear and hold us to account), and we are deeply guilt-ridden for what we have gained over and against others, even if it was only the wish to do so and not even a reality. We are, as Freud called us, criminals out of a sense of guilt.
Guilt—at least in this sense—comes from a failed collective. Without a social contract, punitive omnipotent wishes flourish for which we must be punished. For Bergler, our poor unconscious masochists are stuck playing out a monotonous masochistic drama in which:
- The psychic masochist unconsciously provokes or misuses situations in which he is defeated, rejected, and denied.
- Unaware that he himself has been responsible for these defeats and rejections he strikes out in righteous indignation, and apparently in self-defense, against the world’s cruelty and injustice.
- Then follows profound self-pity; fate has handed him a raw-deal.
The gambler, says Bergler, is the best example of this neurotic problem, though by no means the only form of sado-masochism available to us. So where will a nation of injustice-collectors who bet-the-farm to relish their need for self-sanctioned, self-righteous defeat go? I called my friend Jay Bulger, a documentary filmmaker, writer, and the founder of the Bronx Legends boxing gym and academy, to read the tea leaves with me. He recently tackled gambling for New York magazine, following the conviction of his friend, Tim McCormack, for a fixed bet involving NBA player Jontay Porter—both life-long gambling addicts.
Jay, I’m excited to talk to you about the state of sports betting, which I never thought I’d be so exposed to.
Gambling is rampant. Fifty-one percent of all men ages 18 to 35 gamble. I keep having this argument over whether illegal is worse than legal. The DraftKings guy kept saying to me, “Isn’t it great that this isn’t taking place in the underground gambling casinos?” I was like, “Yeah, but at least there was somewhat of a barrier to entry before.” You needed to know a bookie. You needed to know underground figures to place a bet. Now you’re given the vaping equivalent of gambling.
The collusion between so many different entities that have come together to make this gambling industry seems unstoppable. Sports are so powerful. You’re talking about—second to religion—the most important facet of the lives of Americans. Gambling apps are now threaded throughout sports programming, and they’re also the sponsor. More importantly, you have announcers telling the viewer what the change in the gambling stats are and the line. Will there be class action lawsuits that will rectify this obviously corrupt situation given that people are just being force-fed gambling?
When they legalized gambling, apps were developed where you can now bet on anything: Polymarket, Kalshi, FanDuel, DraftKings.
You can bet on anything, and it’s very hard to track. You had the White Sox lose the World Series. Maybe you go back and you look at that whole game and you’re like, “Whoa, these guys were intentionally dropping balls,” or whatever. But now you can gamble on something as specific as a player getting less than five rebounds. How do you watch a game knowing that? It seems very easy to cheat now, or to be involved with the cheating, since this player can just get four rebounds and not get the fifth, and he and all his friends can make money.
That’s where you end the New York magazine article, saying that there’s no way that these apps can check all these small bets. On top of that, the players have always been involved in score fixing because everyone’s cashing in on them.
This is what happened with the Jontay Porter scandal. The number one bet of the day was this random replacement sixth player on the team that wasn’t necessarily even gonna start the game, and then he’s starting the game and all of a sudden all these people are gambling against him. It was obvious. Contrary to what the betting app spokesman claimed, what I found was that there were so many people who got away with the bets and weren’t caught. And even more interesting was that the impulse of the degenerate gamblers participating in a fixed outcome felt to them so different from their usual rush. I kept asking them about it because after they won, they immediately lost all their money on blackjack. The main addiction is to losing.
That’s the high that really puts you back into reality. It’s like, Okay, now I’m back. I don’t have any money. I’m me and I’m able to get the money to do that again. After you get money, there’s certainly some escapism and fantasy of upward mobility. But I just don’t know too many successful gamblers. I wish I did.
Trump is a successful gambler. Are we greedy puritans?
I happen to have grown up Catholic. I think that we 100 percent want to be punished.
I think about how weird we are about drinking. You can buy a gun and vote here before you’re allowed to legally drink. And everyone drinks to excess in this country. That doesn’t happen in Europe. All laws incite transgression. Once you draw a line, you understand what it means to cross it. So how do you help everyone care a little bit about the rules together, rules we need to be able to live by, like the prohibition against murder? Legalization as you describe it, is not that sensibility. It’s not a liberalization that allows us to balance our relationship to something. It comes on the heels of something having been illegal, then creating and fueling a market for it in excess. Still, all the guilt and bottoming out is on the individual.
There need to be some safeguards. I don’t know what’s possible. They have UFC fights on the lawn of the White House. We’re combining armies with Israel, as opposed to distancing ourselves. And everyone is gambling. You can’t not gamble. And it’s just gonna get worse and worse and worse. If you can bet on whether the next pitch is gonna be a ball or a strike, you can’t regulate baseball at all. It just takes one pitcher scratching his head for his friend who is at home gambling to get the signal. Objectively, I just don’t see how you regulate that.
The people in my New York magazine story are gamblers of the highest degree, lifelong gamblers. Millions of dollars coming in and out. And it’s really irrelevant whether they won or lost. It’s all about losing and then the scramble to figure out how to get it back.
The psychoanalyst who wrote about gambling, Bergler, was interested in this kind of gambler because they obviate a chase for a strange, uncanny feeling of pain-pleasure in pure loss. So if over 50 percent of young men are gambling, what do these extreme gamblers tell us about what’s going on more broadly? If the idea is that you want to lose everything, that’s a doozy of a diagnosis.
We don’t have a middle class, right? We basically have a bunch of poor people and a bunch of rich people. Is there not something to be said about this being another way to just keep people poor? It’s escapism, the fantasy of getting out of something by way of an easy shortcut. No different than the lottery, except maybe you feel like there’s more intelligence involved, even when there isn’t, because it’s a scam. The house always wins. I never gamble, but I gambled on Saturday as a preface to this conversation.
Did you win?
Yeah, I won a thousand bucks. Why did I do it? Because just like these guys, I knew the outcome. UFC is not my sport, but I had the pleasure of spending some time with Conor McGregor. He was shooting a commercial three weeks ago for Polymarket. I’m there watching the thing, and I’m like, I’m gonna bet against this guy. Why? Because he should be training, and instead he’s making a gambling commercial. Lo and behold, the fight only lasted 20 seconds, because he had blown out his knee. Of course, the odds did not represent the reality of the situation. People are very swept up in legacy and fame and people want someone to be something that usually they’re not. A lot of times the odds are just not indicative of reality.
Even if we consciously bet on a fantasy, we may unconsciously beg for reality to set us straight. What feels more obvious now is that we only further isolate people. It’s your addiction, it’s your crime, versus the idea that we’ve created a system which enables addiction and that incentivizes crime.
I just visited Tim McCormack from my article in prison. He swears he’s not going to gamble anymore. But his friends were like, “He’ll be back.” It’s like vaping as opposed to cigarettes. Now, with cigarettes, you’ve got to go find some smoking corner to go do it. It’s naughtier than ever. But with vaping you can do it all the time, anywhere. It’s limitless.
I always think about my dad and how violent it was to listen to him watching sports. His relationship with the TV on Sunday was so unhealthy. We just kind of stayed away because he would be like, “He missed it! ARGHHHH.” I was like, “Holy shit!” I can only imagine what he would have been like if gambling was on top of it.
I always think about how we have these sports teams and at the end of the day they’re corporations that have nothing to do with where they’re based, except for the financial decisions that a corporation has made to obtain players, yet we think they somehow represent us. I was very inspired to figure out why people would be obsessed with sports to the extent that they would trash their life savings and take that roller coaster. The class action lawsuits are going to be wild because they’re going to show that behind closed doors all these entities came together knowing that it’s unhealthy and we still allowed it.
This is the problem with the apps. We’ve been given devices and are told that we have to regulate our relationship to them, but they are designed to be unregulatable. Humans are not capable of moderation. That was a basic Freudian premise, that we go over the line. There are ways of going over the line that are creative and productive, maybe risky, but that have positive, or at least interesting outcomes, versus being on your phone all the time, or vaping, or gambling. We fuel these dreams of becoming a billionaire, but we’re actually impoverishing the majority of our citizens. You talked about how these gamblers get a status on FanDuel inciting more and more fantasy.
I challenged the guy from the betting app: I was like, “Come on, man, you won’t admit that you incentivize degenerate behavior, like when the guy ran out of money, you sent him on a gambling cruise.” A gambling cruise is crazy. You can’t even leave the fucking casino. It’s like the absolute antithesis of rehab.
But isn’t that America? Aren’t we stuck on a gambling cruise?
It seems like that’s where we’re headed, for sure, which is why I created the boxing gym. My greatest theory about creating the boxing gym was that as we become so reliant on the digital technological world coming together in real life is that much more important.
We were talking about the high that a lot of the gamblers said that they get as they start to lose. You don’t really know what weird trance you’re in when you’re winning, and you don’t even know what strange enjoyment you’re getting out of losing. In the boxing gym…
You get punched in the face if you don’t put in the work. It’s super straightforward. The risk versus reward. It worked for me, you know, and I think that as kids become more and more ADHD you need something that forces you to focus, like I need to focus or I’m going to get punched in the face. It’s for people that are extreme, like me, who need to take extreme measures to get in shape. Maybe it’s gambling with your cerebral functionality.
It’s physical. It’s sensual. It takes discipline. You have a sense for the work you put in. Of course, there’s a lot of adrenaline in it. There’s a high risk-reward ratio, but nevertheless, it’s real. The gambling article complements not only your work with the new boxing academy but also your writing about marijuana and your long history of running a weed delivery service. You say that legalization is the point where real degradation begins. Of course we want to stop criminalizing drugs, poor people, people mostly of color, for selling weed. But just because we never should have done that to begin with, doesn’t mean we celebrate a legalization process that is a total degeneration by creating a market. You say there’s no quality or care around it at that point.
I still get my weed from the black market, and I don’t see a future where I will be buying it at a store. The reason being that the constraints that they put on the market make it impossible to actually grow good weed. In the same way that it’s really hard to get people fresh orange juice. Business capitalism will always go in the direction of the highest profit margin. The weed that I like to smoke and the juice that I like to drink is organic and as good as it gets which is hard to get. A good way of looking at what’s going on with gambling is that the apps are fentanyl. Fentanyl is that much stronger: it’s synthetic, easy, and lethal. A lot of these people are chasing that, you know? You want to come as close as you can to death.
That would be the psychoanalytic message, which is that you have internalized that your life isn’t worth much, and you’re better off dead. No one’s going to take care of you. And so even as you chase a fantasy of getting out that is near impossible realistically, you actually end up chasing the most real thing which is exactly what this world serves you, namely death. You only realize it when you lose it all.
For further study…
- Jay Bulger on the legalization of marijuana
- The philosophical gambler, Blaise Pascal, on wagering on the afterlife
- David Graeber on his book Debt: The First 5000 Years
- Freud on the gambling (masturbating) Dostoevsky
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