Critics at Large | The New Yorker

Episode: Why We're All In on Gambling

Date: September 11, 2025
Hosts: Vinson Cunningham, Naomi Fry, Alexandra Schwartz

Brief Overview

In this lively and incisive episode, the Critics at Large trio—Vinson Cunningham, Naomi Fry, and Alexandra Schwartz—explore the widespread and growing integration of gambling into modern American life. They dissect the mainstreaming of sports betting, the emergence of platforms like Polymarket, and examine why, in a time of social instability and uncertainty, so many people are drawn to risk it all. Drawing from literature, film, and their own experiences, they tackle the allure, dangers, and cultural implications of gambling's dizzying boom.

Key Discussion Points & Insights

Personal Histories and the Ubiquity of Gambling

[01:00–02:54]

• Hosts’ relationships with gambling:
  • Naomi avoids it for fear she’d “never stop.”

    "If I start, I won't stop. Or that's at least the fear that I have deep within me." – Nomi Fry [01:17]

  • Vinson recalls his religious upbringing where gambling was taboo, yet describes the recent thrill of betting on horses.

    "No smoking, no drinking, no gambling. I don't know why gambling got in there, but it was like a big thing." – Vinson Cunningham [01:41] "It was worth it to watch those majestic beasts run... The money just made everything matter more. And I was like, oh, no, I get it." – Vinson Cunningham [02:28]

  • Alex lost $20 in a shell game and was “done in five seconds.”

    "I once lost $20 in a shell game. And that was it for me." – Alex Schwartz [02:54]

Gambling Goes Mainstream—Sports Betting & Polymarket

[03:27–06:08]

• Naomi describes surprise at discovering Polymarket, a site allowing bets on everything from global events to who’ll succeed Anna Wintour at Vogue.
  • The normalization of gambling beyond casinos: “Suddenly everything is up for grabs... it's just regular people.” – Nomi Fry [03:38]
• Alex summarizes changes in regulation: 39 states now offer legal betting, 32 online, after the 2018 Supreme Court decision overturned federal restrictions. [09:23]
• Vinson notes the onslaught of gambling ads during sports events:

  “Even in the spaces where it belongs, it's a bigger part of the narrative than it has ever been before.” – Vinson Cunningham [05:25]

How Gambling Has Changed the Sports Fan Experience

[07:42–11:09]

• Vinson discusses the drastic shift in watching football:
  • Constant betting odds banners, segment picks on talk shows, and promo codes. The game often serves as a pretext for betting narratives.

    "The game is a pretext for the sort of monetary fortunes of small time bettors everywhere... The game becomes this odd secondary show." – Vinson Cunningham [08:28]

• Rise of “props” and “parlays”—bets layered on everything from the national anthem length at the Super Bowl to an individual’s rebounds. [11:20]
• Personal stories about the way betting emotionally affects players:
  • Athletes, like Kevin Durant, joke about their performances ruining fans' parlays.

    "Watches when people get mad at him during games because of the parlays and says, here's one tweet: 'when them parlays don't hit.' … I'm grateful I have this much power now." – Vinson Cunningham [10:24]

  • Nomi: Pro athletes get harassing DMs from fans whose bets they’ve ruined.

    "The ire that they feel because their bets didn't hit based on this guy's performance... it's scary." – Nomi Fry [12:37]

• A sense that the experience is more privatised and less communal than before—sports are now consumed “with individual interests in mind." – Vinson Cunningham [14:28]

The Enduring Drama of Gambling in Art and Literature

[19:29–31:19]

• The hosts reference key gambling texts that frame high stakes as metaphors for life:
  • George Eliot’s Daniel Deronda: Opens at a roulette table, gambling as a metaphor for life choices.

    "...she is determining the plot of her life and the choice that she makes is kind of a gamble, right?... one of the things that attracts us about gambling is it's... symbolic of metaphorical qualities..." – Nomi Fry [20:23]

  • Colson Whitehead’s The Noble Hustle: About entering the World Series of Poker; gambling as self-examination.

    "I have a good poker face because I am half dead inside." – Colson Whitehead (read by Vinson Cunningham) [23:44]

  • Tolstoy’s War and Peace: The agony and fascination of Nikolai losing at cards, illustrated with vivid bodily focus and loss.

    "Those hands which he loved and hated held him in their power." – Alex Schwartz quoting Tolstoy [27:55]

  • The Sopranos / Uncut Gems: Portraits of crushing addiction and compulsion; harrowing yet gripping.

    "Watching someone lose and do so at high cost at a sort of spectacular level of sort of adrenal energy... addicting about that." – Vinson Cunningham [29:36] "You get invested and you get involved and you live that high of hope and expectation that the next bet is the one that's going to change it all. Because of course it could." – Alex Schwartz [31:19]

  • The Big Short: The thrill of winning big at the expense of others.

    “We just made the deal of our lifetimes. We should celebrate.”—Line from The Big Short, quoted [32:48] “And then you remember that their benefit is the detriment of millions…” – Alex Schwartz [32:46]

Polymarket & The Myth of Expertise

[35:10–41:31]

• Exploration of Polymarket as a platform for betting on real-world events.
  • "It's all yes/no bets... for someone who wants to place a bet, you can just scroll around and place a bet on Israel withdraws from Gaza in 2025. Let's take a crack at it and see if you make any money, folks." – Alex Schwartz [37:40]
• The site’s “accuracy” and how people believe betting with real money makes predictions more honest than polls.
  • "This can give you a kind of more accurate bellwether. I think that's an illusion, but it's a really compelling illusion." – Alex Schwartz [38:48]
• The danger of self-anointed expertise, and democratizing risk without safety nets.

  "...it's a Wild west situation... some people have gained much. Many more people have lost a lot, you know, and like anything else in this country, like, there's really no safety net." – Nomi Fry [40:44] "I just feel something very, very predatory in this encouragement of everyone to consider themselves an expert." – Alex Schwartz [41:31]

Gambling, Control, and Canceling Uncertainty

[42:29–49:25]

• Vinson connects the cult of “mindset” and self-expertise back to financialization, “If only you would bet on yourself…” [42:29]
• Nomi likens dating-app behavior to gambling: individuals become gamblers in the unpredictable game of love. [44:43]
• Vinson observes how algorithmic, app-based gambling dehumanizes both bettor and subject, paralleling the digitization and atomization of modern life.

  "...the impulse to gambling, at least of this kind, the app based algorithmic gambling... is a way not to deal with the other and treat them as a separate being from oneself." – Vinson Cunningham [44:47]

• The link between the thrill-seeking culture and a withdrawal of social or religious guardrails:

  "We live in a culture... that loves gratification and the delivery of gratification... there's more benefit, there's more profit, and not to us, by removing those guardrails." – Alex Schwartz [46:38]

• Why people may gamble when the world feels uncontrollable—asserting agency when systems fail.

  "If I can't stop a war, if events around me seem totally chaotic and unresponsive to the usual levers of control, what can I do except ride the rollercoaster of speculation...?" – Vinson Cunningham [48:01]

Notable Quotes & Memorable Moments

• On the psychological core of gambling:

  "Gambling is such a big theme in literature... because it comes back to this fundamental question that everyone has about themselves, which is, do I got it or don't I?" – Alex Schwartz [25:31]

• On gambling’s transformation:

  "The degenerate aspect has actually faded and now the gambler is cleaned up. He or she is just like you or me, sitting watching the sports game, thinking, you know more about it than everybody else." – Alex Schwartz [35:23]

• Summing up the temptation:

  "You want young person of whatever orientation, you want to feel a real rush, go up to a real person and tell them, hey, I like the cut of your jib. Could I get your number? That is the biggest high." – Vinson Cunningham [48:00]

• On self-destruction and lost restraint:

  "Don't drink, don't smoke, don't gamble, basically, don't destroy yourself is what I hear from that." – Alex Schwartz [46:38]

• On false empowerment:

  "The only thing separating you from the expert, better the expert investor... The only difference is, as they say, a mindset." – Vinson Cunningham [42:29]

Timestamps for Important Segments

• [01:00] Cohosts’ personal experiences with gambling
• [03:38] The surprise of Polymarket and gambling on “everything”
• [07:42] How online betting transformed football viewing
• [09:23] Gambling legalization and regulation context
• [11:09] How betting impacts athletes and fans
• [20:23] Gambling as literary and metaphorical device—Daniel Deronda
• [23:44] Colson Whitehead and “betting on oneself” vs. others
• [27:55] The agony and spectacle of losing in War and Peace, The Sopranos, Uncut Gems
• [32:46] The Big Short—profiting from catastrophe
• [35:10] Polymarket as the new face of betting and pseudo-expertise
• [42:29] The cult of self-empowerment, “mindset,” and predatory systems
• [44:47] Dating, dehumanization, and “spreadsheet love”
• [48:01] Gambling as a (false) bid for control amidst societal chaos
• [49:25] Final reflections: real-life risk, thrill, and caution

Conclusion

The episode’s tone is witty, probing, and just a touch world-weary. The hosts alternately marvel at and recoil from gambling’s seductive logic and its insidious entrance into all realms of public and private life. They weave together cultural references, personal anecdotes, and sharp critique, ultimately suggesting that while gambling offers the mirage of control and excitement amidst uncertainty, it exacts a psychic and, often, material cost—one that our current moment seems especially susceptible to.

If you or someone you know is struggling with a gambling problem, help is available at the National Problem Gambling Helpline: 1-800-GAMBLER.