Freakonomics Radio — Episode 662: "If You’re Not Cheating, You’re Not Trying"

Date: February 6, 2026
Host: Stephen J. Dubner
Guests: Floyd Landis, Louisa Thomas, April Henning, Aaron D’Souza

Episode Overview

This thought-provoking episode explores the evolving meaning of "cheating"—specifically in the world of sports, but with broad implications for society’s relationship with rules, morality, and technological enhancement. Stephen Dubner traces the arc from strict rule-following to deliberate rule-bending: from the lessons sports can teach us about fairness, to notorious doping scandals, to the audacious vision of “Enhanced Games”—an Olympics where performance-enhancing drugs are not only permitted, but celebrated. What actually counts as cheating, who decides, and how do these binaries shape culture far beyond the playing field?

Key Discussion Points & Insights

1. Why Cheating Feels Ubiquitous—and Why Sports Might Be Different

• [00:00–05:32]
  • Dubner frames the discussion by observing that many people have lost faith in society’s rules, seeing them as arbitrary: “My belief is that many people in many different circumstances have come to think that the rules we live by are stupid … so stupid that the only sensible thing to do is break them.”
  • Louisa Thomas (The New Yorker) draws a parallel between “Alice in Wonderland”—where arbitrary and capricious rules frustrate Alice—and real-life sports. She argues sports let us practice living within rules:
    • “The rules need to be fair. They need to be consistent. What would a proper croquet game look like?” [03:57]
    • Sports acts as “practice for society”: teaching us to tolerate injustice, work together, win and lose gracefully.
  • Dubner: “Theoretically, what you’re describing is also supposed to apply to society generally.” [04:38]

2. Cheating, Enhancement, and the Evolution of Sporting Rules

• [05:32–23:00]
  • Cannabis use by athletes is discussed as an example of shifting rule boundaries.
    • Floyd Landis (former cyclist): “Something that I found was beneficial to me and helped me perform and make everyone money and make everyone happy. It was something that I hid. It's like I turned into, like, a criminal and a drug addict.” [05:50]
  • Introduction of the central subject: the persistent, complicated dance between athletes, rules, and “innovation”—most iconically in doping.

3. The Floyd Landis Story: From Rural Outsider to Vilified ‘Cheater’

• [07:14–43:14]
  • Early Life and Ascent
    • Grew up Mennonite in rural Pennsylvania; cycling became escape and obsession.
    • Family was supportive but wary; he rose quickly, won the junior national championship; “A lot of these things are just chance.”
  • Joining the U.S. Postal Service Cycling Team
    • Became close with Lance Armstrong, stepping into world of elite cycling and its pressures.
    • Landis describes the team’s doping regimen with details: EPO, blood transfusions, “gaming the system” [13:07–15:36].
    • The system was open and widespread—“Pretty much all the top teams … it was openly talked about, you know, within the sport.” [15:42]
    • “People like to call it cheating. You can call it that. I’m not sure who was cheated, but that's just what it was.” [16:04]
  • Winning the Tour and the Scandal
    • Won the Tour de France in 2006, was quickly accused and stripped of victory.
    • Landis recounts his denial, shame, and eventual psychological spiral: “Three weeks after the tour ended, I had my hip replaced ... I drank way too much, and I just checked out. I couldn't face it.” [20:49]
    • Regret for not coming clean immediately: “If I had another season of having won the Tour, I would have had all of that, but I just didn't have anybody that could advise me on what to do. I don't know if anybody would have known what to do. We got this positive test. You’re guilty. What are you going to say?” [17:51]
    • Dilemma: If he confessed, he would implicate friends and end any chance of racing again; so he denied, wrote a (dishonest) book: “I sound like an idiot, but that’s what it felt like at the time … it was wrong.” [20:02]

4. A Brief History of Doping and Anti-Doping Policy

• [24:54–31:50]
  • April Henning (sport sociologist) situates doping in a long, complex history.
    • Performance enhancement spans from the Ancient Greeks to today.
    • Defining “performance enhancing drug” is tricky; the lines between caffeine, electrolyte gels, or steroids are cultural as much as scientific.
    • Mythmaking and media have often painted doping as the culprit for tragedies, even without evidence (e.g., Jensen's 1960 death at Rome Olympics).
    • WADA’s list of banned substances: “It poses a health risk, it enhances performance, or it violates, quote, ‘the spirit of sport.’” [28:50]
    • Cautions against binaries like “natural vs. artificial”: “One of the things that lots of people try to do is break down between natural and artificial. And I think that's really a trap.” [31:06]

5. Landis's Whistleblowing & Systemic Complicity

• [32:11–43:14]

  • After years of inner torment, Landis blew the whistle, first emailing cycling officials, then working with USADA and federal agents.

  • Systematic complicity: “The CEO of USA Cycling, everybody at the organization … knew this was what was happening. All of them acted like I was the bad guy and washed their hands of it.” [32:37]

  • USADA focused narrowly on catching Armstrong, not on fixing deeper institutional rot.

  • Landis: “If you can't face the fact that the organization that runs the whole thing is in on it, then you didn’t fix anything.” [36:47]

  • Public fallout, lawsuits, and Armstrong’s eventual confession followed.

  • Landis on Armstrong: “I empathize with him on how badly he's been beaten down. And it sucks. It's awful. And he's a human. In the end, I don't wish any harm on him.” [39:33]

  • Personal rebuilding: Launched a nutritional and CBD business, “Floyd’s of Leadville.” Wrestling with difference between character and reputation, parental forgiveness, and regret.

    • “If you have the drive and the obsession with being a professional athlete, you kind of do care what people think ... at the end of the day, when you lay down at night and go to sleep, it’s just you.” [41:17]

6. Introducing the ‘Enhanced Games’: Cheating Becomes the Norm?

• [43:14–55:00]
  • Aaron D’Souza (entrepreneur): Enhanced Games, a new “Olympics” where performance-enhancing drugs are allowed, is set for Las Vegas in May.
    • “The Enhanced Games are a new version of the Olympics, but we allow performance-enhancing drugs and we pay all athletes.” [45:44]
    • Three athlete categories: natural, self-enhanced (private doctor), or under clinical trial (monitored by UAE regulators).
    • Massive financial incentives, including $1 million bonuses for world records.
    • Backed by major figures like Peter Thiel and Donald Trump Jr.’s firm.
    • Framed as both sporting event and biotech marketplace: “The end conclusion ... is not a sporting event, but it's actually curing aging ... Only one of them needs to succeed. It will be worth a trillion dollars.” [50:52]
  • Traditional authorities (IOC, WADA) view Enhanced Games as “irresponsible and immoral.”
  • D’Souza focuses on consent and productivity: “I’d be very happy to have a brain computer interface implanted because I think that would be a very productive use of technology.” [57:37]

7. What Happens if Cheating is No Longer Cheating?

• [53:03–56:25]
  • Landis is skeptical Enhanced Games will break Olympic records: “What will happen … no records will be broken. Then they have a dilemma. Either the drugs don’t work or … everybody’s already on them.” [53:23]
  • Henning: The major social achievement of anti-doping has been making doping a moral taboo—less about health, more about defining “good” and “bad” people. [53:45]
  • She sees value in some banned substances as medicines, and critiques the binary, moralistic language (“clean” vs. “dirty” athletes).
  • Big question: “Sport sets up a moral framework for how we should be. It's a phenomenon bound by rules. Rules are what make it what it is. And if those rules aren't consistently applied, then the sport ceases to make any sense.” [54:12]

Notable Quotes & Memorable Moments

• Stephen Dubner: “Many people … have come to think the rules we live by are stupid. So stupid that the only sensible thing to do is break them.” [00:33]
• Louisa Thomas: “Life is more like the croquet game with the flamingo as a mallet and the hedgehog as a ball. We have to figure out some way of making our way through this totally arbitrary and capricious world.” [04:00]
• Floyd Landis: “People like to call it cheating. You can call it that. I’m not sure who was cheated, but that’s just what it was.” [16:04]
• “I was not breaking the rules. So I decided that, okay, I have to fight this thing, and I have to at least tell a story that is believable so that I can try to get back and race. I sound like an idiot, but that's what it felt like at the time.” [20:02]
• April Henning: “One of the things that lots of people try to do is break down between natural and artificial. And I think that's really a trap.” [31:06]
• Aaron D’Souza: “My goal is to bring about the 10th age of mankind, the enhanced age, where everyone has the opportunity to become enhanced.” [46:14]
• “The end conclusion of the Enhanced Games is not a sporting event, but it's actually curing aging … literal superpowers.” [50:52]
• Landis on Enhanced Games: “No records will be broken. Then they have a dilemma. Either the drugs don’t work or … everybody’s already on them and they don’t want to face that.” [53:23]
• April Henning: “Sport sets up a moral framework for how we should be. It's a phenomenon bound by rules.” [54:12]

Important Timeline Timestamps

• 00:33: Dubner introduces the idea of weakened faith in rules.
• 02:24–05:32: Louisa Thomas’s allegory from “Alice in Wonderland” to sports and society.
• 05:50–06:32: Example: cannabis use going from disqualifying to ignored in sports.
• 07:44–21:20: Floyd Landis’s journey through cycling, doping, scandal, and regret.
• 24:54–31:50: April Henning traces doping history, shifting definitions, cultural baggage.
• 32:11–43:14: Landis's whistleblowing and the aftermath.
• 45:44–53:39: Aaron D’Souza outlines the Enhanced Games; his vision and controversies.
• 53:45–56:25: Doping as a moral taboo, Enhanced Games’ implications for the definition of cheating and sporting rules.
• 56:25–End: Tease for next episode, focusing on changing societal rules and the story of Ricky Williams.

Tone and Language

The episode is rich with personal candor (especially from Landis), analytic caution (Henning), and a provocative, almost sci-fi futurism (D’Souza). The tone is at turns confessional, skeptical, philosophical, and slightly irreverent—true to Freakonomics’ brand for highlighting the “hidden side of everything.”

TL;DR

This episode interrogates what “cheating” truly means, focusing on drugs-in-sport but probing complexities that blur into society as a whole. Through Floyd Landis’s personal reckoning, April Henning’s scholarship, and Aaron D’Souza’s radical “Enhanced Games” proposal, listeners are challenged to reconsider the shifting lines between rules, morality, innovation, and what we truly value about fairness.