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What Up Holmes?

October 24, 2025

AI Summary

5 min read

What Up Holmes?

In 1919, Oliver Wendell Holmes—widely regarded as the greatest Supreme Court justice in American history—wrote a dissent that would become the foundation of modern free speech law. The problem is that just eight months earlier, Holmes had written the exact opposite. He had authored three majority opinions upholding prison sentences for people who criticized World War I, dismissing their First Amendment claims with something close to contempt. Then, in November of that same year, he switched sides. He wrote that "we should be eternally vigilant against attempts to check the expression of opinions that we loathe." He gave us the metaphor that still props up American free speech: the marketplace of ideas.

The question that has haunted legal historians ever since is what made him change his mind.

The soldier and the censor

To understand the magnitude of the shift, you have to understand who Holmes was before it. He came from a wealthy Boston family and fought for the Union in the Civil War. The experience marked him permanently. He watched most of the officers in his regiment die at Gettysburg. He nearly died himself. He kept his blood-stained uniform hanging in his closet for decades afterward. That war forged his worldview: when people were risking their lives on the battlefield, it was not too much to ask people at home to support them.

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What you'll learn

  • 1 (01:46) **Introduction: The Origin of the Marketplace of Ideas** - Latif introduces the episode, framing the modern debate over free speech online as stemming from a single historical moment and a single man: Supreme Court Justice Oliver Wendell Holmes.
  • 2 (03:07) **The Anti-Free Speech Justice** - Holmes is introduced as a towering figure who was initially stridently against free speech as we know it.
  • 3 (04:15) **World War I and the Espionage Act** - The context for Holmes's early anti-speech rulings: WWI and the 1917 Espionage Act.
  • 4 (05:58) **Holmes's Civil War Roots** - The source of Holmes's initial anti-speech stance: his traumatic experience fighting in the Civil War.
  • 5 (08:24) **The Great 180: The Abrams Dissent** - Eight months later, in the Abrams case, Holmes completely switches sides, writing a passionate dissent defending free speech.
  • 6 (10:00) **The Mystery: What Up Holmes?** - Thomas Healy becomes obsessed with the question of why Holmes changed his mind, reconstructing his life day-by-day for a year and a half.
  • 7 (11:05) **The House of Truth** - Healy discovers Holmes became close with a group of young progressive intellectuals in Washington D.C.

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Show Notes

Love it or hate it, the freedom to say obnoxious and subversive things is the quintessence of what makes America America. But our say-almost-anything approach to free speech is actually relatively recent, and you can trace it back to one guy: a Supreme Court justice named Oliver Wendell Holmes. Even weirder, you can trace it back to one seemingly ordinary eight-month period in Holmes’s life when he seems to have done a logical U-turn on what should be say-able.  Why he changed his mind during those eight months is one of the greatest mysteries in the history of the Supreme Court. (Spoiler: the answer involves anarchists, a house of truth, and a cry for help from a dear friend.)  Join us in an episode we originally released in 2021, as we investigate why he changed his mind, how that made the country change its mind, and whether it’s now time to change our minds again.

Special thanks to Jenny Lawton, Soren Shade, Kelsey Padgett, Mahyad Tousi and Soroush Vosughi.

LATERAL CUTS:
Content Warning
Facebook Supreme Court
The Trust Engineers

EPISODE CREDITS: 
Reported by - Latif Nasser
Produced by - Sarah Qari
with help from - Anisa Vietze

 

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