The Structure of Ideas
Mapping a New Theory of Free Expression in the AI Era
Jared Schroeder



Mollie Steimer refused to stand. Everyone else rose from their seats as New York Court of Appeals Justice Bartow Weeks entered the courtroom. Steimer remained seated. Others in the courtroom urged the young woman to stand. Some might have thought Steimer didn’t know the decorum, but the twenty-two-year-old Russian immigrant was well acquainted with courtrooms. She spent about ten days in federal court during a trial a year earlier in October 1918. Steimer and five others were convicted of violating the Espionage Act after they dropped thousands of leaflets that criticized the president and US foreign policy toward Russia from a New York City building.1 The New York Tribune, during its coverage of the final day of her federal trial, described Steimer as “a tiny person, dressed in a red Russian blouse.”2 The newspaper noted she entered the courtroom that day smiling and carrying flowers. Clearly, Steimer knew her way around a courtroom. She was sentenced to fifteen years in federal prison but was out on bail while she appealed the conviction. She made the most of her time. That spring Steimer returned to court when she was charged with seeking to overthrow the government.3 She was in federal court once again in September 1919, this time just a month before her refusal to stand as Weeks entered the courtroom, after dropping leaflets calling for “general strikes everywhere” and the “overthrowing of present society” from another New York building.4

Steimer was not on trial when she refused to stand for Weeks. She was in court that day to support friends. Still, she couldn’t help making a point using silent protest. Weeks did not appreciate her point. The jurist had the four-foot nine-inch Steimer brought to the front of the courtroom, where she refused to respond to his questions. After learning her name from others in the room, he told her, “I am informed that you are one of the most pronounced abhorrers of this Government.”5 Steimer’s reputation preceded her. Weeks let Steimer remain in the courtroom, reasoning a contempt charge would only make her a martyr. Her actions still grabbed headlines. The New York Times focused its trial coverage the next day on her behavior, headlining its story: “Girl Creates Stir at Anarchist Trial,” and dismissively noting “the young Russian girl” enlivened the proceedings.6 The story also listed past arrests for disorderly conduct and for having “thrown circulars from a roof of a building in Canal Street denouncing the National Security League’s Constitution Day.”7 Steimer wasn’t finished irking Weeks, however. Steimer booked another courtroom visit when she mailed Weeks an anarchist pamphlet titled “Arm Yourself” just days after she left his courtroom. Her helpful mailing to the jurist led to another arrest and more federal charges.8

Steimer seemed intent on testing as many of the boundaries of freedom of expression as possible in 1918 and 1919, particularly regarding the ideas the government would tolerate and the types of protections the First Amendment provided communicators. She wasn’t alone. While her case was unique in that it changed the face of how we understand free expression, Steimer’s protests came at a time of substantial change in US society. The headlines surrounding her various court visits tell the story of a quickly changing nation. World War I was transforming the industrial and diplomatic identities of the nation, as well as ushering in the Espionage Act, which represented a powerful, nationwide crackdown on unpopular expression. The temperance movement was fighting for prohibition. Massive waves of immigration in the 1880s and into the 1900s led overcrowded cities to swell with inequality and poverty.9 Workers, including immigrants, began to protest and organize for labor. Thousands rallied in Haymarket Square in Chicago in 1887, for example. One person was killed and many injured when police scuffled with protestors. Ultimately, four protestors were convicted and sentenced to death after a bomb was thrown near the police. The Haymarket Riot inspired more workers’ protests in major US cities.10

As workers started to fight for better wages and working conditions, women continued to fight for the right to vote. Alice Paul and the National Woman’s Party began picketing in front of the White House in 1917, making front-page news in November after police arrested forty-one protestors.11 While in government custody, Paul started her hunger strike, refusing to eat until being force-fed by guards. Women’s suffrage efforts failed in Congress multiple times in fall 1918, just as Steimer was facing charges for violating the Espionage Act. The Nineteenth Amendment was passed by Congress in June 1919. The nation was shifting. How we understood freedom of expression, something that had received little attention from the Supreme Court until this time, required explanation.12 Something had to change.

Steimer helped catalyze that change. Her protests and challenges to the ideas the government would tolerate led to a shift in how we understand free expression. These changes were of little help to her. The Supreme Court upheld her fifteen-year prison sentence for violating the Espionage Act, along with the sentences of three of her friends, in November 1919, about a month after her standoff with Weeks.13 New York media documented Steimer’s departure for a federal prison in Jefferson City, Missouri, noting she smiled and laughed, telling her mother and sister to cheer up.14 After brief stays in prison, Steimer and three of her coconspirators were deported to Russia. In the absence of a clear set of free-expression safeguards, particularly in a quickly changing nation, the United States simply shipped its free-expression problems elsewhere.15 While Steimer’s time in the United States was over—she continued to fight for her beliefs in Europe before living her final years in Mexico City—her influence on free expression, if not her name, has endured.

Steimer is seldom mentioned in First Amendment textbooks, though newspapers often referred to her as a socialist or anarchist leader.16 Her absence is largely because her case, Abrams v. United States, is named after her co-conspirator Jacob Abrams, whose story has become synonymous with one of the Supreme Court’s earliest efforts to define the First Amendment’s meaning.17 The case represents a landmark moment in free-expression history, marking the first time a justice wrote in support of the First Amendment. How the justice wrote about free expression, as well as who the justice was, changed the path of how the First Amendment is understood. While Steimer and Abrams were eventually reunited in Mexico City, decades after being expelled from the United States for expressing unpopular ideas, their case introduced the crucial but complex idea that freedom of expression requires space. This is a book about that space.

We often think of freedom of expression in terms of personal rights. People speak of “my rights” or “their rights,” but all expression must take place somewhere, whether it’s in Weeks’ courtroom, on Steimer’s and Abrams’s anti-government leaflets, on social media, or in the metaverse. The discussion about that somewhere started during a time of profound change in US society. Steimer’s and Abrams’s case marked a turning point in the discussion. In dissenting in their case, Justice Oliver Wendell Holmes introduced the concept of a space devoted to freedom of expression into the Court’s discussions. He did not suggest a specific physical location. Instead, he suggested a conceptual space. He made it sound simple, beginning with facetious reasoning. He explained:

Persecution for the expression of opinions seems to me perfectly logical. If you have no doubt of your premises or your power and want a certain result with all your heart you naturally express your wishes in law and sweep away all opposition.18

Holmes, in other words, reasoned limiting the flow of unpopular ideas only works if the government is certain of the truth.

Fundamentally, Holmes, a Civil War hero and a well-known legal mind, didn’t believe anyone could really know the truth.19 He blamed rigid, unmoving beliefs between North and South for causing a war that lead to the deaths of many of his friends.20 The war might have been over for more than fifty years before Steimer and Abrams distributed their fliers, but he never forgot, keeping bullets that were pulled from his body and his bloodied uniforms for the rest of his life.21 He reasoned, if no one can know absolute truth, society should be tolerant of a variety of ideas. He referred to the space in which ideas can be freely exchanged as a marketplace of ideas, explaining, “The best test of truth is the power of the thought to get itself accepted in the competition of the market.”22 He concluded, “That at any rate is the theory of our Constitution.”23

His dissent didn’t come at any ordinary time. The nation was struggling with all manner of protest and the Espionage Act, the first federal law to limit freedom of expression since the Alien and Sedition Acts of 1798. This wasn’t just any stuffy political appointee to the Supreme Court lamenting free expression either. This was the same Holmes the nation had read about in “My Hunt After the Captain,” his famous father’s riveting tale of his desperate search for his injured son after the bloody battle of Antietam that was published in The Atlantic in 1862.24 Importantly, the author who communicated these first ideas about the meaning of the First Amendment and a space for discourse was a well-respected legal mind. Holmes’s words about a space for free expression led to supportive and celebratory letters.25 His concern for a space for the exchange of ideas, in other words, made an impact, even if his ideas were part of a dissent.

Let’s be clear, however, Holmes didn’t invent the marketplace of ideas, and he absolutely did not complete it. His ideas were on the losing side of the case. A majority of the Court found limiting Steimer’s unpopular ideas did not violate the First Amendment. This moment, in other words, did not resolve much regarding freedom of expression, but the nationally known legal thinker’s concern for a space for discourse and his use of the marketplace concept ignited an important discussion about the exchange of ideas that has continued through more than a century of technological and social change. Alongside the marketplace concept, Holmes added truth and human rationality as foundational building blocks for why we should have freedom for expression. These difficult concepts remain central to how the space for the exchange of ideas is understood.

The marketplace ultimately, through decades of debate regarding its meaning, became the Supreme Court’s dominant rationale for why we have freedom of expression. It also became justices’ name for the space for the exchange of ideas in democratic society. Justices essentially attached freedom of expression to a particular map—the marketplace of ideas—which became the guide for what the space for the exchange of ideas looked like. While problems in the marketplace’s assumptions about truth and human rationality, which are discussed later in the book, make it a flawed tool for mapping a crucial place, its role in creating a protected conceptual space for discussion is crucial.

What is a conceptual space? This book often refers to the conceptual place as a space for discourse, rather than the marketplace of ideas. These words are chosen carefully. The space for discourse is a conceptual place because it doesn’t exist in a particular physical location. It is an imagined space that is meant to encapsulate and rationalize protecting freedom of expression. The space is, in other words, made up. It was created in jurists’ and scholars’ minds, ultimately entering the First Amendment’s precedential history in Steimer’s and Abrams’s case in 1919 when Holmes introduced it as the marketplace of ideas. This book assumes democracy requires a space for discourse but does not assume the space must be called the marketplace of ideas or retain the traditional assumptions that characterize the metaphor. One of the crucial points of this book is that the shape and boundaries of the conceptual space have always remained up for debate. Technological and social changes, particularly the emergence of networked technologies and artificial intelligence (AI), have created new urgency to concerns that the marketplace of ideas, as it has been built, is not up to the task of acting as the primary tool for how we understand the space for discourse. We need a new way of thinking about the space for discourse.

The space requires clear understandings regarding its makeup and a new foundation in the twenty-first century. Much as was the case during Steimer’s busy 1918 and 1919, the nature of the space has again changed, and the map no longer reflects the place it was created to describe. The space must be reimagined in light of these massive changes in how people make sense of the world around them, the AI entities that play persistent roles in molding our realities, and because its assumptions were never static or steady to begin with.

This book is divided into two parts in its examination of the future of the space for discourse. Part I encompasses the first five chapters and explores the nature of the space and the theoretical history and development of the marketplace concept. These chapters do not retell the same story about a static marketplace that was influenced by Enlightenment thinker John Milton and brought into the law by Holmes. Instead, these chapters tell the story of a living, dynamic idea that came to be a problematic and flawed Enlightenment-funded rationale for a space for human discourse. Chapters 1 and 2 do important work in providing a historically and theoretically grounded reframing of the traditional free-expression and marketplace-of-ideas narratives.

The chapters emphasize the space for discourse is an imagined place characterized by change, rather than stability. The marketplace of ideas, though justices generally present it as something that has always meant one thing, has been conceptualized in countless ways by many justices and scholars. These perspectives contribute a much more diverse set of understandings about how we should conceptualize the space for discourse in the networked, AI era. Chapter 3 continues to reframe and retrace the space’s history, digging deeply into Holmes’s philosophies regarding truth and human rationality. Both concepts, like Holmes himself, are fundamental to the US free-expression story. Chapters 4 and 5 trace the marketplace of idea’s eventual ascendancy as the Supreme Court’s primary tool for rationalizing and explaining freedom of expression. The chapters emphasize the uneven and highly contested development of the theory from a passing mention in Holmes’s dissent in Abrams to its use as a seemingly static, absolute rationale for nearly unrestricted freedom of expression in more recent First Amendment precedents.

Part II shifts the focus from looking back to looking ahead. Chapter 6 examines the impact networked technologies and AI are having on the flow of ideas and the shapes and contours of the space for discourse. The four chapters that follow draw together a collection of diverse theoretical lenses through which to reconsider the conceptual space in the networked era. These chapters draw from jurists, philosophers, and the European Union’s (EU’s) fundamentally different approach to constructing a conceptual space for human discourse. Using building blocks from these interdisciplinary perspectives, as well as the frameworks of the space that were identified in Part I, the book concludes by identifying fundamental, theory-level changes involving the nature of the space and how we conceptualize it, changing the truth assumptions that are inherent in the way we understand and rationalize expression in the space, and describing and envisioning the space based on principles and ideas rather than comparisons to physical places. Ultimately, these revisions help preserve a space for democratic discourse by restructuring the foundations in ways that support free expression in the networked, AI eras.


1. Abrams v. United States, 250 U.S. 616 (1919).

2. Heywood Broun, “Act Three—The Courtroom,” New York Tribune, Oct. 27, 1918, 21.

3. Hold Four, Charged with Advocating Overthrow of American Government,” Buffalo Enquirer, March 12, 1919, 3.

4. “Russian Girl Held for Showering Pamphlets from Rooftop,” New York Daily News, Sept. 19, 1919, 2.

5. “Girl Creates Stir at Anarchist Trial,” New York Times, Oct. 11, 1919, Page 24.

6. “Girl Creates Stir.”

7. Ibid.

8. “Molly Steimer, Red Agitator, Is Arrested,” New York Tribune, Oct. 19, 1919, 1.

9. See Jacob Riis, How the Other Half Lives (Cambridge, MA: Harvard University Press, 2010); Andrew Cornell, Unruly Equality (Berkeley, CA: University of California Press), 21–26, regarding immigration, poverty, labor strife, and anarchism during this period.

10. “Haymarket Affair,” Britannica, last updated June 9, 2023,

11. “Arrest 41 Pickets for Suffrage at the White House,” New York Times, November 11, 1917, 1.

12. See David M. Rabbin, Free Speech in its Forgotten Years (Cambridge, UK: Cambridge University Press, 1997), 2–8, for discussion regarding the catalyzing nature of the Espionage Act in inducing the Supreme Court to make its first decisions about the First Amendment’s meaning.

13. One of the original six conspirators was acquitted. Another died in jail while awaiting trial.

14. “‘Cheer Up!’ Girl Red Tells Weeping Mother at Parting in the Tombs,” New York Tribune, May 2, 1920, 1.

15. Steimer and Abrams weren’t the first critics the government deported. Emma Goldman, who was influential to Abrams and Steimer, was deported, along with 248 other dissidents, in December 1919. See “Burford Reaches Hango and Deported Radicals Go on to Russia by Train,” New York Times, Jan. 18, 1920, 1.

16. See “Girl ‘Red’ Leader ‘Totally Indifferent’ At Her Arraignment,” New York Tribune, Sept. 19, 1919, 20; “Goldman’s Power Gone,” St. Joseph News-Press, Dec. 17, 1919, 2, for examples.

17. See Abrams, 250 U.S. at 617–619 regarding Abrams’ presence in the case. Abrams is the only one of the four who were convicted who is mentioned in the Supreme Court case. See also Robert Post, “Reconciling Theory and Doctrine in First Amendment Jurisprudence,” California Law Review 88 (200): 2358–2360; Edward S. Corwin, “Freedom of Speech and Press Under the First Amendment Resume,” Yale Law Journal 30, no. 1 (1920): 50–55, for examples of the impact Holmes’ dissent in the Abrams decision had on free expression.

18. Abrams, 250 U.S. at 616 and 630 (Holmes, J., dissenting).

19. See chapter 3 for a full discussion of how Holmes understood truth.

20. Ibid.

21. Ibid.

22. Abrams, 250 U.S. at 630 (Holmes, J., dissenting).

23. Ibid.

24. Oliver Wendell Holmes, Sr., “My Hunt After the Captain,” The Atlantic, December 1862.

25. See Letter from Felix Frankfurter to Oliver W. Holmes (Nov. 26, 1919) (on file with Harvard Law School Digital Suite), for an example. See also chapter 3.