So to Speak: The Free Speech Podcast
Episode 264: Anonymity from the Founding to the Digital Age
Host: Nico Perrino (FIRE)
Guest: Jeff Kosseff, Senior Legal Fellow, Future of Free Speech, Author of The United States of Anonymous
Date: February 25, 2026

Episode Overview

This episode explores the tradition, importance, controversy, and legal evolution of anonymous speech in America, tracing its origins from the Revolutionary era to today's digital age. Host Nico Perrino interviews Jeff Kosseff, a legal scholar and author, to uncover why anonymity was essential for the Founders, how its protection has been challenged and interpreted by the courts, and the implications for free expression in a world of growing calls for online accountability, age verification, and identity requirements.

Key Discussion Points & Insights

1. Defining Anonymity vs. Pseudonymity

• Anonymity: Complete separation of identity from speech or action ([02:03]).
• Pseudonymity: Use of a persistent alias or pen name, not tied to legal identity ([02:14], [02:28]).

“Anonymity is the ability to separate your identity from your speech or other activities that you're associated with.” —Jeff Kosseff [02:03]

• Motivations for Anonymity:
  • Legal concerns (fear of lawsuits/arrest)
  • Safety (protection from threats/retaliation)
  • Economic fears (loss of livelihood)
  • Privacy (sharing controversial or personal thoughts)
  • "Speech motivation" (ideas stand on their merit, unclouded by author’s identity or history) ([02:35]–[04:37])

"Your speech is simply different than when you're saying it under your real name... by associating their real identity with these thoughts and this expression, they might be undercutting the actual value of the ideas by having that baggage associated with it." —Jeff Kosseff [04:02]

2. Anonymous Speech in Early America

• Revolutionary Tradition: Over half of political pamphlets between 1763–1765 were published anonymously ([07:39]).

• Motivations:

  • Fear of retaliation from British authorities (e.g., seditious libel punishments)
  • Desire to focus debate on arguments, not personalities

• Key Examples:

  • John Peter Zenger (1735): Publisher tried for seditious libel for criticizing colonial governor; published controversial anonymous speech ([05:44]).
  • Common Sense (1776): Thomas Paine signed as “an Englishman”; valued idea over identity ([08:06]; see quote below).
  • Federalist Papers (1787–88): Hamilton, Madison, Jay wrote as “Publius” to focus on ideas and avoid personal bias ([08:06]–[11:26]).

“Writing who the author of this publication is is wholly unnecessary to the public, as the object for attention is the doctrine itself, not the man.” —Thomas Paine, quoted by Nico Perrino [11:26]

• Junius: Influential anonymous troll in 1760s London; evaded identification while harshly criticizing powerful figures ([12:23]–[15:03]).

“If I were known, I could no longer be a useful servant to the public. The mystery of Junius increases his importance.” —Junius, quoted by Nico Perrino [15:03]

3. Was Anonymity Intended as a Protected Right?

• Constitutional Debate:
  • Justice Thomas: Anonymity was integral to founding-era free speech and press ([16:15]).
  • Justice Scalia: Anonymity is separate from protected speech and press rights; freedom lies in publishing, not in withholding identity.
• Originalist Dispute:
  • 1995 Supreme Court opinions clashed over whether anonymity was implicit in the First Amendment ([16:15]–[18:18]).

“If you would ask Justice Thomas, he would say that freedom of press and of speech includes the right to be anonymous... If you asked late Justice Scalia... he would say, absolutely not.” —Jeff Kosseff [16:15]

4. Legal Evolution: From Anonymous Association to Online Speech

• NAACP v. Alabama (1958): First major case linking anonymity to First Amendment rights, focusing on association; Alabama tried to compel NAACP membership disclosure to suppress desegregation advocacy; Supreme Court protected anonymous association ([20:53]–[23:51]).
• Early Ku Klux Klan Masking Laws:
  • Supreme Court previously permitted forced disclosure of Klan officers (1928); later decisions and mask laws have been inconsistently applied ([24:10]–[27:14]).
  • Modern anti-mask laws often target political rallies but can chill anonymous assembly and protest ([27:14]–[29:44]).

“It's a very persuasive brief… if their First Amendment rights are threatened, our First Amendment rights can be threatened as well.” —Jeff Kosseff on Al Sharpton’s National Action Network supporting Klan’s mask rights [26:46]

5. Anonymity and the Digital Age

• Renaissance of Anonymity in the 1990s:
  • Pamphlet cases extend right to anonymous speech ([31:16]).
  • Online Test Case: Yahoo Finance message boards and the rise of John Doe lawsuits; companies routinely unmasked and retaliated against anonymous critics until courts intervened ([32:10]–[35:42]).

“The executives had never experienced anything like this before... now suddenly, they had their own employees having the nerve to go online and write negative things about their decision making. And this infuriated them, to put it mildly.” —Jeff Kosseff [32:58]

• Judicial Standards Developed: Civil courts now require strong cases with adequate showings to permit unmasking (varies by state) ([35:42]).

• Administrative Subpoenas:

  • Federal agencies like DHS can attempt to unmask users through administrative (non-judicial) subpoenas, raising serious procedural and notice concerns ([35:42]–[37:31]).
  • Key Question: Does the target of the subpoena get notified and have a chance to challenge?

6. Current and Looming Challenges: Age and Identity Verification

• Laws Requiring Age Verification:

  • Laws in Texas (Free Speech Coalition v. Paxton) and elsewhere seek to block minors from social media/pornography ([38:14]–[40:03]).
  • Critics note that verifying minors’ ages would require everyone to submit identification, destroying anonymous use for adults, too ([38:14]–[41:42]).

• Anonymity as an Afterthought:

  • Courts striking down age-verification laws have often neglected the anonymity argument as central ([40:03]).
  • Data breaches and privacy concerns with verification systems are real and recurring ([41:07]).

• Anonymity Is Not Binary:

  • Platforms and technologies offer varying levels of anonymity based on policy; government-mandated identification is more concerning than private platform choices ([41:42]–[47:53]).

7. The Future: Erosion of Anonymity?

• Predictions:
  • Both guest and host express concern that public pressure for child safety and crime prevention may push the U.S. toward comprehensive identity verification online, threatening First Amendment anonymity ([47:53]–[48:47]).
  • Loss of internet "exceptionalism"—shift away from early ideals of cyberspace as a free frontier ([48:47]–[49:25]).

“I sadly see that as the future that we're headed towards. And I think that it's going to be hard to go back from that.” —Jeff Kosseff [48:47]

• John Perry Barlow’s Declaration of the Independence of Cyberspace: Cited to illustrate the lost utopian vision ([49:25]).

Notable Quotes & Memorable Moments

• “The arguments helped shape a nation, but the author's real identities and names were nowhere to be found.” —Nico Perrino, on the Founders’ use of pseudonyms [00:59]
• "Writing who the author of this publication is... the object for attention is the doctrine itself, not the man.” —Thomas Paine, as discussed [11:26]
• “If I were known, I could no longer be a useful servant to the public. The mystery of Junius increases his importance.” —Junius, quoted [15:03]
• "There is a right to be able to associate without having your name automatically disclosed. And it's not absolute, but you can't just pierce that anonymity for no reason at all, which is essentially what's happening here." —Jeff Kosseff, on NAACP v. Alabama [22:59]
• "You saw the Hong Kong protests... where a lot of the protesters wore masks because of the facial recognition tools..." —Nico Perrino, discussing modern parallels [27:53]
• “Anonymity isn’t binary... there’s a spectrum.” —Jeff Kosseff [41:42]
• "The Internet, for more than 30 years of... commercialized Internet, has been characterized by this openness and this exceptionalism. And I think that the erosion of anonymity is one of the products of just the broader shutdown of this Internet exceptionalism.” —Jeff Kosseff [48:47]
• “We are creating a world where anyone, anywhere, may express his or her beliefs, no matter how singular, without fear of being coerced into silence or conformity.” —John Perry Barlow, quoted by Nico Perrino [49:25]

Key Timestamps

• [02:03] – Definition of anonymity and pseudonymity
• [04:37] – Reasons/motivations for anonymity in speech
• [07:39] – Historical prevalence of anonymous pamphleteering
• [08:06] – Federalist Papers, Thomas Paine’s motivations
• [12:23] – “Junius” and the impact of anonymous criticism
• [16:15] – Debate among Supreme Court justices about constitutional protection of anonymity
• [20:53] – NAACP v. Alabama and the right to anonymous association
• [24:10] – Ku Klux Klan, anti-mask laws, and conflicting court rulings
• [31:16] – The legal turning point in the 1990s; online anonymity cases
• [32:10] – Yahoo Finance test case for online anonymous speech
• [35:42] – Courts developing standards for unmasking anonymous speakers
• [35:42]–[38:14] – Administrative vs. judicial subpoenas and their dangers
• [38:14] – Age verification laws and risks to anonymity
• [41:42] – Anonymity as a spectrum, not binary
• [47:53] – Future prospects: Will legal anonymity survive?
• [49:25] – Reflections on the lost utopian promise of the Internet

Final Thoughts

Summary:
American democracy was shaped by anonymous speech, defended for reasons of safety, privacy, and the integrity of ideas themselves. From the Founders’ pseudonyms to modern digital debates, its legal protection has been hard-fought, often ambiguous, and currently under threat. New laws targeting online anonymity, especially age verification requirements, present a fundamental challenge to this tradition, and courts’ contemporary decisions will likely determine whether anonymity remains a core feature of democratic free expression in America.

Guest’s Outlook:
Jeff Kosseff foresees a future of decreased online anonymity, as legislative and societal pressures drive increased identification. He urges vigilance and legal advocacy to defend this “essential” First Amendment value.

For Further Reading:

• Jeff Kosseff, The United States of Anonymous
• Upcoming: The Future of Free Speech with Jacob Mchangama (preorder link in show notes)

Series Note:
Part of FIRE’s series marking America’s 250th anniversary—exploring how expression created and challenged the nation.