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Democracy, Hypocrisy, and the Urgency of the First Amendment

By: Alex Spiro

A noted Harvard-educated lawyer gives an impassioned plea for the primacy of the First Amendment—which might be the most consequential issue of our lifetime.

How can social media, technology, politics, and free speech coexist in a functioning democracy? It’s a question that has been brought before the Supreme Court, and an issue that will certainly play a factor in our presidential election and every election thereafter. The First Amendment also has relevance to our criminal justice system, our college campus culture, even our zoning laws. It has implications for everything from how legal disputes are resolved to why certain blocks have tons of porn shops. And at the center of this most defining issue of our time is lawyer Alex Spiro.

While Republicans think he’s a Democrat and Democrats think he’s a Republican, Spiro is, at his core, an unwavering believer in free speech. In this book, he takes readers through some of the most defining free speech cases of his career—from an NBA star’s clash with police, to the infamous “pedo guy” tweet Elon sent about a British caver, to mediating between financier Bill Ackerman and Harvard in the anti-Semitism uproar that followed the events of October 7, 2023 in Israel. Spiro also examines free speech in relation to other consequential events, such as the January 6, 2021, storming of the US Capitol. And he looks back at the history of the First Amendment, analyzing the Alien Enemies Act of 1798, which was invoked by President Donald Trump in 2025. He mixes engaging storytelling with constitutional law and history, urging readers to prod their own double-standards on the subject.