Windy City Wisdom, a Chicago Style Media Production
What does “free speech” really mean in 2026—and where are the limits most people don’t understand?
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In this episode, we sit down with Barry McDonald, a constitutional law professor who has spent decades studying how the First Amendment actually works in real life—not just in theory. Barry has clerked for the Chief Justice of the United States Supreme Court, advised governments and technology companies, and regularly explains major legal issues for outlets like The New York Times, CNN, NPR, and Fox News. In this conversation, he cuts through the noise to explain what the Constitution truly protects, how free speech applies to private companies and social media, and why so much public debate around the First Amendment misses the mark. In this episode, we cover: • What the First Amendment actually protects • Free speech vs private platforms • Social media and constitutional limits • Why free speech is widely misunderstood Windy City Wisdom is a long-form conversation series exploring ideas, leadership, business, and culture through thoughtful, no-nonsense conversations. www.chicagostylemedia.com [https://www.chicagostylemedia.com/] 🎧 Subscribe for weekly episodes. 📲 Follow the show for clips and updates. This episode is for informational purposes only and does not constitute legal advice.
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