The Supreme Court’s Biggest Mistakes with C. Evan Stewart

Apr 28, 2026

We’re taught to believe the Supreme Court is the final word on justice—but history tells a more complicated story. In this episode of Free Thinking with Montel, Montel sits down with legal expert and author C. Evan Stewart to examine some of the most consequential—and controversial—decisions ever handed down by the U.S. Supreme Court. From Dred Scott v. Sandford to Plessy v. Ferguson to Korematsu v. United States, this conversation explores how the Court has, at times, upheld injustice, reinforced inequality, and allowed fear or politics to shape the law. But this isn’t just about the past. It’s about what these decisions reveal about the present—and the future. How does a system built on justice get it so wrong? And how do we recognize those moments in real time? This episode challenges the idea of legal infallibility and reminds us that the Court, like any institution, is shaped by the people—and the pressures—behind it. Because understanding history isn’t just about looking back. It’s about making better decisions moving forward.