Michael: Most people think the Supreme Court is about nine brilliant legal minds debating dusty old texts. The truth is far more dramatic. It's a story of personal vendettas, political power plays, and one justice's outburst that decided a presidential election. It’s less a library, more a season of Succession. Kevin: Wow, Succession? That's a bold comparison. You're saying the highest court in the land is basically a family of billionaires fighting over who gets the company? I'm not sure if I should be entertained or terrified. Michael: A little of both, probably. And that's exactly the world that Jeffrey Toobin pulls back the curtain on in his book, The Nine: Inside the Secret World of the Supreme Court. It’s this incredible look at the human drama behind the robes. Kevin: I’ve heard of this book. It was a huge deal when it came out, right? Highly rated, but also pretty controversial depending on who you ask. What makes Toobin the guy to tell this story? Michael: He was perfectly positioned. As a long-time legal analyst for major news outlets and a staff writer for The New Yorker, not to mention a Harvard Law grad and former prosecutor, he had the access. He interviewed justices and more than seventy-five of their law clerks. So this isn't just gossip; it's deeply reported. He's showing us that the Court's decisions don't happen in a vacuum. They're forged in a crucible of ideology and personality. Kevin: Okay, so we're getting the real story, not the polished press release version. Where does this high-stakes drama even begin? Michael: It's fascinating. The modern battle for the Supreme Court didn't start with a landmark case or a presidential appointment. It started in a classroom at Yale Law School, with a student who just felt like he didn't fit in.

Kevin: Hold on, you’re telling me this massive political shift began with some awkward college kid? That sounds less like a political thriller and more like a coming-of-age movie. Michael: Exactly! But that's the origin story. It’s 1980, Ronald Reagan has just been elected, and a first-year law student at Yale named Steven Calabresi is in his torts class. The day after the election, his liberal professor is so distraught that he cancels the lesson to talk about the results. He asks for a show of hands: who voted for Jimmy Carter? Nearly every hand goes up. Then he asks who voted for Reagan. Only two hands go up, one of them being Calabresi's. Kevin: Oh, I know that feeling. The slow, sinking realization that you are completely alone in a room. That's brutal. Michael: It was a defining moment. Calabresi and other young conservatives at elite law schools like Yale and the University of Chicago felt like they were in enemy territory. The legal world was dominated by the legacy of the liberal Warren Court—the court of Brown v. Board of Education and expanded civil rights. They felt there was no intellectual home for their ideas. Kevin: So what did they do? Start a secret club in a basement somewhere? Michael: Pretty much! Calabresi, along with a few others, decided to create that home for themselves. They founded the Federalist Society. The idea was to build a network for conservative and libertarian law students and lawyers to debate ideas, challenge the liberal orthodoxy, and, most importantly, groom future leaders. Kevin: The Federalist Society. I've heard that name. They're a huge deal in conservative politics now. But at the time, was it just a debate club, or was there a bigger power play in mind from the start? Michael: That’s the million-dollar question. Initially, it was a space for ideas. They championed a philosophy called "originalism," which was popularized by figures like Robert Bork and Antonin Scalia. The core idea is that judges should interpret the Constitution based on the original intent of the framers in the 18th century. Kevin: What does that actually mean in practice? It sounds like trying to figure out what James Madison would think about the internet. Michael: It's a way to put a brake on what they saw as judicial activism. For liberals, the Constitution is a "living document" that adapts to modern times. For originalists, that's just a cover for judges making up law they like. Their prime example and ultimate target was Roe v. Wade, the case that legalized abortion. They argued that since the framers never mentioned a right to abortion, the Court had no business inventing one. Kevin: So this wasn't just a philosophical debate. It was a war, and Roe v. Wade was the key territory they wanted to reclaim. Michael: Precisely. And this is where the Federalist Society evolved from a student club into a political machine. It became a pipeline, a farm system for conservative legal talent. The Reagan administration, and later the Bush administrations, looked to the Federalist Society for recommendations for judicial appointments. They wanted judges who were committed to this originalist philosophy. Kevin: And this is where someone like Samuel Alito comes in? Michael: A perfect example. Toobin uncovers this memo Alito wrote in 1985 when he was a young lawyer in the Reagan Justice Department. He was applying for a promotion and wanted to show off his conservative credentials. In the memo, he proudly states he went to law school specifically to challenge the legacy of the Warren Court. And he lays out a strategy for the government to attack Roe v. Wade. Kevin: A strategy? What was it? Michael: It was brilliant and patient. He argued that the government shouldn't try to overturn Roe in one fell swoop. That would be too dramatic and might fail. Instead, he advocated for a strategy of chipping away at it, supporting state laws that added more and more restrictions on abortion. The goal was to create a series of cases that would gradually erode the foundation of Roe until it eventually collapsed. Kevin: Wow. So he was playing the long game, even back then. That's not just a legal argument; that's a multi-decade political campaign plan. It’s incredible to see how a small group’s ideological frustration could build into such a powerful, systematic force that would go on to reshape the entire judiciary. Michael: It's a testament to organization and long-term vision. They built an intellectual and political infrastructure that liberals simply didn't have on their side. And that infrastructure set the stage for some of the most intense, high-stakes drama the Court has ever seen. Because when these justices, products of this new political reality, were faced with a national crisis, it wasn't just about the law. It was deeply personal.

Kevin: Okay, so you have this ideological battlefield set up. You have these two armies, the living constitutionalists and the originalists, who have been fighting for decades. What happens when a bomb goes off in the middle of it? Michael: That bomb was the 2000 presidential election. And Toobin's reporting on Bush v. Gore is just jaw-dropping. It completely shatters the myth of the Court as a serene, impartial institution. Kevin: This is the part of the book that gets a lot of attention, and where some critics say Toobin’s own liberal leanings show. What's the story he tells? Michael: He takes us right inside the Court as the chaos unfolds in Florida. The key figure in all of this is Justice Sandra Day O'Connor. She was the quintessential swing vote, the pragmatic centrist who often decided the Court's most important cases. She was a Republican, appointed by Reagan, but she was a moderate, not an ideologue. Kevin: She was seen as the most powerful woman in America for a while, right? Because her vote was always the one that mattered. Michael: Absolutely. And on election night 2000, she's at a party in Washington D.C. The early results are coming in, and for a moment, it looks like Al Gore is going to win Florida and the presidency. According to Toobin's sources, when O'Connor hears this, she lets out an audible gasp and says, "This is terrible!" Kevin: Wait. A sitting Supreme Court justice reacted to an election result—before any case had even been filed—with a purely personal, political opinion? That's… not great. Michael: It's a stunning moment. Her husband had to calm her down, saying the results weren't final. But it reveals so much. It shows that before she was a judge ruling on the law, she was a citizen—and a Republican—with a strong preference for the outcome. That personal feeling, Toobin argues, colored everything that came after. Kevin: So when the case, Bush v. Gore, finally reached the Supreme Court, what was the atmosphere like inside the building? Michael: Tense. Divided. The five conservative justices—Rehnquist, Scalia, Kennedy, Thomas, and O'Connor—were furious with the Florida Supreme Court. They felt the Florida judges, who were mostly Democrats, were changing the rules to try and hand the election to Gore. The four liberal justices—Stevens, Souter, Ginsburg, and Breyer—were horrified that the U.S. Supreme Court would even consider getting involved in a state election dispute. Kevin: It sounds less like a legal deliberation and more like a political gang war. Michael: That's a good way to put it. Toobin describes Justice Scalia as being so angry he wanted to stop the Florida recount immediately, without even hearing oral arguments. He was convinced it was an illegitimate process. On the other side, you had justices like David Souter who were deeply committed to the idea of judicial restraint and believed the Court was about to do something catastrophic to its own reputation. Kevin: And O'Connor is the one in the middle, holding all the cards. Michael: She is. And her frustration and impatience with the whole messy process seemed to drive her decision. She felt the voters had their chance and that it wasn't the Court's job to decipher ambiguously marked ballots. Ultimately, she sided with the conservatives in a 5-4 decision to stop the recount, effectively making George W. Bush the next president. Kevin: That is just mind-blowing. The fate of the presidency coming down to a 5-4 vote, driven as much by personal frustration and political alignment as by legal principle. What was the fallout inside the Court? Could they just go back to being colleagues after that? Michael: Not really. The wound was deep. Toobin reports that Justice Souter was so devastated by the decision, so convinced that the Court had acted as a partisan political body, that he seriously considered resigning. He felt the institution he had dedicated his life to had betrayed its principles. Kevin: He considered quitting? Wow. Michael: He ultimately stayed, but his colleagues said he was never the same. He became more withdrawn, more cynical. It shows that these aren't just abstract legal disputes for them. They have real, emotional consequences. Toobin tells another story that perfectly captures this human side of the court, even in a less world-altering context. Kevin: What's that? Michael: A massive snowstorm hits Washington D.C. The city is completely shut down. But Chief Justice Rehnquist, a stickler for tradition and order, insists that the Court will hear arguments as scheduled. So the justices have to find a way to get to work. Kevin: I love this. It's like a sitcom episode. Michael: It really is. Justice Scalia has to walk a half-mile through waist-deep snow to get to a jeep the Court sent for him. He's furious the whole way. Justice Ginsburg, ever elegant, shows up in a straight skirt and high heels and has to be physically carried to the car by the driver. And Justice Souter, the rugged individualist from New Hampshire, tries to drive himself, gets his car stuck in a snowbank, and has to be rescued by the Supreme Court police. Kevin: That's incredible. It tells you everything you need to know about their personalities right there. Scalia is fuming, Ginsburg is impractical, and Souter is trying to do it all himself. It humanizes them in a way that reading a legal opinion never could. Michael: Exactly. And that's the core insight of The Nine. These are not disembodied legal brains. They are nine complex, flawed, and fascinating human beings. And their personalities, their relationships, their anger, their friendships—all of it gets baked into the laws that shape our country.

Kevin: So when you put it all together, what’s the big picture Toobin is painting? On one hand, you have this highly organized, ideological movement, the Federalist Society, working for decades to install a certain type of judge. On the other hand, you have the chaotic, unpredictable reality of human nature. Michael: That's the central tension of the book. The conservative legal movement successfully created the players and set the ideological battlefield. They got their people onto the Court. But they couldn't control the outcome of the game, because you can't script human interaction. You can't predict how someone's personal frustration, like O'Connor's, will intersect with a national crisis. Kevin: So the "secret world" of the Supreme Court isn't some grand conspiracy. It's just... people. Michael: It's the unpredictable collision of grand ideology and messy human personality. The law is supposed to be about principles that are impartial and enduring. But Toobin shows us that those principles are filtered through nine very different, very human individuals. Their personal histories, their private beliefs, their relationships with each other—that's the secret ingredient that ultimately determines the law of the land. Kevin: It's a bit unsettling, honestly. It makes the whole system feel so much more fragile. But it also makes it more understandable. It’s not some unknowable, mystical process. Michael: Right. It demystifies it. And I think that's the book's greatest contribution. It forces us to see the Court not as we wish it were, but as it is: a profoundly human institution, with all the brilliance, bias, and drama that entails. Kevin: It leaves me with a big question, though. Can we ever truly separate the law from the people who interpret it? And if we can't, what does that mean for our trust in the entire system? Michael: That's the question that hangs over the entire book, and it's more relevant today than ever. Does knowing this human side of the Court make you more or less confident in its decisions? It's something worth thinking about. We'd love to hear what you think. Michael: This is Aibrary, signing off.