
Comey: Mob Bosses & Presidents
13 minTruth, Lies and Leadership
Golden Hook & Introduction
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Jackson: What if the best way to understand the highest levels of American government... is to first understand the Mafia? Olivia: That sounds like a wild claim, Jackson. Jackson: It sounds crazy, right? But today we're exploring how a former FBI Director's early days prosecuting mobsters gave him a framework for dealing with presidents. It’s a journey from organized crime to the Oval Office, and the rules of the game are surprisingly similar. Olivia: That's the wild journey at the heart of A Higher Loyalty: Truth, Lies, and Leadership by James Comey. Jackson: Right, the former FBI Director. And this isn't just some political tell-all. Comey was a career prosecutor, a registered Republican for most of his life, who ended up serving under both President Bush and President Obama before his very public, very dramatic clash with President Trump. That unique path is what makes his perspective so fascinating. Olivia: Exactly. He's not just a political figure; he's someone who spent decades thinking about justice and leadership. And as you said, that journey starts in a very unexpected place: with the mob.
The Foundation: What is 'A Higher Loyalty'?
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Olivia: Comey starts his career as a young prosecutor in New York, and he becomes obsessed with taking down La Cosa Nostra, the American Mafia. He describes this world as "The Life," and it’s built on a very specific kind of loyalty. Jackson: The kind of loyalty we see in the movies, right? Omertà, the code of silence, loyalty to the boss above all else. Olivia: Precisely. But Comey pulls back the curtain on it, and what he finds is fascinating. He tells the story of Sammy "The Bull" Gravano, a high-ranking mobster who became a federal witness. Gravano described his own Mafia initiation ceremony. He’s brought into a room with the bosses, there’s a gun and a knife on the table, and they ask him a simple question: "Do you know why you're here?" Jackson: Wait, let me guess. The answer is obviously "yes, to be initiated into the mob," but you're not supposed to say that. Olivia: You got it. The correct answer is "no." Because "The Life," as Comey puts it, begins with a lie. You have to pretend you're clueless. The entire foundation of this world of so-called "honor" is built on deception. Gravano also talks about the Mafia's rules: you can't kill a "made man" without permission, you can't sleep with another member's wife, you can't deal drugs. Jackson: And I'm guessing those rules were... flexible. Olivia: Completely. They were broken all the time, especially by the bosses. The loyalty was a one-way street. It was demanded from below, but not reciprocated from above. The boss could lie to you, betray you, even have you killed, and it was all part of the game. For Comey, this becomes a powerful negative model. He sees this transactional, self-serving loyalty as the ultimate form of corruption. Jackson: Okay, so that's what loyalty isn't. It's not this blind, fearful obedience to a powerful person. So what is Comey's "higher loyalty"? What's the alternative? Olivia: It's loyalty to something outside of yourself and outside of any one person. It's loyalty to a set of lasting values—truth, integrity, and the rule of law. It’s loyalty to the institution, like the FBI or the Justice Department, and the principles it's supposed to represent. Jackson: That sounds noble, but isn't that a bit abstract? In the real world, don't you have to be loyal to people, to your team, to your boss? Olivia: It's a great question, and Comey argues that this abstract idea was forged for him not just in a courtroom, but in a moment of pure terror. When he was a teenager in 1977, a notorious serial attacker known as the "Ramsey Rapist" broke into his family's home. The gunman held Comey and his younger brother at gunpoint. Jackson: Oh wow. I had no idea. That’s terrifying. Olivia: He describes looking down the barrel of the gun, absolutely certain he was about to die. His brother managed to escape through a basement window and get help, and a neighbor with a large dog scared the attacker away. But that experience, that brush with death, changed him. He writes that it gave him a profound empathy for victims and a deep-seated desire to stand between the bully and the weak. It wasn't an abstract idea anymore; it was a visceral calling to serve justice. Jackson: So his "higher loyalty" isn't just a philosophical concept. It's rooted in this incredibly personal, traumatic event. He wants to be the person who protects people from the bad guys. Olivia: Exactly. It's a loyalty to the purpose of justice, not the personalities involved in it. And that strong moral compass is about to be tested in the most intense political storm imaginable.
The Crucible: Navigating the 'No-Win' Clinton Investigation
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Jackson: Okay, so he has this strong moral compass forged by mobsters and trauma. But how does that hold up under real political pressure? Let's talk about the 2016 election and the Hillary Clinton email investigation. This is where Comey becomes this hugely controversial figure. Olivia: It's the ultimate crucible for his philosophy. The investigation, which he code-named "Midyear Exam," was into whether Clinton mishandled classified information by using a private email server as Secretary of State. The FBI team concludes in July 2016 that while her actions were "extremely careless," there wasn't evidence to prove she had criminal intent, so they recommend no charges. Jackson: And that's where the story should have ended, but it didn't. Olivia: Not even close. The first problem arises when Attorney General Loretta Lynch has a private meeting with Bill Clinton on an airport tarmac in Phoenix. It creates a massive political firestorm and the appearance of a conflict of interest. To preserve the Justice Department's credibility, Lynch says she'll accept whatever recommendation the FBI makes. Jackson: So she basically throws the hot potato to Comey. He's now the sole public face of this decision. Olivia: He is. And he decides he has to be transparent to protect the FBI's reputation. He holds a press conference explaining in detail why they aren't recommending charges, laying out all the "extremely careless" behavior. This infuriates Democrats, who feel he's smearing their candidate, and Republicans, who think he's letting her off the hook. He's getting hit from both sides. Jackson: He's roadkill in the middle of the highway. But the real explosion comes later. Olivia: The real explosion comes on October 28, 2016, just 11 days before the presidential election. The FBI, during a separate investigation into disgraced congressman Anthony Weiner, discovers a laptop. And on that laptop are hundreds of thousands of emails from Huma Abedin, Weiner's wife and Clinton's top aide. Many of these emails appear to be from Clinton's private server, including potentially the ones that were missing from the start of her tenure. Jackson: Oh man. I remember the shockwave that sent. So what does Comey do? He's in an impossible position. Olivia: He describes it as a "speak or conceal" dilemma, and both options are terrible. Option one is to 'Conceal.' Say nothing. The FBI has the emails, but they can't possibly review them all before the election. If they stay quiet and Clinton wins, and then it leaks that the FBI sat on this information, the new president would be seen as illegitimate. The FBI's credibility would be, in his words, "catastrophic." Jackson: Okay, that's bad. What's the other option? Olivia: Option two is to 'Speak.' Tell Congress they've found new emails and are reopening the investigation. This would be transparent, but it would also be an unprecedented intrusion into a presidential election, and it could unfairly damage Clinton's campaign, especially if the emails turn out to be nothing new. Jackson: But Olivia, the backlash was immense. Many people, including a lot of analysts and pollsters, believe his choice to 'speak' cost Clinton the election. He effectively put his thumb on the scale. How does he justify that? Olivia: His logic, and he walks through it painfully in the book, is that he had to protect the institution of the FBI. He believed that concealing the information would do more long-term damage to the country's faith in the justice system than speaking would. He felt he had to choose the course of action that, while awful, would allow the FBI to maintain its "reservoir of trust" with the American people, no matter who won. He chose what he saw as the lesser of two evils to protect that higher loyalty to the institution. Jackson: Wow. So he's not thinking about the political outcome, he's thinking about the FBI's reputation in the years to come. It’s a decision that’s almost guaranteed to make everyone angry in the short term. Olivia: And it did. But for Comey, that was the price of leadership. He believed his duty was to the institution, not to a political candidate or party. And that unwavering, almost rigid, commitment to his idea of loyalty is about to lead to a direct collision with a new president who has a very, very different idea.
The Collision: A Mafia Boss in the White House?
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Olivia: So, after navigating that political minefield, Comey finds himself face-to-face with a new president, Donald Trump, who has a very different, almost... familiar, idea of loyalty. Jackson: Familiar how? You mean like the mob bosses he used to prosecute? Olivia: That's exactly the parallel Comey draws, and it's chilling. It starts just after the election. The heads of the intelligence community, including Comey, go to Trump Tower to brief the President-elect on Russian interference. After the main briefing, Comey is asked to stay behind to privately inform Trump about the existence of the now-infamous Steele Dossier, which contained salacious and unverified allegations. Jackson: That must have been the most awkward conversation in history. Olivia: Incredibly. Comey is terrified that Trump will see it as a threat, as the FBI holding something over his head. But the real test comes a few weeks later. Comey gets an unexpected call from the White House. The President wants to have dinner with him. Just the two of them. Jackson: A private dinner. That sounds... unusual. The FBI director is supposed to maintain independence. Olivia: It's highly unusual. Comey is very uncomfortable. They end up in the Green Room of the White House, at a small table set for two. After some small talk, Trump gets to the point. He looks at Comey and says, "I need loyalty. I expect loyalty." Jackson: Wow. That's... blatant. It's like the opening scene of a mob movie. He’s asking the head of the FBI to pledge fealty. How did Comey even respond to that? Olivia: He just stares at Trump. He describes this long, awkward silence. He knows he can't give that pledge. It would violate everything he believes in. So he tries to find a way out. He says, "You will always get honesty from me." But Trump isn't satisfied. He presses him again. Finally, Comey offers, "You will have honest loyalty." He tries to reframe it around his core values. Jackson: "Honest loyalty." That's a very careful choice of words. It's not the personal, blind loyalty Trump is asking for. Olivia: Exactly. It's loyalty to the truth, to the office, but not to the man. And this tension just keeps escalating. A few weeks later, in the Oval Office, Trump asks everyone else to leave the room, including the Attorney General, and then tells Comey, "I hope you can see your way clear to letting this go, to letting Flynn go." He's talking about the investigation into his former National Security Advisor, Michael Flynn. Jackson: That's a direct request to drop a criminal investigation. That's crossing a major line. Olivia: It's a shocking moment. Comey is stunned. He again gives a non-committal answer and immediately goes back to his car and writes a detailed memo about the conversation, because he knows how significant it is. He sees it as a direct assault on the rule of law. Jackson: And we all know how this story ends. Olivia: We do. The pressure continues, and on May 9, 2017, Comey is in Los Angeles for an FBI recruiting event. He's speaking to a group of employees when he sees his face flash on the TV screens behind him with the headline: "COMEY FIRED." He thought it was a prank. But it was real. He was fired, he believes, because he wouldn't pledge that personal, mob-style loyalty. He wouldn't stop the Russia investigation.
Synthesis & Takeaways
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Olivia: So in the end, the book isn't just a political memoir. It's a case study in what happens when two fundamentally different worlds collide: the world of institutional loyalty to abstract principles like 'truth,' and the world of personal, transactional loyalty to a powerful leader. Jackson: It's a story about a man who spent his life believing in a certain code, a higher loyalty, and then came face-to-face with a leader who operated by a completely different, and in Comey's view, much more dangerous one. The book is polarizing, and people can debate his decisions, but the central conflict is incredibly compelling. Olivia: He argues that this is the central challenge for any leader and, really, for any citizen. Are you loyal to a person, a tribe, a political party? Or are you loyal to a set of values that are supposed to endure beyond any single person's power? Jackson: It really makes you ask yourself, especially in your own life and career: what is your 'higher loyalty'? Is it to your boss, your team, your company... or something else entirely? It’s easy to say it’s about principles, but when you’re in the hot seat, like Comey was, that’s a much harder choice to make. Olivia: It's a tough question, and we'd love to hear what you think. Find us on our socials and let us know your take on Comey's choices and this idea of a higher loyalty. Jackson: We're always curious to hear how these ideas land with you all. Olivia: This is Aibrary, signing off.