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Mayor of Crazytown

12 min

A Washington Memoir

Golden Hook & Introduction

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Michael: Alright Kevin, you're a freshman congressman in 2013. A ten-inch knife is held to your throat by a colleague on the floor of the House. What's your next move? Kevin: Honestly? Probably what Boehner did. Swear at him and then, years later, become good friends. That's Washington in a nutshell, isn't it? A place where a death threat is just a spicy form of networking. Michael: It’s the perfect entry point into the wild world of John Boehner's memoir, On the House. This isn't your typical, polished political autobiography. This book was an instant #1 bestseller, and it's famous for its unfiltered, barstool-storytelling style. Kevin: I've heard the audiobook is legendary. Apparently, Boehner, who narrates it himself, went off-script to add a few extra choice words for his political enemies. Michael: He absolutely did. It’s less a memoir and more like eavesdropping on a guy at the end of the bar who has seen it all and is finally ready to talk. And his central topic, the one he keeps coming back to, is the nature of power. Kevin: That's what I'm curious about. We see the Speaker of the House on TV, banging the gavel, and assume they're the king of the castle. But Boehner paints a very, very different picture.

The Art of (Real) Power vs. The Illusion of Control

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Michael: Exactly. He argues that real power is often the opposite of what we think it is. It’s not about being the loudest person in the room. In fact, he quotes Margaret Thatcher: "Being powerful is like being a lady. If you have to tell people you are, you aren’t." Kevin: I like that. So who did he think embodied that kind of real, quiet power? I'm guessing it wasn't someone from his own party's "chaos caucus." Michael: Not even close. The person he holds up as the master of wielding power is his old political rival, Nancy Pelosi. He has this incredible story that perfectly illustrates her style. It’s about a congressman named John Dingell. Kevin: The name sounds familiar. A big deal? Michael: A legend. The "Dean of the House." He’d been in Congress since the Eisenhower administration. He was the powerful chairman of the House Energy and Commerce Committee, a position he held with an iron grip. But he was a moderate Democrat, and by the time Pelosi was Speaker, the party was moving left, especially on environmental issues. Kevin: And Dingell, coming from Michigan, was probably friendly with the auto industry. Michael: Precisely. So another, more liberal congressman, Henry Waxman, decides to challenge Dingell for the chairmanship. This was a huge deal in D.C. – it was like challenging a monument. And throughout the whole fight, Pelosi remained "officially neutral." Kevin: Ah, the classic "officially neutral" which means you're absolutely not neutral. Michael: You got it. Boehner says she never showed her hand, never left any fingerprints, but everyone knew she was tacitly backing Waxman. And when the secret ballot was counted, Waxman won by 15 votes. Dingell, the institution, was gutted. He was effectively stripped of his power overnight. Kevin: Wow. And Pelosi’s hands were clean, at least publicly. That’s a masterclass in political maneuvering. It’s brutal. Michael: It’s brutal, but it’s effective. Boehner’s point is that Pelosi understood that power isn’t about making speeches; it’s about controlling outcomes. He contrasts that with another story, this time about Mitch McConnell. Early in his leadership, Boehner had a meeting with McConnell and tried to show off how much he knew about the Senate’s inner workings. Kevin: A classic mistake. Never try to tell someone you know their job better than they do. Michael: McConnell let him finish, and as he was walking out the door, he just turned to Boehner and said something to the effect of, "You think you know the Senate. You will never know the Senate. I know the Senate." It was a quiet, devastating power move. It put Boehner right back in his box. Kevin: So real power is about quiet execution and deep institutional knowledge, not just being the one with the title. But that raises the question: what kind of power did Boehner himself have? If he admired Pelosi's ruthlessness but didn't seem to practice it, what was his style? Michael: His style was more relationship-based. He came from a family of 12 kids, worked in his dad's bar. He believed in talking to people, making deals, finding common ground. He wanted to be the friendly bartender of the House. Kevin: And how did that work out for him? Michael: It ran headfirst into a brick wall. A group of people who didn't want a friendly bartender. They wanted to burn the bar down.

The Mayor of Crazytown: Navigating Political Dysfunction

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Michael: This is the part of the book where Boehner becomes the self-proclaimed "Mayor of Crazytown." He's talking about the rise of the Tea Party and what he calls the "chaos caucus" within his own party. These were members, he says, who had no interest in governing. Their goal was to be on cable news. Their business model was outrage. Kevin: This is starting to sound very familiar. He’s describing a shift from policy to performance. Michael: Exactly. And the ultimate example of this was the 2013 government shutdown. The goal, pushed by Senator Ted Cruz and others, was to defund Obamacare. Boehner knew it was a suicide mission. They had no leverage. The Democrats controlled the Senate and the White House. There was a zero percent chance of it working. Kevin: But his own party forced his hand. Michael: Completely. He describes Cruz as a "reckless asshole who thinks he is smarter than everyone else." He says Cruz whipped up the base and the conservative media into a frenzy, making promises he knew he couldn't keep. Boehner felt he had a choice: either lead the charge off the cliff or be thrown off it. As he puts it, "A leader without followers is just a guy taking a walk." Kevin: So he went along with a strategy he knew would fail, just to maintain his leadership position. That's a tough look. Critics of the book point to this and say he's trying to have it both ways—blaming the crazies while admitting he enabled them. Michael: He doesn't really hide from that. He basically says he had to let them touch the hot stove to learn it was hot. The shutdown happened, it was a disaster for the Republican brand, and they got nothing. Boehner says it was a perfect example of "snatching defeat from the jaws of victory," because right as the shutdown started, the Obamacare website rollout was a technical catastrophe. If they had just let that play out, the political victory would have been handed to them. Instead, they made themselves the story. Kevin: It’s a fascinating insight into the psychology of these movements. The goal isn't to win; the goal is to fight. The performance of fighting is the victory. Michael: And to raise money off that performance. He tells another story about Michele Bachmann, a Tea Party star. After the Republicans won the House in 2010, she came to his office and demanded a seat on the most powerful committee, Ways and Means. Boehner told her she didn't have the seniority. Kevin: How did she take that? Michael: She threatened him. She said if she didn't get the seat, she would go on Sean Hannity, Rush Limbaugh, and every other conservative talk show and tell the world that Speaker Boehner was betraying the movement that gave him the majority. It was pure political blackmail. Kevin: What did he do? Michael: He outsmarted her. He knew she couldn't be on Ways and Means. But he also knew she craved legitimacy and importance. So he offered her a seat on the House Intelligence Committee instead. It's a serious, high-profile committee that requires secrecy and diligence. Kevin: A place where you can't just go on TV and spout off. Michael: Exactly. It was a brilliant move. She took the deal, and to everyone's surprise, she became a very serious, hardworking member of that committee. He channeled her energy from chaos into constructive work. Kevin: That's a rare win for the Mayor of Crazytown. But it sounds exhausting. It makes you wonder about the man himself. What kind of person willingly signs up for that job?

The Man Behind the Gavel: Principles, Personality, and Perspective

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Michael: That’s the final, and maybe most interesting, part of the book. Who is John Boehner? He constantly circles back to his upbringing. He was one of twelve kids in a two-bedroom house in Ohio. His dad owned a bar, Andy's Café. Kevin: And he worked there from a young age, right? Michael: From age eight. Sweeping floors, washing dishes, eventually tending bar. He says the most important lesson he learned there was that "Everybody who came through the door of Andy’s Café got treated the exact same way, no matter what they looked like, what they were wearing, or how much money they had to spend." Kevin: You can see how that would shape a political deal-maker. His instinct is to find the human connection, to treat everyone as a potential customer you can win over. Michael: Right. And it also explains his famous persona. The guy who loves golf, smokes cigarettes, and enjoys a glass of Merlot. He's unapologetically himself. There's a great story about him speaking at a press corps dinner where, because of ethics rules, they could only give him a gift worth less than ten dollars. Kevin: For a noted wine enthusiast, that's a challenge. Michael: So, on stage, they presented him with a bottle of MD 20/20, also known as "Mad Dog." Kevin: No they did not! That's hilarious. Michael: The audience roared. And Boehner loved it. He could laugh at himself. This persona, the "regular guy," was his anchor. It's why he famously said he'd rather cut his own grass and play golf than be president. It wasn't just a line; it was his core philosophy. He didn't have that all-consuming ambition that drives most top-tier politicians. Kevin: But that must have created a paradox. He's a regular guy who wants a simple life, but he's in this insane, high-stakes power game. How did he reconcile that? Michael: Ultimately, he couldn't. The breaking point, or rather the moment of clarity, came from a deeply personal and spiritual experience. For twenty years, he had been trying to get a Pope to address a joint session of Congress. He finally succeeded with Pope Francis. Kevin: I remember that. It was a huge moment. Michael: For Boehner, it was the pinnacle of his career. He's a devout Catholic. He met the Pope privately, and as Pope Francis was leaving the Capitol, he stopped, put his arm on Boehner's shoulder, and said, "Mr. Speaker, pray for me." Boehner just lost it. He started weeping. He said in that moment, he felt he had achieved everything he could. He had brought the Pope to Congress. What else was there to do? Kevin: So that was it? The high point from which he could gracefully exit? Michael: Yes. He said he went home that night, poured a glass of wine, and knew it was time. The very next day, he announced his resignation. He was leaving Crazytown for good.

Synthesis & Takeaways

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Kevin: It’s an incredible arc. From a bar in Ohio to the Speaker's chair, only to realize that the job had become impossible because the definition of politics itself had changed. Michael: I think that’s the core of it. The book is a time capsule. It’s a story from an institutionalist, a man who believed in the system, who found himself leading a party that was increasingly populated by people who saw the system as the enemy. Kevin: He was a deal-maker in an era that had stopped valuing deals. Michael: Precisely. And his whole philosophy is probably best summed up by one of his own "Boehnerisms" that he lists at the end of the book: "A leader without followers is just a man out taking a walk." By 2015, he realized the people behind him weren't following him anymore. They were running in a completely different direction, towards a cliff, and he had no desire to join them. Kevin: The memoir is, in a way, a cautionary tale. It’s a firsthand account of the political fracturing that led us to where we are today. It’s not just about Boehner; it’s about the erosion of a certain kind of politics. Michael: It’s a lament for a time when you could have a drink with your opponent, fight like hell on the House floor, and still find a way to get something done for the country. Boehner’s story asks if that time is gone for good. Kevin: That's the big, lingering question, isn't it? It makes you wonder, in today's political climate, could an old-school deal-maker like Boehner even get elected to Congress, let alone become Speaker? Or is Crazytown the new normal? Michael: A question to ponder over a glass of Merlot. Or maybe, just maybe, a bottle of Mad Dog 20/20. Kevin: I think I'll stick with the Merlot. Michael: This is Aibrary, signing off.

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