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Robert Caro’s The Power Broker (Abridged)

The First Article in The Power Broker Excerpt

To me, reading The Power Broker by Robert Caro always seemed like an intellectual bullying move. There are some of us that can’t get through a 1344-page book, no matter how hard we try. It’s just not going to happen. Even the audiobook clocks in at 66 hours long.

On the other hand, it sounds like an awesome book. Barack Obama and Conan O’Brien call it their favorite book. One of my favorite podcasts, 99% Invisible, even ran a book club on The Power Broker, using it to unpack how power quietly shapes cities. Guests included The Good Place creator Michael Schur, former U.S. Transportation Secretary Pete Buttigieg, and even Caro himself. The New Yorker even published a satire piece on this phenomenon.

I’d resigned myself that I was never going to get to it. But then I discovered that the book was serialized into a series of articles in The New Yorker. These articles appeared in the issues in the summer of 1974. True to form, this was one of the longest serializations, broken up into 4 pieces for a total of 79,000 words—the length of a substantial book:1

  • “The Best Bill‑Drafter in Albany”, July 14, 1974
  • “If the End Doesn’t Justify the Means, What Does?”, July 21, 1974
  • III: “How Robert Moses Got Things Done”, August 4, 1974
  • IV: “Point of No Return”, August 11, 1974

Reading these articles, I realized that Robert Moses didn’t just shape New York—he built it. Every time I drive around the city, I find myself asking: How did all these roads get here? I understand the Manhattan grid of the early 1800s, but what about the highways, bridges, and parkways? None of them have changed in my lifetime, yet most were built only after the automobile arrived around 1900. The answer, it turns out, is Robert Moses. As Caro says in the introduction:

Standing out from the map’s delicate tracery of gridirons representing streets are heavy lines, lines girdling the city or slashing across its expanses. These lines denote the major roads on which automobiles and trucks move, roads whose very location, moreover, does as much as any single factor to determine where and how a city’s people live and work. With a single exception, the East River Drive, Robert Moses built every one of those roads. He built the Major Deegan Expressway, the Van Wyck Expressway, the Sheridan Expressway and the Bruckner Expressway. He built the Gowanus Expressway, the Prospect Expressway, the Whitestone Expressway, the Clearview Expressway, and the Throgs Neck Expressway. He built the Cross-Bronx Expressway, the Brooklyn-Queens Expressway, the Nassau Expressway, the Staten Island Expressway and the Long Island Expressway. He built the Harlem River Drive and the West Side Highway.

Only one borough of New York City—the Bronx—is on the mainland of the United States, and bridges link the island boroughs that form metropolis. Since 1931, seven such bridges were built, immense structures some of them anchored by towers as tall as seventy-story buildings, supported by cables made up of enough wire to drop a noose around the earth. Those bridges are the Triborough,[*] the Verrazano, the Throgs Neck, the Marine, the Henry Hudson, the Cross Bay and the Bronx-Whitestone. Robert Moses built every one of those bridges.

Scattered throughout New York stand clusters of tall apartment houses built under urban renewal programs and bearing color, splashed on terraces and finials, that in the twentieth-century American cityscape marks them as luxury dwellings. Alongside some of these clusters stand college lecture halls and dormitories. Alongside one stand five immense dingy white expanses of travertine that are Lincoln Center, the world’s most famous, costly and imposing cultural complex.

Caro, Robert A. The Power Broker: Robert Moses and the Fall of New York.

This doesn’t even mention the 148,000 apartments and 600+ playgrounds. That’s why this cartoon, from this summer, is still so relevant:

New Yorker Cartoon, Emily Berstein, July 28, 2025

Caro spent seven years researching The Power Broker. Remember, this is a man who has only written two major works in his life—the other being his still-unfinished, multi-volume authoritative biography of Lyndon B. Johnson. Caro was such a relentless researcher that Robert Moses stopped speaking to him after Caro began asking pointed questions that challenged Moses’s official narrative.

Caro carefully unfolds the history of these projects. One of my favorites is how suburban Long Island exists largely because Robert Moses wanted to get New Yorkers to the beach. In the 1920s, when he was Parks Commissioner, Moses envisioned a vast network of beaches and parks—Jones Beach, Sunken Meadow, Hither Hills—that would offer working-class city residents a democratic escape from the sweltering, crowded tenements of New York. But the problem wasn’t just building the beaches—it was getting people to them. So Moses didn’t just build parks; he built the parkways to reach them. With meticulous strategy, he secured funding, dodged political opposition, and used obscure legal provisions to seize and rezone land for long, scenic highways like the Southern State, Northern State, and Wantagh Parkway. These roads weren’t just infrastructure—they were invitations.

Once the highways were built, people flooded out of the city in their cars, and where they stopped for recreation, they eventually stayed to live. The desire to reach the beaches started a new pattern of suburban growth. Moses didn’t just give New Yorkers access to sand and surf; he redrew the map of where people could imagine their lives unfolding. What began as a public amenity strategy became the foundation for postwar suburban expansion—sprawling communities along the corridors that led to the coast.

It’s written with the pace and drama of a novel, but at heart it’s a tragedy. Caro structures The Power Broker like the story of a fallen hero—someone who begins as an idealist and ends as a cautionary tale. In the early chapters, Moses is a sympathetic character: a brilliant reformer who wants to clean up the graft and inefficiency of Tammany Hall, a man who genuinely believes parks and public works can ennoble a city. But as his power grows, so does his arrogance. The same moral certainty that fueled his reforms hardens into something darker.

Caro captures this transformation as a novelist would. The idealist who once built Jones Beach so ordinary New Yorkers could see the ocean becomes the autocrat who lowers the parkway bridges so buses—and thus poor and Black families—can’t reach it. The planner who once dreamed of playgrounds for children ends up bulldozing their neighborhoods to make way for expressways. By the time he’s slicing the Cross Bronx through the heart of working-class communities, he’s stopped seeing citizens at all—only obstacles.

The only problem with the book is that it’s too powerful—and for decades, it’s been almost the only story we have about Moses. Written in the spirit of the 1960s and ’70s Jane Jacobs movement, it reflects a moment when the tide had turned against Moses’s brand of top-down modernism. By then, expressways had become symbols of destruction, not progress, and the neighborhood voices Moses once ignored were finally being heard. Caro channels that spirit, using Moses as both subject and warning: the man who thought he was saving New York by remaking it in concrete and steel was, in Jacobs’s eyes, dismantling the very fabric of the living city.

The book uses Moses as the embodiment of an entire era—making moses into a villain. Caro channels all the arrogance, blindness, and hubris of mid-century modernism into a single man, as if Moses alone poured the concrete and cleared the neighborhoods. But Moses wasn’t acting in a vacuum—he was the product of a culture that worshiped progress, trusted technocrats, and believed problems could be solved by building something big. By personalizing that system, Caro gives us a gripping story, but also a convenient scapegoat. The real story isn’t just about Robert Moses; it’s about everything going on at that time.

And there’s a larger problem: there’s really only one major book about him—and it’s a 1,344-page tome. While the book offers different sides of Moses, there’s only one theory of the case, and it’s from Caro. His Moses—the brilliant tyrant who built New York and broke it in the same breath—became the definitive version. Over time, that version hardened into truth.

When The Power Broker came out in 1974, New York was falling apart—graffiti on the subways, crime in the headlines, garbage piling up on the sidewalks. The city that had once believed it could build its way into the future was now on the verge of bankruptcy. Caro’s book didn’t just tell the story of Robert Moses; it told the story of a whole generation. It gave shape to what people were already feeling—that the modern world, with all its glass towers and expressways, had failed them. The Power Broker offered them an explanation.

So even reading the entire book doesn’t give you the whole story. Paul Goldberger, the architecture critic for the New Yorker, adds some crucial context. Goldberger reminds us that Moses wasn’t some rogue genius operating outside his era—he was his era. Every major American city in the mid-century was tearing itself apart in the name of progress, trading subways for expressways and neighborhoods for parking lots. Moses just did it bigger, faster, and more visibly than anyone else. To say he single-handedly ruined New York is to miss the deeper truth: that he was the clearest expression of what America believed at the time—that the future could be engineered. Goldberger writes that “Moses didn’t bring down New York, and he didn’t single-handedly sell its soul to the automobile. Indeed, New York probably comes closer to having a workable balance between cars and mass transit than any other city in the country.”2

I’m so glad that I finally got to read The Power Broker, in its abridged form. It is a phenomenal book, full of history, drama and intrigue. But the book needs to be read in context. The book’s subtitle, “Robert Moses and the Fall of New York,” doesn’t really ring true 50 years later. We wouldn’t have the Triborough Bridge or the Long Island Expressway. We wouldn’t have Long Island as we know it today.

For me it’s personal. Moses bulldozed working-class neighborhoods to build Lincoln Center, which jumpstarted the redevelopment of the Upper West Side—the theaters, restaurants, and brownstones that define it today. As part of that transformation, he built our apartment building in Lincoln Towers. I owe my home, my kids’ elementary school down the block, and the neighborhood I love to Robert Moses.

Footnotes

  1. I was able to download the PDFs from the New Yorker digital archive from the New York Public Library. ↩︎
  2. Paul Goldberger, “Eminent Dominion: Rethinking the Legacy of Robert Moses,” The New Yorker, February 5, 2007. ↩︎
Categories
Books / Audiobooks Media

Revisiting Truly Tasteless Jokes

The First Book of the Series

Why does my son watch these horrible Instagram influencers who spew misogyny, racism, and hate? There’s Andrew Tate, arrested on human trafficking charges. And Dan Bilzerian, who literally threw a porn star off a roof. I want to yell that my generation was different, that we were better, that we never fell for such garbage.

But then I remembered Truly Tasteless Jokes.

I was thirteen when someone passed me the book on that long bus ride from camp to Hershey Park, and I knew I was holding something special. It was a secret portal into adult humor—the kind of stuff that would get you grounded just for knowing it existed. This was the 1980s, that lawless time before warning labels. No gatekeepers, no protection—just forbidden fruit waiting to corrupt curious kids like me.

We’d huddle around our contraband. If you were there, you remember the jokes. If not, they’re too tasteless and horrible for me to print here. We’d memorize them and trade them like baseball cards, each one more shocking than the last.

It was taboo. It was like looking at dirty magazines, but somehow more accessible because they were just books in the bookstore. Just an aisle away from the Nancy Drew books. What I didn’t understand then was that this wasn’t just some random collection of offensive humor—it was a cultural earthquake.

A Cultural Phenomenon

Truly Tasteless Jokes wasn’t just an offensive book series. It was a legitimate cultural phenomenon. At one point, Blanche Knott had four books on the New York Times bestseller list simultaneously—the first time that ever happened.

The books were so popular that more respectable authors and publishers complained that the New York Times bestseller list was being defiled. This led to the creation of the “Advice, How-to and Miscellaneous” category on the bestseller list.

Looking back, Truly Tasteless Jokes was a product of its cultural moment. The 1980s were Reagan’s America—a deliberate rejection of the political correctness of the 1960s and 70s. As cultural critic Luc Sante observed, they were “a sigh of release, a sign that we weren’t living in the politically correct Sixties and Seventies anymore, and could behave like pigs if we wanted to.”

It was the original anti-PC phenomenon, a middle finger to civil rights progress and social consciousness. The jokes weren’t just offensive—they were intentionally, aggressively offensive. They were a backlash.

The Woman Behind Blanche Knott

The author on the cover was listed as Blanche Knott. I’d always thought this was a female pen name for a male syndicate who wrote the books—like Franklin W. Dixon was to the Hardy Boys. But the books, including dozens of sequels, had a single author—the improbably named Ashton Applewhite..1

Applewhite was an underpaid assistant editor at St. Martin’s Press, earning just $8,500 a year while writing book jacket copy. Between assignments, she collected offensive jokes on cocktail napkins and “While You Were Out” slips, stuffing them into her desk drawer. Her original title was her favorite joke: What’s the Difference Between Garbage and a Girl from New Jersey? The punchline: garbage gets picked up.

When the manuscript first made the rounds, one editor at Penguin said, “If we published this, the little bird would have to hide its head under its wing in shame.” A woman at another publisher told the agent, “We can’t publish this here. I’m not even sure we can Xerox this!”

But Ballantine did publish it. And America spoke—loudly, to the tune of millions of copies. It sparked copycats and even a VHS tape. The tape is fairly lackluster; however, it does include early clips of Andrew “Dice” Clay, who perfectly captured the spirit of the jokes in the book.

The Reckoning

There are different ways to look at the legacy of Truly Tasteless Jokes. The documentary Tasteless featured comedians defending the book and comedy in general, even when it sometimes hurt people, positioning it as a fight against cancel culture, with performers arguing that humor serves as a necessary release valve for society’s tensions.

Contrast that with the Decoder Ring podcast, where the host insisted on highlighting how awful the book was and demanded that Applewhite apologize for writing it—which she eventually did. While the impulse is understandable—these jokes are horrible—there was something deeply counterproductive about the whole exercise. The host was so focused on moral purity, so determined to distance herself from the content, that she completely missed the point.

That kind of heavy-handed liberal righteousness, that desperate need to prove you’re on the right side, that reflexive “you can’t talk about that” energy—that’s exactly what caused this phenomenon to emerge in the first place.

Going Forward

Here’s the thing about teenagers and offensive content: they’re going to find it. Whether it’s Truly Tasteless Jokes in the 1980s or Andrew Tate on Instagram today, kids are drawn to transgression. They want their forbidden portals into adult humor and adult rebellion.

The question isn’t how to eliminate that impulse—it’s how to channel it constructively. When we create an environment where certain thoughts and jokes are so forbidden that they can’t even be discussed, we don’t make them go away. We just make them more powerful.

We need to resist the urge to sort everything into neat moral categories—good or evil, acceptable or unacceptable, worthy of cancellation or worthy of praise. Real people are messy. Real growth happens in the gray areas. When we demand that everyone meet some impossible standard of moral purity, when we insist that past mistakes define present character, we’re not creating a better world. We’re creating a world where we’re terrified of authenticity, and growth becomes impossible.

Footnotes

  1. Applewhite tells her story in Being Blanche, a 2011 Harper’s Magazine piece that’s worth tracking down. The article is paywalled, but most libraries provide digital access to Harper’s archives—and it’s an incredible read that reveals the woman behind the phenomenon. ↩︎

Categories
Books / Audiobooks Life Lessons

A September 11th Memorial: Firehouse

Every September 11th, the memories return: the falling towers, the smoke, the senseless loss. This year, I discovered it just a block from my apartment, in the pages of David Halberstam’s Firehouse—written by a neighbor I’d never met.

Halberstam, the Pulitzer Prize-winning author, lived nearby and was searching for meaning after September 11th, just as I am now. He spent two and a half months with our local firehouse to write a memorial not just to the firefighters who died that day, but to the firehouse itself and to all the firefighters in New York.

On that day, the New York Fire Department lost 343 men. Our firehouse lost two entire companies—the 12 men of Ladder 35 and Engine 40—one of the worst losses in the city.

Halberstam takes us inside the firehouse, into a culture normally kept private. It’s an insular brotherhood of men who eat together, live together, play sports together, and help repair each other’s houses. While we see the public face of firefighters—the men running into the Twin Towers when everyone else ran out—we rarely see what lies beneath. As Ray Pfeifer, a veteran of the firehouse, says, “People think they know what we do, but they don’t really know what we do.” They don’t understand the real danger of being in a burning building when there’s a collapse and the exits seem blocked.

The swagger of a firefighter isn’t arrogance—it’s earned. Take the captain’s code: first in, last out of every fire. It’s a point of pride that sets them apart, especially from police officers. While cops climb the ladder toward desk jobs and safer assignments, firefighters advance toward greater danger—lieutenants get closer to the flames than probies, captains closer than lieutenants. It’s a confidence born from their unique relationship with risk, which explains the firehouse joke: “If firefighting were easy, the cops would do it.”

“I have always admired acts of uncommon courage on the part of ordinary people,” Halberstam writes comparing them the heroes of the Civil Rights movement and the Vietnam War that he covered decades earlier. They live in a world of good and evil, where the good guys fight against a purely destructive force. As Angie Callahan, the wife of fallen Captain Frank Callahan, said, “Where else can you be brave in a time of peace, and where else can you do things that few other men do—deeds that save lives?”

To give you a taste of the book, here’s how Halberstam describes Captain Frank Callahan and the two traits that define great firefighters: staying calm and doing the right thing.

Wherever the fire was, though, he was very good at it. Very professional, and very calm. Calm was important; it was one of the most important words in the vocabulary of firemen, and a word they did not use lightly. That and the phrase “do the right thing,” as in, “He was the kind of fireman who always did the right thing.” Staying calm for a fireman was crucial—for unlike most other peacetime jobs, firemen were in the regular business of the suppression of fear. Every call might be a ticket to a burning inferno where there was no light, where falling walls and ceilings cut off exit routes, where a floor could give out, and where a fireman could become disoriented and begin to feel his source of oxygen failing as he grew weaker and as the heat grew more fierce second by second. Therefore keeping calm was a critical part of the job. Every serious fire could trigger powerful impulses of fear, and if an officer shows that fear on the job, if he is not calm and not disciplined himself, then the fear will spread quickly through the men. Calm is the most basic of the positive words that firemen use to describe one another.

David Halberstam, Firehouse

It’s a mindset most of us can’t imagine—being paid to suppress fear while everyone else is allowed to feel it.

Doing the right thing was equally important. When the men speak of a colleague who does the right thing, they mean he will stay at his post under terrible conditions and not panic. Doing the right thing was going in and risking your life for a trapped civilian or fellow fireman. Firemen define each other by their codes of honor, which, because of the nature of the job, are mandatory and must be instinctive.

David Halberstam, Firehouse

But Halberstam reveals that heroism in a firehouse isn’t just about the dramatic moments. It starts with something as simple as washing dishes:

The men have to be able to count not just on their officers, but on their buddies. Doing the right thing also involves small, seemingly unimportant things in the firehouse. It begins when you are a probie, and it means following certain customs, such as being the first one to the sink to wash the pots and pans after meals. The firehouse, like the military, is based on doing little things right, because if someone does not do the little things correctly, then he probably won’t do the big things correctly. Moreover, in a firehouse, if you do not do your share of the routine work, someone else has to do it for you, in which case you pull down the house, and you are a hairbag. You do not wait for someone to tell you to do it, you just do it. There is an additional reason: Between moments of fearsome danger, there is often a lot of slack time at a firehouse, and if you do not have codes like this, then it would be very easy for people to become lazy and get in a rut, and for the entire house to lose its sense of cohesion and its purpose.

David Halberstam, Firehouse

This September 11th, I’m thinking less about the towers that fell and more about the men who ran toward them. Halberstam’s Firehouse reminds us that heroism isn’t reserved for history’s darkest moments—it’s practiced daily by ordinary people who’ve chosen extraordinary lives. They’re still out there, still running toward danger, still doing the right thing.

The inside covers of Firehouse feature black and white photographs of the chalkboard frozen in time—exactly as it appeared on September 11th.
Categories
Books / Audiobooks Writing

A Short History of Thinking on Paper

I love notebooks.

I love the ritual of pulling out my Leuchtturm Bullet Journal and pretending—for a few minutes each day—that I’m a nineteenth-century poet in a French cage, writing up my deep and progound thoughts. Most of the time, it’s my work list and reminders for my kids’ homework. But still.

I like that I can carry a physical artifact of my thoughts. That I can plan my day in a truly analog fashion. That I can step away from screens and write things down, slowly, by hand.

In a world where it’s normal to carry around a supercomputer in your pocket, a notebook starts to feel like an extravagance. A tiny luxury. Which is strange when you think about it. The iPhone is a thousand dollars. But it’s the twelve-dollar notebook that feels indulgent.

That’s why I was so excited to stumble across The Notebook: A History of Thinking on Paper by Roland Allen.

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Books / Audiobooks

Joe Biden’s Original Sin

I just finished Original Sin, the book by Jake Tapper and Alex Thompson that traces how President Biden’s decision to run for a second term—despite mounting evidence to the contrary—slowly unraveled into a crisis. It’s not a thriller, exactly. More of a slow-motion reckoning.

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Books / Audiobooks Meditation

Finding Walden: How a 19th-Century Hipster Taught Me to Pay Attention

How I Think Thoreau Woud Look If He Lived Today

When I tell people I’m re-reading Walden, they usually look at me a little funny. There’s a certain kind of surprise that comes with it—Wait, that book? The one everyone had to read in high school? The one where the guy builds a cabin and creates war stories about ants?

And I get it—Walden is an odd book. It’s undeniably important in the American literary canon, but it’s tough to get through it with that mindset. The first couple of times I picked it up, I tried to absorb every sentence as if each one held some hidden truth. That didn’t work. I stalled out somewhere in the bean field chapter, buried in Thoreau’s painfully detailed accounting of rows, yields, and the price of beans.

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Books / Audiobooks ChatGPT

The Power of the Written Word

I’m pissed. Bestselling nonfiction books have been lying to me. I know I shouldn’t care so much about this, but these books hold an odd level of cachet in our world. Books like those by Steven Levitt (Freakonomics) or Malcolm Gladwell (Outliers) have ideas that I used to take seriously. But seem to go viral throughout culture, shaping the way we think and talk about the world.

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Books / Audiobooks

Yale Needs Women

This year, Yale honored Constance L. Royster ’72, the second Black woman to receive the Yale Medal (as far as I can tell), the university’s highest alumni honor. Ms. Royster was celebrated for her extraordinary contributions to Yale—her dedication, her advocacy, and her unwavering commitment to building a stronger, more inclusive community.

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Adventures Books / Audiobooks

How John Harrison Stole the Longitude Prize

On my trip to the Royal Observatory in Greenwich, I learned about how important time was for navigation. In the 1700s, sailors had no reliable way to determine their exact position at sea, which often led to ships being lost and many lives being endangered. The primary challenge was determining longitude, as latitude could be measured with relative ease using the stars.

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Books / Audiobooks

The Language Hoax

In his book The Language Hoax, John McWhorter writes about one of the longstanding myths in linguistics: Language influences and defines the way that people things. Like his other books, McWhorter writes about how focusing too much on the differences in language is an excuse for the elite to look down upon others.