Author Robert Caro uses a quotation attributed to the Greek playwright Sophocles as the epigraph of his monumental biography The Power Broker: Robert Moses and the Fall of New York1:
One must wait until evening to see how splendid the day has been.
It’s such a hauntingly perfect opening for that book. Caro uses it to masterfully frame Moses’s long career - how his early idealistic “morning” eventually gave way to a controversial and complicated “evening”.
The Master Builder # #
Robert Moses was the “master builder” of mid-20th century New York City and neighboring Long Island. As the shaper of modern New York, he is easily the most polarizing figure in the history of urban planning in the United States. Although he never held elected office, Moses was the most powerful person in New York City government from the 1930s to the 1960s. Operating through a complex network of public authorities that insulated him from democratic oversight, he constructed 627 miles of expressways, 13 bridges, and 658 playgrounds, as well as landmark achievements like Jones Beach and Lincoln Center.
Yet, despite all these achievements, he lived out his final years of life as a bitter and resentful man, isolated and removed from power. The final chapter of Caro’s book, titled “The Ghost Ship”, tells of a superannuated Moses visiting Jones Beach - the project he loved most of all. As he walked among the crowds of people enjoying the park he created, no one knew who he was. Why weren’t they grateful? The tragedy of the ending is that Moses lived long enough to see his “splendid day” turn into a cold evening where his accomplishments were taken for granted and his methods were loathed.
It is a devastating image to end on. Caro paints Moses as a man who fundamentally believed that the physical engineering of a city was the same thing as the social health of a city. By the end, he was essentially a king in exile within the kingdom he built.
The reason the public’s gratitude turned to resentment (and eventually hatred) boils down to three factors that Caro highlights throughout the book:
The human cost of “progress” # #
Moses’s philosophy was “When you operate in an overbuilt metropolis, you have to hack your way with a meat ax.” While he saw Jones Beach as a triumph, others saw the hundreds of thousands of people displaced by his expressways. He famously prioritized the automobile over the neighborhood. By the 1960s, the “urban renewal” that Moses championed was increasingly viewed as “urban removal,” particularly in low-income and minority communities like East Tremont in the Bronx.
The scale of his ego # #
The “Power Broker” was no longer building for the people; he was building for the sake of the power itself. Toward the end, his projects - like the 1964-1965 World’s Fair - were seen as massive, expensive ego trips rather than public utilities. The public sensed that Moses didn’t actually love the people of New York; he loved the idea of New York as a giant drafting board.
The shift in the cultural zeitgeist # #
Moses’s downfall coincided with the rise of Jane Jacobs and the grassroots movement to save local communities. The public’s values changed from a desire for “The Big Project” to a desire for “The Livable Street.” Moses was looking down at a 1920s dream of concrete and cloverleafs from his helicopter, while the people below were waking up to a 1960s nightmare of traffic, pollution, and lost heritage.
Why they weren’t “grateful” # #
In his mind, he had given the masses parks and bridges that would last centuries. He couldn’t understand why they cared about the “temporary” destruction of a few city blocks when he was building for the “permanent” glory of the city. He saw himself as a visionary surrounded by “small-minded” people who couldn’t see the horizon.
That ending underscores the tragedy of the Sophocles quote: his “morning” was defined by the brilliance of Jones Beach, but his “evening” was defined by the isolation of that final visit to the same park, realizing that he had built a world that no longer wanted him in it.
Sophocles’s warning crossed my mind the other day as I was skimming some technology news. The headlines were dominated by developments in artificial intelligence (AI) models, their ubiquity in the workplace, and the coming disruption for workers.
Most of the articles were evangelical in nature and I noticed that much of the excitement was based on hypothetical potentialities. Naturally, they all looked forward. It struck me that we are still in the promising “morning” of the Day of AI.
At the end of the lengthy introduction of The Power Broker, Caro says that it’s impossible to tell whether New York would be a better city if not for Robert Moses; he settles for saying that it would be a different city.
When considering the impact of AI, the reverse is true. There is no question artificial intelligence will make this world different from what came before. Ironically, it’s up to us - the humans - to determine whether, in the “evening”, the Day of AI has become a splendid one - or not.
As we do this, I think there are some lessons we should consider from the experience of Robert Moses.
What will be the human cost of “progress”? # #
This is the biggest question for me. In the workplace, many white-collar workers - including many of the AI evangelists - are about to realize, for the first time, that they are labor, as replaceable by AI as the factory workers replaced by automation.
For centuries, there has been a healthy tension between capital and labor. Despite different values and aims, both sides have needed each other to survive. In spite of the occasional lockout or strike, in the end both sides eventually find ways to work together for mutual benefit. Not because they want to, but because - to date - they have had to.
This tension may be permanently broken by AI, and to capital goes the spoils. White-collar or blue-collar, AI portends a situation where capital has an alternative to human labor. AI doesn’t care about working conditions, health care, or pensions. Why would capital bargain with human labor when they now have another option? Capitalism is not a moral system, and at that point, there is no incentive for capital to have any interest in the well-being of human labor at all.
Like Moses’s prioritization of automobiles over neighborhoods, capital’s incipient preference for AI over human labor has the potential to gut our workplaces as Moses gutted East Tremont for the Cross-Bronx Expressway. In America, where everything from health care to retirement benefits are tied to the workplace, this kind of disruption would be devastating. Think of the structural changes needed in American society to address that? Have you seen signs that we are prepared for anything of that scale?
The scale of ego # #
Moses eventually stopped building for New York and started building for Moses. The parks and bridges became monuments to his own power - Ozymandias in concrete. The World’s Fair of 1964 was the clearest expression of this: a massive, expensive spectacle that served no one’s interests but his own vanity and the illusion of his continued relevance.
The pursuit of Artificial General Intelligence has the same smell. AGI - a machine that can think, reason, and create at or beyond human levels across every domain - has become the animating obsession of the technology industry’s most powerful figures. But the honest question is whether this obsession is driven by humanistic purpose or by the oldest impulse in the history of powerful men: the desire to build something that will outlast them, something so large it cannot be ignored.
The resources being poured into AGI are not trivial. They represent choices - about what gets built and what doesn’t, about whose problems get solved and whose don’t. Moses chose the Cross-Bronx Expressway over East Tremont. The AGI race is making its own choices about what gets sacrificed on the altar of the monument.
The shift in the cultural zeitgeist # #
The technology industry was not always like this. I am old enough to remember the early Internet as a genuine act of faith - a belief that information freely shared would produce a more democratic, more connected, more humane world. That idealism was real, even if it was also naive. What replaced it was something much colder: platforms engineered for engagement rather than connection, personal data strip-mined for profit, and a systematic replacement of human judgment with algorithmic efficiency.
AI is arriving into that inheritance, and it is already beginning to displace the things we may find, in the evening, that we valued most. The writing, the image-making, the music - the things humans have always done to make meaning and to reach one another across the distances that separate us. These are not inefficiencies to be optimized. They are the point.
Moses believed that the physical engineering of the city was the social health of the city. He could not see the difference. There is a version of the AI future that makes the same category error - that optimizing for productivity and output is the same thing as flourishing. Jane Jacobs understood that a livable street was worth more than a fast one. The question for the evening of the AI day is whether we will arrive at the same understanding before too much has already been torn down.
“One must wait until evening to see how splendid the day has been.” How will we view AI at the end of its day? Will it carry through on the brilliant promise of its morning? Or will it, like Moses, exist in a world that no longer has a place for it?
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The Power Broker - a 1,286-page, four-pound volume - finally had a digital version released in 2025 in time for it’s fiftieth anniversary. As someone who lugged the physical book around when I first read it 25 years ago, I was particularly grateful for the e-book for last year’s re-reading. ↩