The Highwayman (Part 1 of 3)

Core idea

The Highwayman is Caro's account of Moses's single most consequential decision: in the postwar period, with federal money flooding into urban infrastructure and the option open to build either highways or mass transit, Moses chose highways. He chose them over the objections of transit experts, against the recommendations of the Regional Plan Association, in defiance of the dominant European urban-planning trend. The choice locked New York into automobile dependence for the rest of the century. The topic's title — Highwayman — registers Caro's verdict.

Why it matters

The postwar choice

After WWII, with the auto industry back at full production and federal money pouring into urban infrastructure, every American city faced the same choice: highways or mass transit. European cities chose transit; American cities mostly chose highways. New York's choice was Moses's; he committed the metropolitan region to automobile dependence for the rest of the century.

The path not taken

Caro lays out the alternative: federal money could have funded the long-proposed Second Avenue Subway, trans-Hudson rail tunnels, and Long Island Rail Road modernization. The Tri-State region could have had what European regions have today: integrated rail with parkway and bus right-of-way. Moses chose to spend the same money on highways instead. The path was not unavailable; it was rejected.

Key takeaways

Mental model

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Practical application

Example

Modern urban planning choices in cities like Atlanta and Houston between 1960 and 2000 made versions of the same Moses choice — highway expansion over transit investment. Each rejection of transit was specific; each set the city's path for a generation. The pattern is consistent.

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