These letters are entirely imaginary—offered with wit, affection, and no partisan agenda. We hope they make you smile, make you think, and perhaps send you back to what the founders actually wrote.
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In our previous post, we learned what the Founding Fathers would think about the presidency. Today, Jefferson and Hamilton speculate about what would happen if America became a nation of great cities.
Source: The Jefferson-Hamilton Debates on Political Economy (1790–1792)
In their famous debates over the nation’s economic future, Jefferson championed an agrarian republic of independent farmers while Hamilton envisioned a commercial powerhouse rivaling European nations. Here, having glimpsed a future where most Americans dwell in vast metropolises, they resume their argument—each certain the other’s vision leads to ruin.
* * *
Monticello, October 14, 1792
Dear Madison,
I have had a most disturbing vision of America’s distant future, and I write to you in considerable agitation. I beheld our republic transformed beyond recognition—a nation where the vast majority of citizens dwell not upon the land but crowded together in cities of stupefying magnitude. Cities, Madison, containing not thousands but millions of souls, stacked upon one another in towers that scrape the very heavens.
Where in such warrens shall men find the independence that self-government requires? The farmer who owns his land answers to no man. But the city-dweller—what is he but a creature dependent upon others for his bread, his shelter, his very air to breathe? He purchases everything and produces nothing essential to his own survival. He is, in short, precisely the sort of dependent soul whom our ancestors would never have entrusted with the franchise.
I have long called cities pestilential to the morals, the health, and the liberties of man. What I saw suggests my fears were understated. When millions crowd together, vice multiplies, factions calcify, and the connection between citizen and soil—that sacred bond which anchors virtue—dissolves entirely.
Your alarmed friend,
Th. Jefferson
* * *
New York, October 28, 1792
Dear Sir,
Madison has shared your letter regarding this vision of urban America, and I confess I find your alarm somewhat theatrical. 
Consider: what are great cities but concentrations of human talent, industry, and exchange? The history of republics teaches that commercial centers have ever been the nurseries of liberty. Florence, Venice, Amsterdam—were these not freer than the feudal countryside surrounding them? The merchant who trades with the world develops habits of mind incompatible with tyranny: calculation, negotiation, the recognition that prosperity depends upon the rule of law.
Your farmer, whom you imagine so independent, is in truth subject to the tyranny of weather, isolation, and ignorance. He knows only what he sees. The city-dweller, by contrast, encounters ideas, compares opinions, and learns that reasonable men may differ. Is this not the very foundation of republican discourse?
Your obedient servant,
Hamilton
* * *
Monticello, November 12, 1792
Dear Hamilton,
You cite Florence and Venice as exemplars, but surely you recall how both ended—in tyranny and decay. Commercial republics generate wealth, I grant you, but they also generate the extremes of luxury and want that destroy republican virtue.
In the great cities I envisioned, I saw precisely this: wealth concentrated in towers of glass while multitudes crowded into squalid quarters, dependent upon wages that fluctuated with distant markets they could not comprehend. What ballot can a man cast freely when his very bread depends upon his employer’s favor? Your commercial paradise produces not citizens but servants—willing servants, perhaps, even comfortable servants, but servants nonetheless.
The farmer fails or succeeds by his own labor and God’s providence. That is liberty. The city-dweller rises or falls by currents he cannot see, much less control.
Ever yours,
Th. Jefferson
* * *
New York, November 26, 1792
Dear Sir,
You speak of the farmer’s independence, yet who cultivates your fields at Monticello? The contradiction escapes you, I think, because you imagine independence as a quality of station rather than of law. But true liberty resides in institutions, not in acres.
In great cities, men learn that their fates are bound together. They form associations, they petition, they organize. They discover that collective action can restrain the powerful more effectively than any individual’s stubborn isolation. Your farmer may answer to no man, but neither can he call upon any man’s assistance. The city-dweller may depend upon others, but he also has allies.
If America is destined to become a nation of cities, then let us ensure those cities have laws that protect the weak, institutions that check the powerful, and opportunities that reward industry. The alternative you propose—that all men must own land to be free—would leave most Americans forever unfree.
Your servant,
Hamilton
* * *
Monticello, December 10, 1792
Dear Hamilton,
You have touched upon a tender point, and I shall not pretend otherwise. But consider: if the cities you celebrate should cover the continent, where then shall the discontented go?
Perhaps your institutions will prove sufficient. Perhaps law can preserve liberty where land cannot. I confess I doubt it. But I concede this much: if America must become urban, then everything depends upon whether those cities are governed by citizens or ruled by interests. On that question, you and I might find common ground—however reluctantly.
Respectfully,
Th. Jefferson
* * * * *
If they only knew… that America would become the most urbanized nation in human history, with over eighty percent of its citizens dwelling in metropolitan areas. Jefferson’s agrarian republic is a memory; Hamilton’s commercial empire is reality. Yet the questions they raised—about dependency and dignity, about whether crowded millions can govern themselves, about where the discontented go when there is no frontier—remain as urgent as ever. The towers scrape the sky. The question is whether the citizens beneath them are free.
Questions for Reflection
Jefferson believed that only landowners could be truly independent citizens. In modern urban America, where most people rent rather than own, has his fear been realized—or proven wrong?
Hamilton argued that cities foster collective action and democratic participation. Do our modern cities unite citizens or divide them into isolated factions?
Without a frontier, where do Americans go when they seek a fresh start? Has anything replaced the frontier as an escape valve for discontent?
Share your thoughts in the comments—and if this made you think, please click ‘Like’!