A City upon a Hill

Let’s take a quick detour from the usual VC topics to talk about something a bit older—400 years older, to be exact. It’s a Puritan text from Massachusetts, which makes it perfect for Thanksgiving. (Yes, I know the Puritans aren’t the same as the Pilgrims. Stick with me here.)

This text has echoed across centuries, its meaning changing in fascinating ways. And it offers an unexpected window into today’s debates over original versus traditional meaning.

You’ve probably heard American leaders refer to the United States as a “shining city upon a hill.” The phrase became a political staple thanks to Ronald Reagan in the 1970s and 80s. But Reagan didn’t invent it. He borrowed it from John Winthrop, the 17th-century governor of the Massachusetts Bay Colony, who got it from the Gospel of Matthew.

Winthrop used the phrase in 1630 in an essay titled A Model of Christian Charity. He wrote it either onboard the Arbella on his way to America or just before leaving England—historians aren’t entirely sure. His goal? To describe the high stakes of the Puritans’ mission in the New World. “For we must consider that we shall be as a city upon a hill,” Winthrop wrote. “The eyes of all people are upon us.”

The idea of America as an exceptional, world-altering place has stuck with us. But, as I discuss in a recent Legal Spirits podcast with Notre Dame historian Don Drakeman, the meaning of “city upon a hill” has changed dramatically.

For Reagan, Winthrop was a “freedom man,” and the city symbolized a refuge for people seeking freedom. Reagan’s version wasn’t just about liberty, though; it was a point of national pride. He described the city as “a tall, proud city built on rocks stronger than oceans, wind-swept, God-blessed, and teeming with people of all kinds living in harmony and peace.” It was a place of open doors, bustling commerce, and boundless opportunity.

It’s a nice image—but totally unlike the original. True, Winthrop and the Puritans sought freedom, but not in Reagan’s sense of commerce and individual liberty. Their vision was static, hierarchical society, united by Christian love. They weren’t tolerant of religious disagreement and would not have seen intolerance as a failing. All kinds of people? They didn’t even welcome other English Protestants.

And Winthrop’s “city upon a hill” wasn’t a boast—it was a warning. If the Puritans failed to uphold their covenant with God and show Christian love, their mission would fail. They wouldn’t be a shining example. They’d be a cautionary tale, “a story and a by-word through the world.”

Just now, constitutional scholars are debating the difference between original and traditional meaning. A Model of Christian Charity isn’t a binding legal text, of course, but it seems to me it offers a nice example of the issues in the constitutional debate.

Think of A Model of Christian Charity as expressing the “original meaning.” Winthrop’s understanding is clearer than many original meanings, in fact. The Reagan-era version—the one most Americans know today—represents the “traditional meaning” that’s evolved over time. And that meaning itself is 50 years old—which is reasonably old, in a country that dates back only 250 years.

So, which one is “correct”? The original meaning, or the meaning Americans have come to understand over time?

I dig further into all this in my recent Legal Spirits episode with Don Drakeman. You can check it out here.

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