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Interview·March 28, 2026·6 min

A Conversation with Henry Ashford

On writing 250 stories in two years, the year he almost quit, and why he kept Frederick Douglass's 1852 Fourth of July address open on his desk throughout.

by the editors

A note from the editor

This conversation took place over two afternoons in late February in the front room of Henry Ashford's house in western Massachusetts. Henry has written or co-written roughly two hundred and fifty essays, dispatches, and reviews for various publications since 2023, most of them on American political and intellectual history. He agreed to talk on the condition that he wouldn't be asked about his own work in the abstract — only about specific pieces. We mostly held to that. — The Editors


You said in an email that you almost quit in late 2024. What happened?

I had been writing a long piece on the Reconstruction Amendments and I lost it. Not metaphorically — I lost the file. I had been working in a draft folder that synced badly across two machines, and a version-control conflict ate about eleven thousand words of work I had been doing for six weeks. I had no backup. I had been telling myself I would set one up "this week" for, I think, three months.

I don't tell that story to make a point about backups. I tell it because what happened next surprised me. I expected to be furious. I was, for about an hour. And then I sat down at the kitchen table with a yellow pad and tried to remember what the argument had been, and I realized I couldn't. Not the structure of it. Not the conclusion. I could remember sentences. I could remember footnotes. I could not remember why I was writing it.

That was the moment I almost quit. Not the losing of the file. The realization that I had been working on a piece for six weeks without being able to state, simply, why it needed to exist.

Did you go back to that essay?

I never wrote it. I wrote a much shorter piece — about four thousand words — that addressed one specific question: why the Fourteenth Amendment's Section 3 has been so rarely litigated. That piece took me eight days. It was much better than the lost one.

What I learned, or relearned, is that length is a temptation. The longer a piece gets, the more it feels like the writer is doing serious work. Usually what's actually happening is that the writer doesn't know what the argument is yet and is hoping the words will figure it out.

You write fast. Two hundred and fifty pieces in two years works out to a piece every three days. How?

It's not actually two-fifty long-form essays. About half are short dispatches — eight hundred to twelve hundred words, written in a sitting. Another quarter are book reviews, which have a strong external structure: the book gives you your scaffolding, and you fill in the response. Maybe sixty are the long things. The long things take real time. None of them takes less than three weeks.

The volume is possible because I don't have other hobbies. I'm forty-seven. I read for about three hours every morning and write for about four hours every afternoon. I don't watch television. I see friends on weekends. That's the whole life. It's a perfectly defensible one and I would not recommend it to anyone under thirty-five.

What's on your desk right now?

A copy of John Hope Franklin's From Slavery to Freedom, the eleventh edition. Eric Foner's The Second Founding. A library copy of Annette Gordon-Reed's The Hemingses of Monticello that is now nine months overdue and which I have paid the fine on three times. A printout of Frederick Douglass's "What to the Slave Is the Fourth of July?" — the 1852 Rochester address — which has been on my desk for the entire year I have been doing this work. I refer to it constantly. There is a passage near the end where Douglass quotes Isaiah and then says, simply, that "the conscience of the nation must be roused." I have started using that as a kind of touchstone. When I'm writing about something American and I cannot say what conscience I'm trying to rouse, I know I haven't found the piece yet.

Why that speech, specifically?

Because it is the most honest piece of American political writing I know. Douglass had been invited by the Ladies' Anti-Slavery Society of Rochester to give a Fourth of July oration. He showed up on July 5 — he wouldn't speak on the 4th itself — and delivered an address that praised the Founders, situated himself respectfully in the American tradition, and then said: "This Fourth of July is yours, not mine."

It is the perfect demonstration that you can love a country without flattering it. Or, more precisely, that loving a country requires refusing to flatter it. The speech is patriotic and devastating at the same time, in a register American political prose has almost completely lost.

When I'm writing about, say, the Federalist Papers, or about the founders, or about any of the inherited materials of American politics, I try to ask what Douglass would say. Not in a performative way. As a check on sentimentality. Most of what's written about the founding right now is too sentimental in one direction or the other — either hagiography or denunciation. Douglass managed to do something harder. He managed to be honest.

Most of the essays Bay Path publishes are about the founding and the nineteenth century. Why not more on the twentieth?

A few reasons. The first is that I have less to say about the twentieth century than I'd like to. The second is that the twentieth century is so over-written that it's hard to find an angle that doesn't feel like a rehearsal of a debate someone else already won. The third is that the nineteenth century is where the United States made most of the choices it is currently living with — about race, about industry, about empire, about the structure of its constitutional politics — and we have not finished metabolizing what was decided then.

When I started this magazine, I wanted it to be a place where you could read serious essays about American history without feeling like you were being recruited to a side. I'm not sure how successful I've been. I do know that almost every issue's mail is split fifty-fifty between readers who think I'm too critical of the founding and readers who think I'm too admiring. I take that as a sign I'm in roughly the right place.

What's the year ahead?

I'm working on a long thing — and I mean long, six- or seven-part — on the politics of the Reconstruction Amendments and how they were undone. I'm reading a great deal of Foner and a great deal of Gordon-Reed and a great deal of the Slaughter-House Cases and United States v. Cruikshank. I expect the first installment to appear in late summer.

I'm also trying to teach myself enough about the colonial period to write something credible about it. I have always been weakest before, roughly, 1763. I have a stack of Pauline Maier next to my reading chair.

Last question. If you could put one paragraph on every American reader's desk, what would it be?

The closing of Lincoln's First Inaugural. The mystic chords of memory passage. Not because it's the most profound thing he wrote — it isn't — but because it is the most generous. He is speaking to people who are about to try to kill him. He is asking them to remember that the country is made out of memory. He is making, in real time, the argument that political community is sustained by an act of attention to what came before.

I think that's the work American writing is supposed to do. Pay attention to what came before. Don't flatter it. Don't burn it. Hold it open.

the editors writes for Bay Path Press.
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