Decoding an Ancestor’s Scandalous, Encrypted Diaries

It was more than five years ago when I first heard Jeremy B. Jones talk about the journals of William Thomas Prestwood. By many accounts, Prestwood might be considered a nineteenth-century everyman—except for a handful of facts. First, Prestwood recorded daily accounts of his life, and those journals miraculously survived almost two hundred years. Second, some of the events Prestwood recorded were a series of sexual relationships that seem scandalous even by current standards. Third, Prestwood attempted to keep his journals secret by encrypting them in his own invented code. But the final fact that drew Jones to this man who almost disappeared into history was that Prestwood was Jones’s great-great-great-great grandfather.

From Prestwood’s salacious appetite for women to the fortuitous way his code was deciphered,  the narrative in Jones’s new memoir, Cipher: Decoding My Ancestor’s Scandalous Secret Diaries, is fascinating. So, too, is the sense of place that’s integral to much of Jones’s work. But what resonates even more is the unique way Jones holds his forefather’s life from the nineteenth century as a mirror to better understand his own existence in our also complicated twenty-first century. 

Cipher is especially timely in this moment that finds our nation so deeply divided. Prestwood lived during the tumultuous time between the founding of the United States and the Civil War. Using Prestwood’s journals as a catalyst, Jones reflects on how questions of masculinity and racial equality still drive our politics and culture. And yet, Jones’s journey is intensely personal as he seeks to be a good father raising his sons into good men. 

Jones and I connected over a series of emails, in which we discussed the process of journaling, what it’s like to be haunted, and whether the past offers any hope for our current times.

Denton Loving: Cipher is an exploration of history—your personal history, your family’s history, and the history of our country. But you also approach your subject from a host of different angles such as science, genetics, and encryption. How do you juggle all of that, both when you’re drafting and when you’re revising?

Jeremy B. Jones: You take ten years to write a book, that’s how. I struggled for a long time to find a shape for Cipher. It started as a long epistolary essay. Then I converted it to a collection of essays. Then I tried dividing it into thematic sections. A lot of the work to find a suitable form was, of course, also me trying to make sense of the content. I needed to figure out what I thought in order to figure out how to arrange it. Ultimately, I found that the more I researched, the more a potential shape appeared, and in the end, the idea of a double helix took hold for me. I conceived of the book as a winding together of my ancestor’s story and mine, each of our strands wrapping around the other. This structure began to tease out connections and parallels between our lives and other subjects that I only sensed at first but then began to find a way into. And because his story is naturally vulnerable—he never expected anyone to decode and read his diaries—my story was pulled in that direction, too: I figured I owed him to be honest and forthright about my life.

DL: What would William think about your extensive interest in his life? What would he think about others reading about his life two centuries later?

JBJ: I’d like to think I know him pretty well after all this time with his recorded life, and yet, I’m not sure what he’d think about the attention. My suspicion is that he’d think it a waste of time. In a list of advice to his sons he writes, “There is more pleasure in private than public life.” It’s clear from his diaries that he never tried to make a name for himself, not in any major way. It is, in fact, a frustration that the codebreaker has. In the codebreaker’s notes, it’s clear he thinks that William is a “remarkable human . . . who never put himself forward.” Afterall, William spent his days dissecting animals and experimenting with atmospheric forces and charting planetary orbits and reading texts in Greek and Latin and inventing new surveying tools. In the codebreaker’s view, William could’ve been an important historical figure had he made an effort. I think, however, that William understood the value in living a contained, simple life. A private life. Because of that, I think he’d have shied away from too much attention on his life, but I also think—I hope—he’d be glad that I didn’t try to make him into something he wasn’t. He was both a “remarkable human” and, as the codebreaker also claims, “an everyman,” and I tried to capture both of those truths.

DL: When I first heard you talk about this project, one of the hooks was about the scandalous nature of William’s journals. Was it always evident to you that William’s sexual exploits were a way to write about masculinity?

JBJ: I’m sure the book would have always moved in that direction, but it became inevitable that masculinity would be a central thread of the book because of the moment in which I started writing. I began work on the book in earnest in the lead up to the 2016 presidential election, when I was home on leave with our two small boys, and after the votes were tallied, I grew worried about what that outcome said about the nature of masculinity in America. What was this place I’d brought my kids into? I had one answer in the past—in the laid-bare life of my adulterous ancestor—and another apparent answer in the present—in the election of an open misogynist—so I felt compelled to chart possible futures of American masculinity. For me and my kids and everybody who comes after us.

DL: In the process of writing Cipher, you discovered white, Black, and multi-racial cousins, many of whom were also seeking answers about their genealogy. How has your family responded to reading and learning about William, who is also their ancestor? 

JBJ: Most of my family saw the diaries like I did initially: as a curiosity. They’re interesting in their strangeness, but because they were written two centuries ago, no one seems to feel any real connection to William Prestwood. I’m anxious to see if that shifts for anyone once they finish the book. I have heard from a number of distant relatives who’d stumbled across the essay I wrote for Oxford American, and now that the book is out, more far-off kin are emailing. Most of those interactions have been comparing notes on historical and genealogical research.  

The most wide-ranging and compelling conversations I’ve had have been with relatives connected to me by slavery. I write about some of this in the book, but as I encountered Black Americans with whom I share DNA, and we tried to pinpoint our 19^th-century shared ancestors, I found so many of my initial questions splintering into more complicated and revealing questions. I continue to think about those conversations. 

DL: Towards the end of Cipher, there’s a place where you write that the past rarely stays put, and that there is always more to uncover. How is that idea shaping your new work?

JBJ: I think place and all that it entails—including family history—will forever be a subject I’m exploring. I consider my first book a “memoir of place,” and Cipher is in many ways about how we inhabit spaces over time. I’m working on a novel now, and it’s nothing like Cipher or Bearwallow—it’s contemporary and leaning into conventions of detective fiction—but it’s still exploring unexpected connections to place and history and people. So, I suspect I’m simply tilling the same soil but with new tools and waiting to see what grows. 

That said, I’ve been writing some essays (in Garden & Gun and Our State so far) about our house. It was built in the 19^th-century, and while we didn’t know it when we moved in, it was built by my fifth great uncle. This discovery isn’t quite as scandalous as William’s diaries, but I do continue to turn up surprising bits of family history in the walls and deed books of our home, and I wonder if I’ll find a book in there somehow.

DL: You’ve described Cipher as an American story precisely because it exposes early America’s complicated history with slavery and racial discrimination. What do you hope William’s story—and even more so, the stories of the enslaved people who were a part of William’s life—can contribute to the discourse in a time when museums like the Smithsonian are being criticized by conservatives for focusing too much on the “negative aspects” of slavery?

JBJ: One of the wildest hypocrisies around us right now comes from people who are upset about the removal of Confederate statues while, in the same breath, dismissing any talk of slavery because “it happened so long ago.” While writing this book, I thought often of people I know and love who don’t consider the repercussions of slavery in the 21^st century—and don’t even want to engage in those discussions because “I never owned slaves.” In the book, I tried to provide lots of on-ramps to consider, if only for a moment, the ways that that history still reverberates all around us. 

Whenever a messy subject comes up these days, people tend to retreat to their camps, digging into the trenches out of some team loyalty more than any real engagement with the issue at hand. I wanted my approach to some of these ideas to discourage that partisan retreat because the issues come within a very particular story—they’re not abstract or “political.” 

I was talking to one of my cousins recently about the diaries and family history, and he asked, “So . . . we have this land because all we did was stay put?” We’ve been living on our particular plot of land for five generations—since the diarist’s grandson settled it—and none of us had to do anything to have it except be born. So, yes, our squatting there is, of course, part of the story. 

The other part of that story—the part that I hope my book teases out—is that what we have is something most Black Americans can’t. Even if no enslaved people worked our land, this place is still tied to a history of slavery because it is a kind of generational inheritance that most Black Americans can’t access. Once you start to notice these kinds of sustained effects of that “long ago history,” then you start to notice them everywhere, and so my hope is that no matter the political stripe, readers might begin to step into these historical considerations simply by stepping into my own wrestling with them.

DL: William’s journals inspired you to try journaling, but you didn’t continue. What was the difference between daily journaling and the tools you use as a nonfiction writer?

JBJ: I failed at journaling and diary keeping, in part, because I’m not disciplined or consistent enough. But I think another part of this failure is trickier for me to sort out. When I sit to write in a sustained way, I tend to have a public end in mind. The essay or project may fail or go in a drawer, but my intent is always to put it into the world.  E.B. White says, somewhat tongue-in-cheek, that the essayist is “sustained by the childish belief that everything he thinks about, everything that happens to him, is of general interest.” So . . . maybe my failure to successfully journal is ego. Unlike William, I want people to read my words. Another answer—one that’s less of a personal indictment—is that writing, and specifically literary nonfiction, is the art form I feel most pulled to, and so it’s not something that I’m also using to track my days or process my internal life. It’d be akin to a painter using canvas and brushes to make a grocery list.

I’ve become, despite my best intentions, a writer who needs large blocks of time to write. I have to sit in a space and get my bearings. And even then I move slowly, sentence by sentence. In other words, I’m not a daily writer. I am not currently living in a way that allows me to set aside chunks of time daily to write. Instead, I may block off half of a day once a week or stay up way too late to meet a deadline. I wish I could rush through an early draft or write some throwaway scenes in the car-rider line, but I am a word-by-word writer and so a successful few hours may only result in a few paragraphs. I don’t advise it.   

DL: You’ve lived with William for many years now: reading his journals, writing him letters, trying to understand the choices he made in his life. You’ve even described your relationship with William like being haunted. Now that Cipher is out in the world, has it released his hold on you, or do you think he will always occupy as much space in your consciousness?

JBJ: I suspect he’ll always be there, for better or worse. In a very literal, genetic sense, he is a part of me, but in the psychic sense, his life has shaped my perspective and that can’t be undone. I still see things and wonder, “What would William think about that?” His presence is a kind of welcomed haunting, and I think he’ll probably be floating around with me until I’ve passed on behind him. 

DL: Has your time exploring William’s life made you more or less hopeful in times like these?

JBJ: I think the oh-so frustrating answer is both. William’s life is bookended by the Revolutionary War and the Civil War, so I see him stepping into the early experiment of a country, and then I see that country arrive to a violent fracture. While I believe we’re living in unprecedented times politically, it has also been helpful to look at William’s life and recognize just how many terrible and unprecedented things were shaking out around him two hundred years ago. Strangely, there’s comfort in seeing that we’ve made it through some darkness. 

Of course, making it through wasn’t all butterflies and rainbows. Emancipation, for example, required uprisings and war, so that’s the other side of my both answer. As a country, we’ve survived horrific moments, so we can survive this one too, but William’s diaries also show that this survival may get worse before it gets better. I hope we right the ship sooner than later, but the pendulum swing isn’t always quick.