In short
Tocqueville Road Trip Episode 2 (“Against all obstacles”) explores what American democracy is “for” by visiting Sing Sing prison and meeting incarcerated students and their volunteer/education ecosystem. It links Tocqueville’s 1831 observations on penal reform, equality of conditions, and voluntary associations to today’s faith in self-improvement amid mass incarceration and prison violence.
Guests (named in transcript)
- Samson (incarcerated student in Sing Sing education program; gold-rim glasses, colorful scarf; discusses childhood losses, neighborhood limits, and “we made choices”).
- Jean France (incarcerated student; psychology degree via Hudson Link for Higher Education; describes Haitian/immigrant upbringing, feeling “not built for” certain opportunities, and using education to repair family relationships).
- Sean Peaker (guide/education program staff; formerly incarcerated; convicted of manslaughter at 16; served 17.5 years; later earned degrees and became Hudson Link director; mentors inside and supports reentry outside).
Key claims
- Americans downplay luck, increasing punitive attitudes; prisoners emphasize accountability.
- Prison education via volunteers/nonprofits can sharply reduce reoffending (Hudson Link: 2% vs 28% national).
- Voluntary associations (like Hudson Link) function as “schools of democracy.”
Notable examples
- Sing Sing classroom in the former electric-chair building (Old Sparky); “incarcerated individuals” terminology mandated by New York.
- Sean’s “Big Al” recruiting him into high school; red-pen tutoring and cap-and-gown graduation.
- Hudson Link’s post-release supports: housing, clothing, jobs, and ex-prisoner-refitted homes.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOTocqueville's Journey in America
1:25 to 7:37
Exploration of Tocqueville's observations on American society and prisons.
“More than a league wide and covered with sails, the great river runs north into a range of high blue mountains and disappears.”
Inside Sing Sing: A Personal Encounter
7:37 to 14:00
The host's first-hand experience and conversations in Sing Sing prison.
“The guard isn't the first person wary of mispronouncing my name.”
American Beliefs on Luck and Responsibility
14:00 to 15:20
Explore the American perspective on luck and personal accountability.
“Usually, the answer is a mix of the two in unquantifiable proportions.”
Jean France's Journey of Self-Discovery
15:20 to 20:05
Jean France shares his experiences growing up in poverty and his evolving understanding of his identity.
“The group I'm talking to are self-selecting.”
Education and Transformation
20:05 to 24:18
Learn how education has provided Jean France with new perspectives and opportunities.
“He's taking a psychology degree through a non-profit called Hudson Link for Higher Education.”
Lessons from Prison Life
24:18 to 26:08
Explore the insights gained from conversations with inmates about hope and the American experience.
“It's really not as hard as people make this sense.”
Sean Peeker's Story of Regret and Redemption
26:08 to 28:05
Sean Peeker reflects on his journey through crime, prison, and personal growth.
“Maybe our guide in Sing Sing can help enlighten me.”
Sean's Journey in Prison Education
28:05 to 33:30
Explore Sean's experience in prison and the unexpected support he found for education.
“Sean entered prison before he had finished high school.”
Building a Supportive Network
33:30 to 35:38
Learn how Sean's organization Hudson Link facilitates education and support for former prisoners.
“He got a bachelor's degree and a master's, and he had to do it all on a typewriter.”
Voluntary Associations and Democracy
35:38 to 39:42
Understand the role of voluntary associations in American democracy, as related to Sean's work.
“In an aristocratic society, when the people at the top wanted to get something done, they just gave the order.”
Show all 14 chapters
Reflections on Imprisonment and Society
39:42 to 42:01
Delve into the complexities of prison life and societal changes as observed by the host.
“That's about the same as the federal government spends on Medicaid.”
Tocqueville's Reflections on American Democracy
42:01 to 43:39
Explore Tocqueville's observations of America's democratic spirit in 2026.
“The America these men left when they were locked up was much less polarised too.”
Journey to the American Frontier
43:40 to 44:38
Follow Tocqueville's journey to observe democracy away from traditional hierarchies.
“Leaving the Hudson Valley, he and Beaumont turned west towards Buffalo, the gateway to the Great Lakes.”
Modern Challenges to Freedom of Expression
44:39 to 45:58
The quest for freedom of expression in contemporary America and its implications.
“This part of the journey is a little bit trickier to replicate.”
Transcript
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1:48More than a league wide and covered with sails, the great river runs north into a range of high blue mountains and disappears. Its banks are a scene of bustle and prosperity delightful to observe. And overhead is an unmarriable Sun whose rays, filtering through the humid atmosphere of the region, bathe everything they touch in a soft, transparent light.
2:19John Prideaux:Alexis de Tocqueville wrote those words in a letter to his father. He was perched in a tree at the top of a hill overlooking the Hudson Valley. The French aristocrat was a few weeks into his trip around America. After spending time with high society in New York, Tocqueville took a steamboat up the Hudson River. Our one aim since we've come here has been to comprehend the land we are exploring. We cannot accomplish that goal unless we disassemble society. And I dare say no man, whatever his social rank, is incapable of teaching us something.
3:03John Prideaux:Tocqueville's next stop was what was then America's biggest prison, Sing Sing. When he visited in 1831, it was just a few years old. He had been commissioned to write a report on the American penal system for the French government. That was the official reason for his trip, a great excuse to get funding for nine months studying a new democracy. At Sing Sing, he wanted to see something called the New York system. It was a novel approach that aimed to reform prisoners, not just punish them. It combined work with solitary confinement. The aim was to give prisoners time to reflect on their crimes, but also, through work, to give them purpose.
3:46John Prideaux:At the time, it was considered progressive. We are living here in the midst of 900 inmates, who, supervised by 22 guards, with no chains shackling them, no wall penning them in during the day, and no hope of saving money for a nest egg, worked from morning to night, like labourers on the job, in total silence. I remember seeing something of the sort among Trappist monks.
4:20John Prideaux:Prisons in France, then, were essentially dungeons. Not much had changed since the medieval period, and Tocqueville had a personal connection. His parents were jailed during the French Revolution. They narrowly escaped the guillotine, and his father's hair turned white in his early 20s from the stress. Given what the French Revolution had done to his parents, It's all the more surprising that Tocqueville was so enthusiastic about the American one. And yet, despite his background, Tocqueville wanted to show the people of France that there was no going back. America was the future. Even its prisons are offered an example to learn from.
5:07John Prideaux:Nobody has seen America as a beacon of penal reform for a long time. Relative to the population size, the country incarcerates six times more people than Canada. There are more Americans in prison than there are Americans in Hawaii, Maine or Alaska. And they can be violent places. Dozens of people are murdered every year while incarcerated. There are thousands of attacks on the guards. When I visited, New York state prisons were in turmoil. Earlier this month, an investigation was launched into the death of an inmate at Marcy Correctional Facility. Today, the Attorney General releasing body cam footage of an incident leading up to that man's death.
5:53John Prideaux:The system was reeling after guards killed an inmate on camera. The state government tabled a raft of measures, including more CCTV cameras, and increased inspections. Then guards went on strike, and many didn't return to their jobs. The National Guard had to be brought in to secure the prisons. Sing Sing was affected by the strike too. New York's prisons have a reputation for violence. But like in Tocqueville's day, Sing Sing still stands out for its reform programs. It's sometimes referred to as the Columbia of Prisons. University professors volunteer to come up and teach there. The train line from New York actually runs right through the place.
6:40John Prideaux:It's a much smoother ride than Tocqueville had. He called the roads deplorable and carriages infernal. When I arrive on the train from New York City, it's a bright, crisp winter's day. There's snow on the riverbanks and the edge of the Hudson is frozen solid. The cold air stings your nostrils. When Tocqueville was here, he was asking, how does a country built on the idea of liberty deprive people of their freedom? What happens to those who play the game of chance in America and lose? I'm going into Sing Sing with those questions in mind, and one of my own. Can people inside help explain what's gone wrong with faith in American democracy?
7:28John Prideaux:I'm John Priddo. From The Economist, this is my Tocqueville Road Trip, exploring democracy in America at 250. Episode 2, Against All Obstacles
7:58John Prideaux:The guard isn't the first person wary of mispronouncing my name. He's very welcoming, but I'm a little nervous. This is my first time inside a maximum security prison in America. Is it going to be like the Shawshank Redemption? These places can be terrifying. You got paper back there too?
8:23John Prideaux:There are strict controls on what we can take inside. No phones for a start.
8:32John Prideaux:Every piece of recording equipment has to be counted, down to the number of batteries. Two wireless microphones. Two mic covers.
8:47Ready to go, bro?
8:48John Prideaux:That done, we're led through corridors and heavy doors. The stairs are metal. Be careful. They're a little slippery. Our guide is Sean Peaker. He's taking us to meet some prisoners who are part of an education programme run by volunteers at Sing Sing. We're cutting through the bridge that goes over the train tracks. This is a portion of the cell block from 1825. I get a little thrill at that. Tocqueville would have seen these very walls. We're definitely getting a tour of the best bits of this prison, though. We're not going into the building where prisoners sleep. That may be because it's pretty grim there, or because of concerns about security.
9:28John Prideaux:Instead, Sean takes us to a building overlooking the place where Old Sparky once stood. That was the electric chair used to end hundreds of lives, including those of Julius and Ethel Rosenberg, the most famous Soviet spies in America. This building is now a classroom. There's a green chalkboard on the wall. Black paint is peeling off the floorboards. The window frames are made of cast iron. Hello, how are you doing? We miss anybody? Yeah, we're good. The prisoners are escorted by a guard into the classroom. All of the men wear the same standard-issue green trousers. Their top halves are their own to dress as they will, so long as they avoid certain colours.
10:10John Prideaux:Black is a no-no because it's good for escaping it. Sean and his colleagues shake everyone's hands, and we introduce ourselves. Could you please tell us who you guys are so that the men can be a little relaxed? The deal when talking to prisoners is that you don't ask about their crimes, and you don't actually call them prisoners or inmates. New York Democrats passed a law saying everyone, including the guards, should call them incarcerated individuals. Chairs are set out in a circle, and everyone begins taking their seats. One of the guys stands out in his gold-rimmed glasses and colourful scarf.
10:51John Prideaux:Samson, I'm sorry that you didn't get the memo that the camera wasn't coming.
10:58John Prideaux:Everyone's in a good mood. I still feel uneasy. Looking around, I don't know how many of these men have killed people. Judging by the length of their sentences, it's fair to assume most of them have. And so, I wonder where to begin the conversation. How can this group of hardened criminals help me understand why so many Americans have lost faith in their country, and why so many other people in the West have too. When you were growing up, did you think that you lived in a country where there was a lot of opportunity for you?
11:40John Prideaux:I realised young that choices make a lot of difference in what you're doing throughout life. My mum never graduated high school. My dad graduated high school, but they had kids, four kids by the time my mom was 22. We didn't have a lot of the things that other kids have. You know, other kids would have Doritos. We'd have that white pathmark, no frills bag. The men passed the microphone around the circle. Most of them are black. Many suffered terrible losses. Almost all of them had tough childhoods. My parents died before I was 12. I used to be embarrassed to tell people that too because they both died from AIDS-related illnesses due to their intra-hitting drug use, right?
12:24But from then, I was on my own. I never felt that when I was 6, 7, 8, 9, 10, my environment or my circumstances or my skin color limited me in any way. But that was kind of stripped of me when I was like 10, 11, and my friend got killed, and I know he was, he did everything right just like I was doing everything right. And then that's what kind of opened my eyes that it is kind of limited when you're from this neighborhood. So, my opportunities came at a young age, from going to the store for people for a dollar, to working for them, like transporting stuff and stuff like that or whatever. So I kind of got introduced to a different opportunity, which was drugs and that type of money.
13:10So my American dream was like an American dream of a drug dealer.
13:19John Prideaux:This kind of story is not unexpected from people who've wound up here. The American dream was distant. Drugs and crime seemed like a shortcut. But then someone says something that gives me pause. I made choices. We made choices. Unfortunately, that let us hear, right? but it's also we made choices that have us sitting in this room which are now so we're learning and that's America.
13:51John Prideaux:None of us have a reliable way to distinguish the things we do from the things that are done to us to distinguish between what happens because of good or bad luck and what happens because of our talent or effort? Usually, the answer is a mix of the two in unquantifiable proportions.
14:17John Prideaux:Compared with Europeans, Americans are much less likely to believe in luck. Even though American society is more unequal than Europe is, Americans are much more likely to say that people get what they deserve. This helps to explain lots of things about America. Tocqueville noticed the same thing. He reckoned Europeans were more fatalistic because they were descended from a feudal society where everyone had their place, whereas Americans were not. The tendency to downplay luck, whether it's good or bad, may also explain why American society is more punitive. If you don't believe in luck, then wrongdoing is a choice and should be punished accordingly.
15:01John Prideaux:As the men talk, the choices they made come up a lot, and a pattern starts to emerge. None of them shirk responsibility for what they've done. Someone at the prison association told me that you'll find more accountability in this place than you will on Wall Street. The group I'm talking to are self-selecting. No one's forcing them to be part of the education programmes. and they've chosen to come here today because they've got something to say about democracy in America to a foreign journalist. Still, they're smart, eloquent. They have presence. They all sit up straight and look you in the eye as they talk.
15:42John Prideaux:I'm slightly ashamed to say I didn't anticipate this.
15:52My family migrated from Haiti a year before I was born, right? So when I was raised here, I didn't realize how good we had it.
16:04John Prideaux:The microphone continues round the circle, and when it gets to a tall guy in a light brown sweatshirt, he starts telling the story of his life. Mind you, we was living in Flatbush. We wasn't living, you know what I'm saying? Like, it was, I think they call it black bottom poverty back then. Like, it was bad, but I didn't know it was bad because everybody was on the same economic level, so it seemed all right. This is Jean France. He has a shaved head and walks with a loping gait, like a big man who doesn't want you to notice how big he is.
16:39Every summer, my families always scrape up money to send me and my cousin to Haiti to spend the summer with my grandparents. So every time we went to Haiti, I realized how bad people really had it. You know what I mean? So I was able to see that we was doing good. As far as I was concerned, we was doing great. And everybody in Haiti looked at us like we was the jungles. Yeah, they was looking at us like Will and Arnold. Like they thought we was rich. I remember every summer when we left, we would have to leave everybody all our clothes, right? Whatever sneakers we was wearing, whatever clothes we had, we had to leave that to all the kids in the neighborhood because they didn't have what we had.
17:22When I get back to America, a lot of my friends were materialistic. Everybody had whatever the latest fashion trends was at the time. My family wasn't on that type of time. They was always on budget time because they know what it's like not to have. You know what I mean? So I looked like an immigrant because of the way my parents dressed me. And that was uncool. Okay, that actually made me ashamed of my heritage because I hate the fact that people could just tell by my clothing where I'm from. You know what I mean? You can't be American. You know what I mean? And that made me feel awake.
18:01John Prideaux:But still, John France didn't feel like he was poor, that some people were haves and some were have-nots. A trip to Manhattan with his mum when he was eight years old changed that. And I didn't really realise what half and half's not really was until one time we went to Macy's. I'm never going to forget this. And we was walking past a storefront that had a video camera facing the street. And it had a TV screen, TV monitor, where you could see yourself as you walked by. And I remember stopping my mother when I seen myself on the TV screen. I felt like, oh, I'm on TV. And I remember telling my mom, let's get that.
18:40And she shut it down immediately. She says, we can't afford that. And took my hand and we moved away. And I remember thinking like, damn, we can't, we can't, like, we just not built for this kind of stuff. Like, you know what I mean? They put this stuff out here for certain people. We're not that people.
19:03My mother worked constantly. like she had multiple jobs i couldn't tell you what kind of i'm where she worked at when we were kids because she was always working i stayed most of the times with aunts and uncles and i'm like life shouldn't be so rough like we shouldn't be struggling like this like i see what haiti look like so why we gotta work why we gotta work this hard and i'm not even getting the things i want you know what i mean i hate the fact that i'm wearing flea market sneakers and stuff like that Like, that was pissing me off. So I didn't really understand what this American dream was.
19:39I just wasn't aware of these opportunities. I wasn't aware of options because I didn't know what they were. Right? So it's like, so now that you know what these things are, it makes you like, damn. Like, first, you know, like my man say, like, you feel like, damn, I wasted so much time growing up as a kid because I was going left when I could have went right.
20:02John Prideaux:Like all the prisoners in this room, Jean France is a student. He's taking a psychology degree through a non-profit called Hudson Link for Higher Education. Because I pursued education as an adult, I was able to learn things about myself that I didn't know before. Like when I told you the story about walking in front of Macy's and wanting to purchase the video camera, and my mother said we couldn't attain it. it was through my pursuit of a behavioral science degree that I learned that had my mother was able to identify that okay we can't afford this what can we do to get that the juices turning inside my mind to figure out a way okay it's not impossible it is possible I just got to figure out a way for herself for this right so but she didn't know how to do that because she didn't know that we had options.
21:02John Prideaux:With a lot of time alone in a cell to think, coupled with a drive for self-improvement, Jean-Francis found that maybe Tocqueville's equality of conditions is alive and well after all. You know the saying, when you know better, you do better. One of my favourite quotes was by Fred Rogers from Mr Rogers' Neighbourhood. Fred Rogers was like Tocqueville, but for kids' TV. He was an avuncular figure full of teachable stories about the importance of social bonds. He said, there's no one you couldn't love once you heard their story.
21:41Right? And that always resonated with me because now when I look at people, I can empathise with them now. I don't care how bad a person may appear, how tough a person may look, a dude may be a bully, he may be whatever the case may be, you don't know his story. You don't know how he became what he is right now. And I'm saying that because on a personal level, same thing with me. Know what I mean? Like, I'm not saying this the way I want to say it. Say it the way you feel it. Like, okay, you know how you come up one way, right? Like when you're your mother's child, right? You know how she sees you when you coming up, right?
Read the full transcript
22:23And sometimes you might even see yourself like that as you coming up. but somewhere along that line, you stop seeing yourself like that. You want to start mimicking things that you think is acceptable, the things that you want to be like, because in your mind, in whatever twisted, warped sense of reality told you that this is what's cool, so you become something that you're not. Then you start living like that for years. until you have an epiphany and you realize this is not who I am. It's funny how, you know, they call it evolution, but it's like you start off with evolution and then somehow you devolve and then you have to evolve again.
23:14You know what I mean?
23:27John Prideaux:Jean-France says his education inside has not just provided opportunities for him, but also the people close to him. I'm able to repair fractured relationships in my own family because of the knowledge I have of psychology, which is amazing to me. I can't believe I'm actually able to help people in my family who are extremely stubborn see themselves through my eyes. You know what I mean? He's able to see his childhood differently now. He didn't have the support he needed growing up. Not because my family didn't care, only because they were just ignorant to that. Right? So, but now because of this education, now because I'm so aware of so many things, it's like, I could fake see the American dream.
24:19It's really not as hard as people make this sense.
24:26John Prideaux:I'd expected to find sitting in a room with a group of criminals and talking about the American dream to be uncomfortable. After all, what do they have to dream about? Instead, it's been oddly moving, like going to church when you need to, or seeing the stars on a clear night. Some rituals start with a candle, others with a deep breath. This one starts when the air shifts. The Sense of Calm collection from the Pura Calm partnership is three fragrances designed with sensory science to ground your space and quiet your mind. Sleep Story. A lavender drift into deep rest. Breathe Bubble. A mindful reset wrapped in white tea and cashmere.
25:13Soundscape. A fresh, clearing rush that restores your energy. Ground your space. Quiet your mind.
25:29John Prideaux:These men, who freely admit they occupy the lowest rung in society, are the most optimistic group of Americans I've encountered for a long time. They embody something Tocqueville noticed about America's lively faith in the perfectibility of man. He wrote that Americans are of the opinion that nothing is or ought to be permanent. What appears to them to be good today may be superseded by something better tomorrow. How is it that men in prison are the ones who can best explain what's special about America? Maybe our guide in Sing Sing can help enlighten me.
26:17I shot and killed my friend's dad when I was in the ninth grade.
26:22John Prideaux:Sean Peeker was convicted of manslaughter when he was 16 years old. He's now in his 50s. He's short, squat, and the skin by his eyes crinkles when he smiles, which he does a lot. He's been through the same program as some of the guys I met in Sing Sing, and now he's out the other side. His story starts like the others. Mom and dad were New York City cops, very worker bee community, and I was just kind of like flying under the radar. Because I wasn't doing well academically and I didn't play sports like my brothers, I wasn't a part of a lot of things. As a teenager, Sean didn't see much of a future for himself.
27:08John Prideaux:That's why he almost shrugs his shoulders at what happened next. When I got arrested at 16 and sentenced to 24 years in prison, it didn't seem like that big a deal. Which is so sad to say out loud. Going to prison instead of doing something amazing outside when you're not doing anything amazing outside. It was a weird, like, anticlimactic, well, I'll be here for the next two decades. Sean doesn't want to talk about the details of his crime. but he wells up when recalling the impact it had on his family. Crying easily is perhaps not something you expect from a former convict but it's something he's known for.
27:51They call them Sean moments and it's all right as long as they call it a Sean moment.
27:58John Prideaux:Sean moments are one result of a very American story.
28:05John Prideaux:Sean entered prison before he had finished high school. Life inside didn't get off to a great start. I was in and out of solitary confinement a bunch. And on my last trip, you get out of the box, you end up in the yard, in this notoriously shitty disciplinary jail. I'm just walking the yard. There's no part of what I'm thinking about except for I got decades to do here, potentially. The start of this prison sentence has not gone well. The days tick by. Sean walks the yard. Everyone is just walking in a big circle. And when somebody cuts that circle and goes across, it's because something's about to go down.
28:50Everything stops. Everyone's waiting to see what you're about to do. And Big Al is heading my way. And literally, Big Al is the biggest guy in the prison. And in my mind, I'm like, is he coming my way? you know like blend in you know which doesn't really work um so he comes up to me he says are you sean and you know there's this moment of like do i just lie and just like get out of no i've never heard of sean you know and i said yes he said i don't know if you heard but we have this uh youth program here and the teachers and the students come in and they'll spend the day with us. And the problem is that everyone on the crew is my age, which means we could be their parents.
29:38You're actually younger than a senior in high school. Like, I think it would be kind of crazy if you were actually coming in with us and you're younger than them. Maybe a little bit of an eye-opening experience. It seemed a little crazy that I would worry about going to school. I was sentenced to more time than I was on earth. In all honesty, envisioning surviving till the end of the week seemed like a lot, let alone for the next two decades. And I remember telling Al, like it was yesterday, yeah, with all due respect, I can't even help myself.
30:14John Prideaux:But this was a prison yard full of big men. You don't say no to the one called Big Al. Al says, oh, no, no, I'm not asking. It's Monday at 6. We'll see you there. Oh, oh, oh, God, great, Monday, I'll see you there. Al became one of several mentors to Sean while he was inside. Almost immediately, some of the older guys, the 26-year-olds, you know, came to my cell and they said, hey, we signed you up for high school. And I remember, like, it was yesterday being like, if there's any silver lining to going to prison for two decades, it's that I didn't have to fail high school. Because I escaped that failure by coming to prison.
30:56John Prideaux:Sean says he had struggled academically all his life. He thought he'd got out of having to pass exams. So the irony of having these three guys in the cell block say that we signed you up for high school and we will help you. I never heard that part of the equation before. As much trouble or as much struggling as I had academically, people would tell me what I'm not doing right, but nobody ever said, I'll sit with you and do it with you.
31:28John Prideaux:For the first time, Sean was getting support, even if he didn't want it. I argued that, you know, this is a big waste of time. But these older guys lived in better parts of the prison. They had key jobs like the warden's runner or the laundry or the kitchen. And they said, if you want to eat with us and hang out with us and live with us, you've got to get your high school diploma. It was worth it. I'm not going to say how many times I took that high school test. But when I did finally pass, the prison did an incredible job of caps and gowns. And the other prisoners were in the audience cheering.
32:05And it was a cake. And they made it a big deal. Sean credits his mentors with his success. There should have been 14 people up on the stage with me because every day after their mandatory prison jobs, they were out there with their red pens fixing my work and going over algebra and just these guys were relentless that I was going to get my high school diploma.
32:40John Prideaux:When I think of American maximum security prisons, I think of violence, boredom and terrible food. I do not think of people with red pens correcting each other's algebra homework. But Big Al and his friends had changed the course of Sean's life. And I remember on the day of the graduation, as the facility staff were getting me into my cap and gown, I said, oh, well, now I can work in the kitchen. And they said, well, you don't need your high school diploma to work in the kitchen. Oh my God, I was so fucking mad. They had completely lied to me. But it worked. And when I finished and I got that diploma, it was the first thing I'd completed in my life.
33:29John Prideaux:Sean was moved between nine different maximum security prisons, but he carried on studying throughout. He got a bachelor's degree and a master's, and he had to do it all on a typewriter. He was released after serving 17 and a half years. I had more time in prison than out. The world of technology had completely changed. I'd never seen a cell phone before except for on TV. But I did have a master's degree. Sean's education didn't stop there. He enrolled on another master's degree straight away. Then Hudson Link for Higher Education recruited him. It was a new organization bringing universities and prisons together.
34:15So the prisons get this chance to have these amazing programs that they don't pay for. The students have the chance to get this amazing college opportunity that they don't pay for. And we'll be in the middle to manage it and raise the money for it. It seemed really ambitious. but it was so many folks in the academic world and in this community that were willing to support it. Ten years later, he became the director. There are avenues that are being opened up, doors being created. Forget about being open, they're being created for formerly incarcerated men and women to change the world.
34:49John Prideaux:Hudson Lake also supports men who've recently been released. It provides clothes, a place to stay and even jobs. They have houses refitted by ex-prisoners where other ex-prisoners can stay as a toehold on the American dream. I feel like we're a college program that has snuck in all of these other avenues, and housing and construction and trucks and aftercare and the clothing boutique. It's all in this vehicle that we call college, when college has almost become the smallest thing that we do now. But it's the vehicle that we sneak it in with. In many countries, this work might be done by the government, but not in America.
35:31John Prideaux:Non-profits and volunteers provide the service. This was something which fascinated Tocqueville, the role played by voluntary associations in the young democracy.
35:46John Prideaux:In an aristocratic society, when the people at the top wanted to get something done, they just gave the order. In a democratic society, since people are equal, they need to band together to accomplish anything. Voluntary associations have other virtues, too. They're a buffer against an overmighty state. And groups of citizens organised around solving a problem serve as schools of democracy. Today, that still holds. Sean runs an association that Tocqueville would recognise. And that's something else that makes America stand out. Because in many countries, someone with Sean's past would not be in charge of the government agency tasked with prisoner education and rehabilitation.
36:34That is an unusual twist in this story that, yeah, I fucked up. I went to prison at 16. I'm going to be here for two decades, but I'm going to be friends with the Commissioner of Corrections. That's a little unusual.
36:45John Prideaux:But it's because Sean and his colleagues are who they are that it works. Part of the way we're able to do that is that we're also the only agency in the country that's run on staff by formerly incarcerated folks. So the same people that sat in those seats inside, they're coordinating the program outside. Across the country, 28 % of prisoners re-offend on their release. For Hudson Link, the figure is 2%. When Tocqueville visited, he was frustrated by a lack of data. He couldn't judge whether the reform system worked without knowing the re-offending rate. Today, it seems pretty clear that it can.
37:27John Prideaux:And yet, the provision of education in prisons is patchy in New York, and non-existent in some states. I just got back from a prison in Texas and there's just nothing there. There's just nothing there. So, thousands of people just walking around all day. And Sing Sing could be like that without Hudson Link. They also don't have a budget for this. They don't have a... Like, even if they want to do college, they couldn't. You know, we're raising millions of dollars a year with no state or federal help. In the time I've been reporting on America, I must have interviewed well over a thousand Americans.
38:11John Prideaux:Many of them have been important, successful or powerful. But I don't think I've talked to anyone more impressive than Sean.
38:21And all of a sudden, I'm now in charge of a college program in five prisons for men and women where I can say to a young guy just getting to the prison, you don't got to do it alone.
38:36John Prideaux:He's exactly the kind of American Tocqueville admired. A particular person conceives the thought of some undertaking. Should this undertaking have a direct relation to the well-being of society, the idea of addressing himself to the public authority to obtain its concurrence does not occur to him. He makes known his plan, offers to execute it, calls individual forces to the assistance of his and struggles hand-to-hand against all obstacles.
39:19John Prideaux:Tocqueville spent weeks in upstate New York. What he found there was a society that seemed to govern itself. Enterprising people, forming voluntary associations and solving problems they see with whatever means they have, just like Sean. Tocqueville thought that Americans did this better than Europeans, and I think that's still true. The flip side of wealth inequality in America is a lot of charitable giving, which the tax code encourages. Americans give away$600 billion a year. That's about the same as the federal government spends on Medicaid. Hudson Link, like thousands of similar organisations, relies on those donations.
40:02John Prideaux:Even within the prison, this urge to create voluntary associations, those little schools of democracy, exists. It's inspiring.
40:26John Prideaux:Once I'm back outside the prison gates, batteries counted again, I break my unspoken agreement with Sean. I can't resist googling what sent the men I spoke to up the river to Sing Sing. My instinct was right. Everyone I look up has killed someone. A couple of the stories are so horrifying they made tabloid news.
40:54John Prideaux:How can it be that I feel so inspired by these men?
41:01John Prideaux:More than anyone else I've met on this trip, they seem to understand what Togville thought was so special about America. You strip someone back, take everything away, including their freedom. Is that when clarity of thought begins? This might be part of the answer. The other part came to me as I reflected back on the intensity of the experience. These men were impressive in the literal sense of the word. They gave me their complete attention and spoke from the heart. I don't want to get carried away here. I know these are the men who have worked hardest to turn themselves around inside. I wasn't allowed to spend time with any others.
41:43John Prideaux:But I'm convinced there was more to it than that. They've had their connection to the world taken away. They've been isolated from the past decade plus of political and technological upheaval in America. Some of them have never held a smartphone. The America these men left when they were locked up was much less polarised too. The last time a majority of Americans still believed the country was on the right track was 2004. This prison is like a portal back to another version of America, which leaves me with more questions than ever about the state of democracy here in 2026.
42:29John Prideaux:After leaving Sing Sing, Tocqueville and his companion Beaumont carried on up the Hudson. They took a steamboat to Albany, the state capital. They were there on the 4th of July. New York's governor invited them to join the official parade. Veterans of George Washington's army rode in carriages ahead of them. It ended at a church where a young man read out the Declaration of Independence. It was a truly impressive spectacle. people sat plunged in silence until they heard the eloquent words of Congress recounting England's injustices and tyranny. At that a murmur of indignation and anger ran through the audience.
43:12When Congress pled the righteousness of its cause and expressed the noble resolve to free America or die fighting, it seemed that an electrical current was making hearts vibrate.
43:28John Prideaux:This was where Tocqueville first bore witness to Americans' attachment to their democracy as a kind of faith. It was a belief, in his words, deeply felt. Is that faith still there? After talking to the moneyed elite in New York and prisoners at Sing Sing, I needed to find someone in Middle America, someone who is experiencing American democracy in its most quintessential form, and Tocqueville can guide me there. Leaving the Hudson Valley, he and Beaumont turned west towards Buffalo, the gateway to the Great Lakes. A vessel was living on a two-day voyage across Lake Erie to Detroit. We could hardly miss a chance to see one of the frontier provinces separating the United States from the vast wilderness beyond.
44:26John Prideaux:At the frontier, that most American place, Tocqueville wanted to see the democratic experiment playing out away from social hierarchy and tradition. He would see that this is a land of opportunity for anyone with the drive to find it. This part of the journey is a little bit trickier to replicate. There's not exactly a vast wilderness north of Detroit. So I'm following him to a modern frontier, still in Michigan. But it's not a physical frontier. It's a technological one. You look at the site, you look at the scale of it, and you can't help but feel a sense of awe at what we're trying to accomplish.
45:12John Prideaux:In the rest of this series, I'll see the front line of the battle for freedom of expression in Boston. I can think of multiple occasions, even over the past few weeks, where I've been having a conversation with somebody and they're constantly turning their head over their shoulder, lowering their voice. I'll follow Tocqueville to the Ohio River and find a side of America he would have hated. Well, the Constitution's been thrown in a dumpster fire. It's not even followed. And on to the center of power, where I'll explore what the future of American democracy looks like. I've been blessed to have a very unique experience where not only do I have a relationship directly with the president, I have a relationship directly with every individual kid and their spouses.
45:58John Prideaux:The rest of the series will come out through June. To continue listening, you'll need to be a subscriber. Search Economist Podcasts Plus for our best offer.
46:12John Prideaux:Tocqueville Road Trip was made by Imogen Svotka, John Shields, Pete Norton, Claire Reid and me, with additional editing by Rosie Bloor and Sam Colbert. Wei Dong Lin is our sound designer, Darren Ung composed the music, and Nico Rofast voiced the extracts from Tocqueville. I'm John Priddo. This is The Economist. Some rituals start with a candle, others with a deep breath. This one starts when the air shifts. The Sense of Calm collection from the Pura Calm Partnership is three fragrances designed with sensory science to ground your space and quiet your mind. Sleep Story, a lavender drift into deep rest.
46:57Breathe Bubble, a mindful reset wrapped in white tea and cashmere. Soundscape, a fresh clearing rush that restores your energy. Ground your space, quiet your mind. Explore the Sense of Calm collection at pura.com slash calm.
From the publisher
Tocqueville saw America’s faith in its own democracy as a vital force. But these days the majority of Americans think the country is headed in the wrong direction. Can a group of maximum security prisoners in Sing Sing offer a vision of how to get back on track?
Guests and Hosts
- John Prideaux, The Economist’s US Editor
- Sean Pica, executive director of Hudson Link for Higher Education in Prison
- Jean Frantz, prisoner at Sing Sing Correctional Facility
Topics
- Alexis de Tocqueville’s views on voluntary associations
- Sing Sing prison education programme
- Prisoners’ views on the American dream
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