‘Greatest Escapes With Arturo Castro’ Episode 4: Dannemora Duo

Mental Floss is partnering with FilmNation and iHeartPodcasts to bring you the transcripts for Greatest Escapes, a podcast hosted by Arturo Castro about some of the wildest escape stories across history. In this episode, Joseph Gordon-Levitt (Flora and Son, Mr. Corman) and Arturo examine the troubling trends behind a modern day escape in Dannemora, New York. Read all the transcripts here.

Warning: This episode contains discussions of crimes that some might find upsetting.

Arturo Castro: This is Greatest Escapes, a show bringing you the wildest true escape stories of all time. Now in this episode, we’re telling the story of two escapees who had a true knack for smuggling tools into prison so they could cut their way out. I’m Arturo Castro, and I’m joined by a man whose talent on screen and behind the camera has been completely undeniable for decades, one of my favorite co-stars of all time, please welcome: Joseph Gordon-Levitt.

It’s Joseph Gordon Levitt! “Brah brah brow!”

[Airhorn sound]

Joseph Gordon Levitt: Hey man.

Arturo: Hey.

Joe: Thanks for having me.

Arturo: Of course! Thanks for being here. And Joe, I gotta tell you, you know, and our audience—you know this, but you are one of the kindest people I’ve ever worked with. And I mean that very sincerely.

Joe: I feel the same way about you, man.

Arturo: And I’ll tell you what it is, man, that you just like—no matter who it is on set that has a question, you always stop and make time to answer it no matter how small it could be. Like, you know.

Joe: Because I just love hearing myself answer questions, that’s why.

Arturo: Yeah, yeah, yeah, yeah. If there’s somebody recording it and a, and a—and an artist sort of drawing, you do it at all times, which is weird, but I’ll give you an example. If somebody comes over and they’re like, “Hey, so yeah, I think I’m just gonna make those curtains blue,” and you’re like, “uh, wait, wait. Stop the roll.”

Joe: No, no.

Arturo: Hmm. OK. So I wanted to ask you, even though it’s kind of a—a hard question to ask while being modest, but, you know, being in films for as long as you’ve been and still, um, being such a well adjusted human being, what, um—what do you attribute that to? How you’ve sort of kept your head straight all these years?

Joe: That’s, I mean, so flattering that you would ask me that. Um, I mean, it’s a pretty simple answer. I think I got real lucky with the parents I got and, you know, that’s, that’s not my doing that—we all just roll dice and get who we get. And my parents were never very enchanted with all of the poisonous accoutrement that can come along with show business. I’ve, you know, I’ve been working in—acting in stuff since I was 6 years old and my parents always just saw that I loved doing it. But anytime I didn’t want to do it, if I, like, didn’t feel like going on an audition that day or something, my mom would always say, and very sincerely, “look, you really don’t have to do this. We’ll, you know, we’ll be so in love with you and proud of you no matter what you do.”

Arturo: Wow.

Joe:  “You did commit to this thing today–”

Arturo: Right.

Joe:  “–and it’s important that you honor your commitment. So let’s go today, but if you—after that, if you don’t want to do this, you, you never have to do this.”

Arturo: Wow.

Joe:  And, um, I think it’s—it’s more common that people feel pressure to do it.

Arturo: Of course.

Joe: And, and that can be the beginning of the—I don’t know.

Arturo: Yes, “of the end.” Say it.

Joe: [Laughs]

Joe’s Escape

Arturo: Let me ask you something. What do you consider to be your greatest escape?

Joe: Yeah, well, I, I—honestly, I think what we did escaping the pandemic to New Zealand, and I feel half bad, you know, saying this ’cause it was such a privilege to get to do it, but that was an incredible escape.

Arturo: So amazing.

Joe: And just to tell the brief version of the story, you know, we were shooting this show, Mr. Corman, that I’d been, you know, trying to put together for years—it’s my baby. We’re three weeks into the shoot in March of 2020 when—when the whole world shut down. We have to stop along with everybody else and we were trying to get the production back up. Everyone was running around trying to figure out how to shoot during the pandemic.

Arturo: Right.

Joe: And the intrepid producers over at A24 called me and said, “would you ever consider spending a lot of time in New Zealand?” And I was—I mean, I—I felt like I won the lottery.

Arturo: Yeah.

Joe:  I had been fan—I literally, not exaggerating, my wife and I had been fantasizing. We had been staying up at night looking at Google Maps street view of New Zealand–

Arturo: Wow

Joe: –picking where we wanted to be, just because it sounded like such a dream to be out of the pandemic. And, you know, there was no Covid there at the time. And, and then we got to go, and I remember—and [I] got to bring my family and we spent [a] time there and—a long time—and, and I remember when we got there, my older boy who at the time was I think 5, we got off the plane in the the airport in Wellington and no one was wearing masks. And we got off and we took off our masks and my boy goes, “we’re out of the pandemic!” And I was like, yep, that’s exactly what happens. Leave it to a 5 year old.

Arturo: But it was an escape, right? It was just like, we were able to—I remember I would post stories or I send my friends videos of like just shopping at a grocery store without a mask. And it was like, the biggest flex in the world.

OK, so are we ready to get into this? Do you want to hear some crazy escape?

Joe: I wanna hear this story. I—I love storytelling, so I can’t wait.

Arturo: I’m gonna hit ya.

CHAPTER 1: Two Bros Diverge

Arturo: It’s the summer of 2015, and we begin in a remote hunting cabin in upstate New York. The rooms are dark, quiet, musty. The cabin is empty. Footsteps approach. Crunch crunch. I’m not gonna do my own sound effects … Two men come to the door. They try the handle. Their silhouettes loom in the windows. They force their way inside. Yes, it’s a break in. The men are looking pretty rough. They’ve been trekking through the woods near the Canadian border, living off the land, and carrying their supplies in a battered guitar case.

Joe: A guitar case?

Arturo: A guitar case.

Joe: So they didn’t—they didn’t mean to go living in the wilderness as they’re carrying a guitar case.

Arturo: Well, no, they didn’t. This wasn’t part of their plan. They have ragged name tags. They’re still sewn into their clothing. It’s—they’re called David and Richard.

Joe: Name tags? What, like TGI—TGIF waiters or something? What?

Arturo: Yes, yes. They both work—they work at Applebee’s, and this is just some crazy turn of events. They are now in the woods. So they’re in this crusty cabin in the woods, and it’s a gold mine. They rummaged through the cabinets and dressers. Do you have any guess what they’re gonna find there, Joe?

Joe: I mean, food, water, I don’t know. Like, Nintendo?

Arturo: A TGI Friday’s store! They found a full-on—so they open up a fully stocked pantry and begin to feast, but even better, they find a bottle of moonshine and a propane heater, and they also find plenty of choice weed. So while one of them sleeps—sweeps up the glass, the other one grabs a moonshine, rolls a joints, and settles on the couch. We get a glare from the sweeping guy and he takes a long–

Joe: Mixing marijuana and alcohol. Not my favorite.

Arturo: Not a favorite thing to do. It always seems like a good idea. You know, when I was younger, like, you’re drunk at somebody’s like “you want to hit this?” and suddenly I’m like, “yeah.”

Joe: Just pick one. What kind of evening do you want to have? Pick one.

Arturo: So suddenly, I’m in the couch, in brain jail, being like, “oh man, three years ago I was kind of rude to that barista, I should call them.” Um, so this is when David and Richard’s great escape started to go sideways. They were two murderers on the run after an epic prison escape …

Joe: Jesus!

Arturo: … and the law was hot on their heels.

Joe: Oh damn.

CHAPTER 2: Right Where You Belong

Arturo: So Joe, let’s meet these two shady characters, OK?

Joe: OK.

Arturo: Um, we established they’re not actually from TGI Fridays, uh…

Joe: No, they’re prison name tags afterall.

Arturo: Uh, exactly. So these guys were worse than shady. These two guys were cold-blooded killers. And so we’re gonna start with David Sweat.

Joe: Wow.

Arturo: Yeah. So he was born in 1980 and he grew up in a little town of Deposit, New York. Incidentally, it’s not known for their deposits. They were all cash in hand. Um—but that was such a stupid joke, but I had to get it in there. So by the time he was 18, David had already had a long rap sheet, a list that included violent attacks and burglaries and car crashes to his name.

Joe: What kind of parents did he have?

Arturo: He did not have great parents. They all, yes. None of …

Joe: I feel bad for David.

Arturo: They all believed in name tags. That wasn’t even a prison thing. They just like—it was just a thing he picked up from youth. So once while he was in prison, a guard found him making a list of future crimes that he hoped to commit one day.

Joe: Whoa!

Arturo: Dude, you gotta admire the f***ing audacity of this insane vision board.

Joe: Is he writing down just like, the actual offenses? “I want to perform armed robbery—check. I want to perform arson—check.” Or is he like describing stories of like, things he wants?

Arturo: No, he’s like, “I want to commit each and every one of these before my time is done.” So!

Joe: Oh, he’s ill. He’s—he’s sick. He’s mentally ill.

Arturo: He’s a sick man. But when he first got out on parole, David started living out of—out of a camper in the woods in upstate New York. He gathered some friends, uh, like-minded friends, you could say, and they started boosting cars from the parking lots of nearby towns. 

Now, David—sorry, let me ask you this. Let me go back to this for a second. Do you believe that some people, even if they’re not mentally ill, or there’s not something inherently wrong with them, do you think there’s just some people that are born cruel or they’re raised cruel?

Joe: I mean, cruel has the value judgment. I—I definitely think [there] are people who are born ill, and I mean, I’m sorry to get all serious here. We’re trying to have a fun time telling an escape story, but like, for sure our world, especially our country, does not do a good job of taking care of mentally ill people.

Arturo: A hundred percent.

Joe: And the fact that someone who’s clearly, uh, mentally ill has ended up in prison, that’s probably not the right place for him. That’s not gonna help him, and–

Arturo: And to your point, through, through—throughout these stories that we’ve been telling, a lot of them are prison escapes and nobody, not [one person] in any of these stories gets reformed by going to the prison system.

Joe: Exactly. It’s supposed to be rehabilitation. Well, it’s—it’s worth noting, you know, in—uh, sorry to get all geeky about this. This is something I’m quite interested in.

Arturo: Sure.

Joe: Uh, there’s a lot of prisons that—they actually are private for-profit companies, so it’s in their interests that they have more prisoners.

Arturo: A hundred percent.

Joe: And so, what—what incentive do they have to make sure that their prisoners rehabilitate and get out and go lead more healthy, positive lives? They don’t—they have the incentive to bring them back. Like any good business, you want your customers to come back–

Arturo: A hundred percent.

Joe: –and I do think it’s—it speaks to the kind of larger values and understanding, and this goes back to the kind of meritocracy myth that we were talking about a minute ago when you asked like, “Hey, well, how, how did you end up so lucky to be, you know, a, a happy person?” And I—I think so much of it comes down to luck, whether that’s who your parents are or just the—the physiology in your brain are, are … are all the cylinders firing right? Or are some of those cylinders firing in a way that drive you as a young person to, to think about crime and want to do that. I—I definitely think that that’s luck.

Arturo: Yeah.

Joe: And, you know, the, the—there’s a saying, I—I forget the exact wording of it, but like, the measure of a, of a good, kind society is how well you treat the unlucky people.

Arturo: Joe, because we’re spending too much money spying on our own citizens, buddy. Like, you know, that gets expensive. People need to know who I’m f***ing texting, man. You know?

Joe: Mm.

Arturo: Um, so when he was with this like-minded, with like-minded people, uh, David bragged to others about the police scanner that he used to avoid cops, and he said that if they ever came at him, he would blow them away. So in 2002, on the 4th of July, David Sweat and two accomplices ran their truck through the back wall of a fireworks and gun shop. They ran through the store and they loaded up a duffle bag with guns—and also fireworks and guns in the same shop. Is there anything more American than a flagship store of everything that goes, boom, you know? [radio ad voice] “You like guns? You like explosions? Why spend any time anywhere else?”

Joe: “When you’re having fun? There are fireworks when it gets serious. We have weapons.”

Arturo: “And when you don’t know, which—bring both.” 

Uh, which is kind of incidentally the—the tagline for my quinceñera. 

So with their loot, David raced to a tiny park three miles away where they were moving the guns from to a second car. That’s when a local sheriff’s deputy pulled up in his cruiser and had him in the headlights. Now the deputy got out of his car to confront the man, but David Sweat just started shooting, man, and he and the other robbers shot the deputy 15 times, stole his gun, and even—this is f***ing rough. They ran him over with their getaway car.

Joe: So sad.

Arturo: Also, coldblooded premeditated murder. But, and again, not to go on another tangent of this, but you know, it’s—I’m, I’m sure for the family of this deputy, it’s hard to understand this, you know what I’m saying, it’s hard to have any sympathy for somebody that just killed your f***ing husband. It’s crazy times.

Joe: Of course, of course. But—but that’s just it. It’s bad for the police too. Like, why the first government intervention of like, trying to handle this very sick person should not be a sheriff’s deputy.

Arturo: A hundred percent.

Joe: The—there should have been a mental health professional talking to this kid a decade prior– 

Arturo: Right.

Joe: –so that he doesn’t kill the sheriff’s deputy. That’s exactly the problem.

Arturo: Exactly. So then they made it their escape. But David could not stop bragging, and so within a week, David’s—it always f***ing happens with criminal, uh, with the criminals that we learn about here.

Joe: What was he bragging about? He’s like, “they’re gonna f***ing talk about me on a podcast one day.”

Arturo: That’s right. Uh, so within a week, David’s girlfriend told the police, and when they caught him, David pled guilty to the murder in order to avoid the death penalty. He received a life sentence without parole. Now, they sent him to Clinton Correctional Facility in upstate New York, and that’s where he would meet our next escapee, Richard Matt. His story’s a lot like David’s. You know, he was another troubled kid who didn’t get the help he needed when he was a kid. He actually ran away from a foster home by stealing a horse and riding off.

Joe: Wow!

Arturo: At the age of 14, he even tried to steal a houseboat. Man, you gotta give this guy credit for like, niche getaway vehicles.

Joe: Yeah.

Arturo: He was also well known for a penny farthing escape, you know? Have you, have you ever owned a unicycle or a—a ridden a penny farthing?

Joe: My wife can ride a unicycle. I’ve never owned one personally, and I’ve tried to ride it. It’s very difficult.

Arturo: I’m sure it is. I don’t think I could ride—also ride one fast enough to like, get away. I would love to see that. That should be our new reality show. 

So Richard’s crimes only got worse from there, right? Felony, felony weapon charges, felony assault, and plenty of misdemeanor harassment charges. It’s like he just couldn’t meet somebody without attacking them, you know? So when he was caught, he often escaped heavy charges by pleading guilty to lesser crimes. 

What’s the most trouble you ever got into as a kid?

Joe: Uh, I—I remember shoplifting a greeting card once at the mall cause there was a picture on the front that looked like my dog and I wanted to show it to my mom and dad–

Arturo: Adorable.

Joe: –and I—but I also probably, I think I had probably enough money to buy the thing, but I was tickled by the idea of, you know, stealing it. And, uh, what do you know? I didn’t get caught like, uh, you know, white suburban Jewish kid in a, in a mall. Like no one punished me or sent me to foster care for, uh, shoplifting.

Arturo: Well, actually funny you should mention that because we have the shop owner here with us today. Come on out.

Joe: Oh, I’m sorry!

Arturo: We found him. We f***ing found him, you guys.

Joe: It’s still on the refrigerator at my parents’ house. I can give it back to you.

Arturo: No, no, no, no. He’s, he doesn’t wanna speak right now, but he is very mighty miffed. 

So the neglect was obvious though, you know, with—with Richard’s life. He made his first prison break the easy way. A guard left his prison cell open and he just kind of f***ing walked out, you know? I didn’t know that that’s sh*t you could do. He scaled this 9 foot–

Joe: Wait, so was the guard in on it?

Arturo: No, no, no. He was just neglectful. You know? We also have him here. He’s—he’s just keeps giving me excuses.

So this guy scaled the 9 foot brick wall and slashed up his arms on the barbed wire in the process, he jumped the freight train to make his escape, but he didn’t go far, though. It only took him four days for police to catch up with him at his brother’s apartment. So you know, he’s not the brightest dude at hiding, but he’s good at the first part of escape—but he lacks a little follow through, which is what we’ll see later on in the story. So every time he got outta prison, Richard committed horrible assaults. It was a pretty vicious cycle, and this part is nuts, OK? Once while he was in prison awaiting trial, he struck a deal with another inmate to kill the dude’swife. The dude paid for Richard’s bail, but once Richard got out, he turned the tables and told the authorities about the plot.

Joe: OK.

Arturo:  But wait, it gets—it gets crazier. Wasn’t this guy, uh—married to the heir of the Warner Bros. fortune, overlords?

Carl: That is correct.

Joe: Wait, wait, wait. The guy that was hiring Richard to kill his wife while in prison, that guy, the wife that he wanted to kill, was the great-granddaughter of the actual Warner Brothers.

Arturo: Yeah, yeah. That’s right. She was an heiress of the Warner Brothers family. Can you believe?

Joe: Oh, wow.

Arturo: So he got out because he ratted on this guy, but his next crime was the only one that would finally get him locked in maximum security. Now it started when he took a job with a business dealing with near—get this—nearly expired meat. So they would buy it cheap and they were reselling it to new customers.

Joe: Oy, what?

Arturo: Oh. Yeah. So it’s a thing

Joe: Nearly? N.E.M.? Nearly expired meat…

Arturo: Nearly, yeah. 

Joe: I’m in the N.E.M. Space.

Arturo: It was a keto, it was the old keto version. So have you ever had any sketchy jobs?

Joe: I mean, I’m an actor, so it is kind of a sketchy job.

Arturo: I hear you. Um, so Richard made his expired meat job even more sketchy. He started stealing the meat, smuggling over the border into Canada for cash that he would then take to strip clubs, right? So who’s buying all this f***ing expired meat, by the way. I don’t want to know. So after–

Joe: Not the strippers.

Arturo: No, yeah, not the strippers. I hope. After only a few weeks, the boss caught him and fired Richard. Now, unfortunately for the boss, Richard had overheard him make a comment one time about 100 grand that he had buried in the basement. So Richard thought it was real and he wanted that money. So he got a friend and the two of them rolled up on the meat dealer at his house. They beat him up, they stuffed him into the trunk of Richard’s car and they drove around for hours stopping to interrogate and beat the guy. They never learned anything from him so Richard eventually just killed him, but here’s the most gruesome part–

Joe: Whoa. Really?

Arturo: Yeah, here’s the most gruesome part: Richard cut him up into pieces and dumped him in a river.

Joe: Oh my goodness.

Arturo: Yeah … So he went to Mexico, but like David Sweat, he just couldn’t keep quiet. He went berserk and killed another man in a bar.

Joe: Jeez.

Arturo: Richard did nine years in a Mexican prison before he got shipped back to the United States. Also how bad do you have to be for the Mexican jails to be like, “no, cabrón. You know what? I, you, we can’t have—no, no, you can have him. This is too icky for us. No, like I don’t like the vibe. I don’t like–” You know what I’m saying? Also speak–

Joe: “Don’t give him to us! Send them back down there!”

Arturo: “No. We had him. No, this guy just keeps pissing on us. I don’t like it. He keeps selling us expired meat. Where does he get from? Where does he get, you know–”

Joe: “You’re gonna take him and you’re gonna pay for him.”

Arturo: “Oh goddamn it. Fine.” Uh, speaking of Mexico, our audience might not know that you speak Spanish, Joe.

Joe: Yo entiendo mas que puedo hablar, no es muy bueno en español.

Arturo: Uh, he just insulted me and my whole family, for our non-Spanish speakers. And I do take offense—wait, sorry, uh, just quickly: Spanish, French?

Joe: French should be—French better than Spanish.

Arturo: OK. Spanish, French, and English.

Joe: Yeah, yeah.

Arturo: That’s impressive, man. When are we starting with Dutch? You and I just like, just throwing it out there. On the weekends, we can learn it in a year, will be great for–

Joe: Let’s do Chinese.

Arturo: That, oh my God, I would love to.

Joe: Why, why not?

Arturo: I would love to [learn] Japanese that I would really, really love.

Joe: Yeah.

Arturo: Back in the States, uh—they have Richard back with him. And Richard finally stood trial for murdering the meat boss. And this time they really tried not to let him escape. So they put him in a stun belt and even posted snipers on the roof of the courthouse.

Joe: A what?

Arturo: A stun belt?

Joe: What is that?

Arturo: I’m guessing it’s like a stun collar for dogs, but like you just, you just have it around your body—torso?

Joe: You mean like what—while he was in court or while he was—he was sitting there in a, in a belt and someone’s got a button when they can shock him?

Arturo: I’m thinking while they’re transporting, is my guess, but let me get my overlords on this. What do we mean by a stun belt, you guys?

Carl: Joe is correct.

Arturo: He was sitting in the court and somebody has a button.

Carl: Yes.

Arturo: F***!

Joe: Whoa, that’s … wow.

Arturo: OK. Uh, well.

Joe: Sounds, sounds like a, a good, fair trial if you’re, if–

Arturo: So at the trial—but he was easily convicted and they sent him to Clinton Correctional Facility and that’s where he met David. And the two of them started planning their great escape.

CHAPTER 3: Honor Block

Arturo: Now we’re in 2008, when David Sweat and Richard Matt are serving their respective prison sentences in Clinton Correctional Facility. So David had been there for eight years and Richard was a new arrival. But Richard even came with a new nickname: Hacksaw. 

I wanna think that David—yeah—I want to think that David was extremely jealous of what a hard ass nickname that he wanted—he wanted to make up one up for himself, but had never caught on, you know, like, “Call me Lion Eater.” “No, sorry dude, [you’re] just kind of, David.”

Joe: Hacksaw and David, David and Hacksaw. That’s our show.

Arturo: That’s right. That’s it. That’s it. He just never f***ing—he’s like, “We can call you Sweat.” Uh—you ever have a nickname, Joe?

Joe: I was doing a movie about soldiers and we all were doing a simulated bootcamp, which is about the—you know, that’s as hard ass as I get, a simulated bootcamp. It was like Crazy Ass Jan ’cuz he is—is sort of a crazy person. Smoking Ass Ryan ’cuz he smokes a lot. And, um, it was—uh, they called me “Regular Joe” because they were all—they were all too prissy to sh*t in the outhouse, and they wouldn’t sh*t. And I—I don’t care. Like I’ll go take sh*t—I’m not gonna not take a sh*t every day like …

Arturo: When Joe has to go, we just, you know, on set, I noticed this. We just have to look away. We just—if Joe has to go, this man will not walk two feet. He will just f***ing drop trow.

Joe: Stay regular, man. Eat a lot of vegetables. I’m gonna go sh*t in the outhouse. Come on. So I was Regular Joe.

Arturo: There you go.

Joe: And that name kind of stuck. Some people still call me Regular Joe.

Arturo: That’s a good one. Um, so let me tell you about the—let me tell you about this prison that they were in, right? So as—and I wanna check in with you. This is—how are you feeling? This is—it’s a hard story to hear, isn’t it?

Joe: It is hard for me. I, uh, I have to admit, I—I have a hard time enjoying the horrendous misfortunes of these, um, terribly tragically ill people and the—the pain they caused. But I—I’ve run the, the moral calculation in my head as we were doing this. And at that—that’s exactly where I netted out. It was like, OK, well if we can make a podcast where we’re, yes, we’re telling a story that’s crazy to hear, but we’re also actually breaking it down and trying to understand what are the larger problems in our world that are—that are leading to these things, that sounds like a fair way in to have some important conversations. So I’m—I’m down, I’m in full support to be going through this story and—and having this conversation.

Arturo: Awesome, man, thank you. Yeah, I agree. And I think it helps to do it with some context, right? So, let’s go back a little bit and get into the history of the prison they were in. So the prison was called Clinton Correctional Facility and was originally built by labor gangs of prisoners in the 1800s. The cold winters gave the prison its nickname: Little Siberia.

Joe: Labor gangs. Wow. Sorry. I just—labor gangs. It, it’s—it’s an important thing to note the, the American prison system is—there’s, there’s not even a dotted line between the American prison system and the American slavery industry from back in the day.

Arturo: Not even a dotted line.

Joe: Like, it’s not even a—it’s a solid line. It’s not even a very long line. It was like, as soon as slavery was outlawed in whatever it was, 1865, very, very shortly thereafter, they started figuring out, OK, well then how are we going to get all this work done? And prisoners, uh, was exactly one of the biggest answers and it’s still happening today.

Arturo: And for our listeners, if you wanna hear more about it, Ava DuVernay did a great documentary, The 13th, which you can find on Netflix which was incredibly powerful.

Joe: Yeah.

Arturo: Um, so, you know, imagine the conditions of any place when it gets compared to a f***ing Soviet gulag, like Little Siberia, too. You know what I’m saying? That’s when you’re really f***ing up. So the guard towers and the 60-foot concrete walls dominate the surrounding streets. Now in 2008, the people locked up there were put to work in an assembling office. They were making furniture, clothes, license plates, and road signs in an industrial building inside the prison walls. It’s like a f***ed up Etsy shop. You know what I’m saying? Like it’s just, like, wrong.

Joe: Yeah.

Arturo: So most people in this—and this is another thing, right? Most people in the surrounding town, called Dannemora, worked jobs in the prison. They were guards. Clerks, cooks, and supervisors for the prison laborers. For instance, take Tilly—and she’s gonna be essential to our story. She and her husband both worked in the prison and Tilly had been a supervisor since 2008. She ran the show in the tailoring shop, and that’s where she met David and Richard.

So, there are conflicting stories about what happened in the tailor shop, including whether the sexual acts were consensual. Even Tilly’s own account has changed over time—what she told state investigators differs from the accounts that she’s given to the press. It’s possible that Tilly was herself the victim of sexual violence and coercion and we just want to make it clear for our listener, there are multiple sides to this story and the facts are not 100 percent clear.

At first, maybe it seemed like there wasn’t much to worry about. After all, David and Richard lived in Cell Block A, which was known as the honor block. So inside Clinton Correctional, Richard and David had taken up painting and built themselves a good reputation. ’Cause if history has taught us anything, it’s that people who take a painting class never do anything wrong. Ever. Ever.

So in the tailor shop where they worked, David had also become really good at sewing and was even made shop instructor. Now, other workers started noticing that Tilly had made friends with David. She started bringing him contraband treats, and at first it was things like homemade brownies or cookies. But once, Tilly even brought him a Big Mac from a McDonald’s … that was almost an hour away from prison.

Joe: Wow.

Arturo: That is f***ing commitment, dude. My girlfriend and I, like, argue about who’s gonna shut the lights out like four feet away from our bed.

Joe: Yeah. OK. I was gonna say, hour-long Big Mac run. That’s not just buddies.

Arturo: That’s not friendship. No, no, no, no. And so eventually the violations were too obvious, you know, an anonymous letter to the prison administrators got David kicked out of the tailoring shop, and that’s when Tilly got close to David’s prison friend Richard—like very, very close.

Joe: OK.

Arturo: As we noted earlier, there are some differing accounts here about whether or not their relationship became sexual. By the spring of 2015, the state investigation reports that it was Tilly and Richard who were going to the empty room for sex. Tilly would also give Richard sexual notes to pass along to David, including nude photos of herself. Later, in at least one interview, Tilly said that she was worried about her safety and her husband’s life, but we’ll come back to that, OK?

Joe: OK, so she’s—she’s married during this?

Arturo: She’s married to—to a guy that works at the prison.

Joe: Wow.

Arturo: So, because despite all of this special treatment inside the prison, Richard and David were determined to get out.

CHAPTER 4: Hamburger Helper

Arturo: So listen, once David and Richard had Tilly tangled up in the most bizarre throuple ever, they had to plan to use her as a means for escape. Richard and Tilly started to trade. At first it was just small things, you know, paint brushes for their art, stuff like that. But then it started to get a little more elaborate—he said he needed some glasses with built-in flashlights, cause it would help him paint at night. He then said he needed some hacksaw blades. What do you think she thought he needed this for?

Joe: He was just jealous of the nickname, he needed to have his own hacksaw.

Arturo: David’s like “I wanna be Hacksaw, too.” You know, “I’m tired of being Sweaty Sweat. I’m Sweaty Dave.” So Tilly brought in the blades secretly and stashed them at Richard’s workstation in the tailoring shop. Then to get them out of his cell, Richard taped them to his body and on the walk—and this is important—on the walk back to the tailoring shop, the guard let him go around the metal detector, right? So this was honor block, after all—what reason did he have to be suspicious of Richard? But this just seems like gross neglect or he was in on it, right?

Joe: Yeah. Why? I mean, if there’s a metal detector there, what’s the point.

Arturo: Why don’t you just go f***ing through it? Yeah.

So once he was back in his cell, Richard passed half of the blades to David next door, and the two men went to work. They started to slowly cut the steel walls of their cells. They would wait until the evening, when other inmates from other blocks were allowed to use the common recreation areas. Now, Richard and David would hang back and they all say—they always said they were painting or something like that. So night by night, inch by inch, the men cut holes into the back walls. They covered the holes with their own paintings and that’s when the plan really began.

Joe: Hold on. They’re cutting a wall. They’re, they’re cutting a hole in a wall. The wall is made of—how do you … how do you cut a hole in a wall, even if you have a hacksaw? How do you even do that?

Arturo: With a lot of patience, Joe.

Joe: Yeah, I guess. Jeez.

Arturo: No, no, no. Uh oh. Overlords, was this a—well, they were hacking at the concrete? Was it …

Joe: Was it the bars? No, they couldn’t do it at the bars. That’d be visible, right?

Arturo: It wasn’t the bars.

Carl: Yes, their cell walls were made of steel.

Arturo: Wow. Interesting.

Joe: And you can do that with a hacksaw?

Carl: With a hacksaw blade, yes.

Ben: And to you’re right, patience. Yes, absolutely.

Arturo: Patience, and—yeah.

Joe: Ok. So they just—this is a long-term project.

Arturo: You know, a lot of—when you hear about a lot of these escape stories, there is this sort of sense of shame of like, man, if—like some of these require a lot of mental fortitude and planning and patience and hard work.

Joe: Right.

Arturo: And you can just imagine what people under different circumstances with more help might have been able to do had they applied this to something else.

Joe: Yep, that’s exactly right. That’s exact—yeah. It’s entrepreneurial to do, to pull all that sh*t off and take the initiative and like, plan ahead.

Arturo: Yeah. Yeah. A hundred percent.

So behind the back walls, there was a whole nest of pipes and conduits for plumbing and electricity that went to every cell. And along with them there were catwalks to—that spread through the prison to allow for maintenance. David was able to then walk all the way from honor block through the prison laundry, and even under the next cell block. But you know, the whole prison was like a maze. So now that they were outside of their cells, David and Richard needed to find a route, uh, all the way outta prison and they needed to do it at night. Now, do you remember what tool might come in useful?

Joe: Uh, the—the glasses with the light.

Arturo: Yes, there you go.

So they were using the—the flashlight glasses they got from Tilly. Then Richard and David started planning all, uh, planning [a] way through. They slowly selected cement walls and metal grates for their escape. And then night by night, they spent time cutting holes into each one. So over time, they carved the path through the various buildings out, uh, toward the outer wall.

Tilly continued to pass them more and more tools and eventually they gave up all pretense. They—they just wanted heavy, heavy duty work gloves, concrete drill beats, chisels, more hacksaw blades and all kinds of stuff.

Joe: And no one’s noticing this? Is everyone like—Tilly’s rooting for them to get out, which is a little confusing cause it seems like she’s–

Arturo: A hundred percent.

Joe: –I don’t know, having a positive experience with them being in jail. So why does she want them to be out?

Arturo: But maybe when they’re out of jail, they can continue this on the run. Right?

Joe: I guess.

Arturo: Maybe that’s a–

Joe: She thinks they’re gonna stick around.

Arturo: I think so. I mean, by this point, if you’re so psychologically addicted to somebody, which is what it sounds like, right? Then it’s just sorta …

Joe: Yeah, it’s true. They’re probably pressuring her. Yeah, you’re right.

Arturo: And so Tilly had a unique way to get them inside, right? At home, she packed the tools inside blocks of ground beef and put them into the freezer, and the next morning–

Joe: Wait, really, beef comes back into this story??!

Arturo: Yeah, man! Dude, this is, we are sponsored by the beef industry.

Joe: Was it nearly expired beef?

Arturo: I would hope so. Let me take this little segue to thank our sponsors: N.E.M., right?—Nearly Expired Meat for all the masses. [radio ad music] “Yes, it’s cheaper than regular meat and only slightly more dangerous!”

Joe: “It’s what’s for dinner.”

Arturo: “Rotten beef. What’s for dinner.”

So she—the next morning, she carried the frozen meat into the tailor shop. Then she arranged for a prison guard to deliver the loaded meat to Richard’s cell. It went … that’s, uh—she got another prison guard to deliver the meat, that’s f***ed up. So it went without a hitch. So next time they put in an order for tools, she did the exact same thing. Now, eventually Richard and David found a steam pipe system, and that connected to a power plant outside the prison wall. So David cut a hole in the side of a pipe that was large enough for men to crawl in. And at last they had a clear path to the outside. 

CHAPTER 5: The Escape

Arturo: The final plan for the escape was drawn up like this: Richard and David would leave life-sized dummies in their beds, made from bundles of old clothes, so the prison guards wouldn’t notice they were missing.

Joe: It’s like Ferris Bueller.

Arturo: And they loved ’80s coming-of-age movies. Step two, with a guitar case full of supplies, they would climb through the hose in the back of their cells and onto the catwalk and follow the path through the walls and tunnels that led to the outside of the prison walls. They would then crawl through a manhole up to a nearby street and flee the prison. Step three: This is f***ed up. Tilly would drug her husband with narcotics that Richard had been prescribed by the prison doctors. That way he wouldn’t notice when she left in the car to pick up Richard and David.

Joe: Dang!

Arturo: Step four. When the two escapees hopped into Tilly’s car, she would drive them home, then the pair of them would murder her husband. The three of them would then collect the life insurance policy and ride right off into the sunset.

Joe: Good Lord.

Arturo: Wait, wasn’t that the whole f***ing reason that she was helping them because she was afraid they might hurt her husband? Like doesn’t—that just doesn’t—you know what I’m saying?

Joe: Oh yeah. You did say that she was scared for the safety of her husband.

Arturo: It just seems like an excuse. I think she was just all in. Also, like, the only—like how long do they think it takes to file an insurance claim? Like how were they just gonna like wait inside the f***ing house for money for months, you know?

Joe: And it—I guess then they have to make the murder look like—they can’t cut ‘em up and throw ‘em in the river. Uh, they have to do something else pretty tricky if they’re gonna get the life insurance money.

Arturo: It’s so macabre. Am I saying that word correctly? My—uh, I don’t know. Macarb?

Joe: There is no correct way to say that word

Arturo: OK. Macab-rey. It is incredibly macabre.

Joe: That was the most correct I’ve actually ever heard that word pronounced.

Arturo: So Richard and David packed their guitar cases with the necessities, pepperoni sticks, toilet paper, and electric shaver, and 40 granola bars because they were watching their figure. I’m just kidding. I don’t know why the 40 granola bars.

Joe: An electric shaver? They spent space on a shaver?

Arturo: Also—also I would’ve not thought of toilet paper, but it makes a lot of sense.

Joe: That sounds more necessary than the shaver.

Arturo: I would expect Regular Joe to think that up, you know, because Regular Joe would take a sh*t in the woods. I just wouldn’t have thought of it. Also, an electric shaver maybe to change their look. That would make more sense.

Joe: Ah, OK. OK.

Arturo: So Tilly even brought them in a compass, the New York state pages of an atlas and lots of black pepper. They were hoping to use the black pepper to keep dogs off their scent, which I have to admit, it’s pretty f***ing clever.

Joe: Does that work?

Arturo: I don’t know if it worked or not. Did it work?

Joe: I’m asking as if I—I need to keep dogs off my scent sometime.

Arturo: No, no, no. So it’s so shady. Like, every other one you’re like, “But what was the success rate for that?” So Richard gave—so Richard gave Tilly the narcotics he had saved up and the tunnels were complete and everything was ready to go. So on the night of June 5, 2015, Richard and David left their prison cells for the last time. As they made their way through their escape route, they left notes at the spots that had been difficult to overcome. At a pipe between B block and C block, they left a picture of an alien and a little tagline that said, “Are you trying me, punk?” I think they should have workshopped that tagline, to be honest.

Joe: I can’t tell if you’re joking. Is—is that—did they really do that?

Arturo: No, I’m not joking, I’m not joking. Yeah, a hundred percent.

Joe: Wow. Yeah. So they’re having fun doing this.

Arturo: They’re having fun. Yeah. Also, like, I don’t blame you, dude. Like most people’s conundrum with me is that they never know when I’m f***ing serious, you know? So I would make a terrible doctor. I’m like, “no, ma’am, you really have to go now.” They’re like, “this f***ing guy.”

At the final outer wall where they had spent 30 nights sawing through the steam pipe, their notes said, “have a nice day.”

Joe: Wow.

Arturo: Yeah. So then Richard and David got to the manhole cover, and this was it. They were free, but—[manhole cover sound]—thank you for that manhole cover sound …

Joe: Oh, we’re outside.

Arturo: Yeah. But when they popped out into the street, there was no one there. Turns out that Tilly, the accomplice and their getaway driver got cold feet. She didn’t feel so confident in the plan after all. At the last second something about drugging her husband and running off with these murderers just–

Joe: And killing him. That was part of the plan too, right?

Arturo: Yeah, it just didn’t sit right.

Joe: Good for Tilly.

Arturo: Yeah. Instead of hitting her husband with a roofie, Tilly had a panic attack at 9:00 p.m. Her husband drove her to the hospital where she was admitted for observation. Later, she would say that she never intended to drug and kill her husband. It just took her this long to finally abandon the plan. Hooo. That was really at the 11th hour there, Tilly. But that left these two escapees standing in the middle of the street at midnight with no driver and no golden life insurance policy on their side for their dumb plan. So they decided to haul ass into the nearby forests of Little Siberia. And this is where we come full circle, OK? Once they were out into the woods, they started breaking into hunting cabins. Remember the moonshine and weed and all that stuff?

Joe: Oh, yeah.

Arturo: Yeah. At one cabin they even found a transistor radio, which was lucky for them, because the cops started a huge manhunt. It was the U.S. Marshals, it was Forest Rangers, it was everybody. Border patrol, helicopters. The whole thing, right? And that’s where the two escapees split. Now David wanted to run for the border, but Richard was just done caring. So instead of heading back into the forest, he actually took a shotgun down to the road, and started shooting at passing cars, man! He hit a family camper van, and they called in the location, right?

Joe: Oh, God.

Arturo: Yeah, wildly f***ed up. But that also meant that the cops knew exactly where he was. So they closed in, and they actually killed him before he had a chance to shoot at them too.

As for David, he did try to make a break for it. But he was caught on the road to Canada before he could escape across the border.

Joe: He survived?

Arturo: Yeah—so he had been shot, but he survived. So he was brought in, and he told the story of his escape in great detail to the investigators, to the police, and to the prison officials, resulting in over 500 pages of interview transcripts. He even compared their escape to Shawshank Redemption, but he said: “Shawshank ain’t got sh*t on me.”

Chapter 6: Inspector General

Arturo: So after such a crazy escape, there was a scramble to figure out how it had all happened. Investigators interviewed 170 people to help piece together the puzzle. According to their report, there were many points of failure.

Joe: Can I just pause and be the nerd for a second? One more time? If we’re, if we—if we’re talking about, “oh, hey, we don’t have money to pay for mental health treatment of kids, that’s too expensive. How are we gonna spend that money?” OK. Cut to now X years later, the kid didn’t get mental health treatment and now how expensive do you think it is for them to be conducting this investigation with, how many people did you say they’re interviewing?

Arturo: One hundred and seventy people.

Joe: That, I mean—I, I don’t know what the number is, but that’s so expensive now that they’re, they’re having to clean up this mess that–

Arturo: So much manpower, so expensive, so deliberate.

Joe: It, it’s the—it’s the old thing of like, if you don’t want to, you know, spend a lot of money on your doctor’s bills, just like, eat healthy. And like if we just spent some money up front on taking care of people who are mentally ill, especially, like you said, kids, I thought that was a really important point you made—maybe we wouldn’t be spending the enormous budget it must have taken to clean up this f***ing mess of this gargantuan disaster.

Arturo: To take people to court, to accuse people, to, to—to interview people and then to put him back into prison, right?

Joe: The practical cold, hard, like, dollars and cents of it would actually make so much more sense if we were helping people earlier instead of trying to incarcerate and punish and sh*t later.

Arturo: A hundred percent and it’s such a powerful note to end on. My friend, that’s our story. And I hope the takeaway for our audience is that there is such a bigger conversation here about not just the prison system, but like, how … You know, it’s just really easy to wash our hands [of] people that are just, that we just see as, uh, the dejected ones from society. But it’s just so important. And also, listen, man, this is a great credit to you. I gotta tell you before we, we have to let you go, uh, we’re firing you, apparently. I don’t, I didn’t know we had hired you–

Joe: F***!

Arturo: –but you are so well versed in, in—in the business of empathy. You understand? You understand what I mean? And I think that’s a, a big credit to you, man. And I think, uh, we need more people like you in a position, in positions of power, man. And so when you, uh, run for president, I would like to put myself up for vice president! Let’s do it!

Joe: Yeah, that’s perfect.

Arturo: Let’s f***ing do it!

Joe: You and me, dude. You prez, I wanna be VP. You’re president.

Arturo: No. All right, brother. Much love to you, Joe. We’ll see you next time. Thank you so much, brother.

Joe: Love you, dude. Good to see you. Thanks everybody. Bye!

Credits

Arturo: Greatest Escapes is a production of iHeartRadio and FilmNation Entertainment, in association with Gilded Audio. Our executive producers are me, Arturo, Alyssa Martino and Milan Popelka from FilmNation Entertainment, Andrew Chugg and Whitney Donaldson from Gilded Audio, and Dylan Fagan from iHeartRadio.

The show is produced and edited by Carl Nellis and Ben Chugg, who are also, respectively, our research overlord and music overlord. Our associate producer is Tory Smith, who is our other overlord.

Nick Dooley is our technical director. Additional editing by Whitney Donaldson. Special thanks to Alison Cohen, Dan Welsh, Ben Ryzack, Sara Joyner, Nicki Stein, Olivia Canny, and Kelsey Albright.

Hey, thank you so much for listening, and if you’re enjoying the show, please leave a rating or review. My mom will call you each personally and thank you, and we’ll see you all next week.