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D.B. Cooper committed one of the most famous heists in American history. This true story is packed full of unanswered questions and strange mysteries.

Cooper hijacked a plane at 30,000 feet and forced it to land in Seattle to pick up $200,000 —which in today’s currency, would be around $2,000,000 — and four parachutes. He then jumped out of the plane with the money, never to be seen again.

Did he survive the jump from the plane? Did he go on to live a long and full life afterward? Was he mentally ill, or a criminal genius?

In this episode of The Art Of The Exit, we asked all of these questions — and even found some answers. We spoke to experts on the subject to learn more about what happened on that stormy night in November of 1971 and the mysteries that followed.

The Art Of The Exit by Yahoo Finance is a true crime podcast that goes inside the most notorious heists in history. Listen here, and subscribe for a new episode coming next week.

“There is the myth of the Cooper case, and the facts of the Cooper case,” Geoffrey Grey, who studied the Cooper story for years and eventually turned it into a best-selling book, says in the episode. “I think he was someone who was super troubled. He was not some sort of cowboy or counterculture figure.”

The year is 1971. Richard Nixon is president. The U.S. is still in Vietnam, and the Space Race is in full swing. Paranoia in the nation is at an all-time high but ironically, airport security is extremely lax these days. You could smuggle just about anything onto a plane back then, and that brings us to the airport in Portland, Oregon, on Thanksgiving Eve.

There's a 30-minute flight set to head north to Seattle when a man named Dan Cooper purchases a one-way ticket for $20. He uses cash. Cooper's appearance has been described as ordinary for that time period except for what onlookers described as "manic behavior." He wears a basic suit with a clip-on tie. He makes it to his seat while chain-smoking cigarettes without removing his sunglasses. He makes those around him uncomfortable even before the plane takes off.

After the flight attendant, Florence Schaffner, drops a bourbon and soda at Cooper's seat, he hands her a note. Men passing notes to women was common then. Schaffner stuffs it in her pocket, thinking it is just another man taking a pass at her. She is wrong. "You'll want to read my note, miss," Cooper says. "I have a bomb in my briefcase."

The folklore of the story tends to lean more on Cooper as a hero instead of villain. It’s easy to get caught up in the cinematic side of the story, especially remembering how everything seemed to fall perfectly into place for him to escape.

“I’d say he’s more lucky than genius,” Tom Kaye said in the podcast. “He was a gentlemen though. He tried tipping the flight attendants after he got the money. He wasn’t a hardened criminal. This seemed like something he was forced into doing. A do-or-die scenario.”

The question at the foundation of the story is: Was Cooper some sort of vigilante? Or was he a madman who got lucky? Did he even survive when he jumped out of a moving passenger plane?

No matter where you land, it is irrefutable that this story is anything less than extraordinary.

Listen to his story on The Art Of The Exit now on Apple Podcasts or Google Podcasts

Full transcript of the episode below:

Alex Sugg (00:02): On November 24th, 1971 a man cheated death. Not only did he outsmart an entire system, but he also got really rich in the process. For over 40 years people have been searching for him, but his true identity remains a mystery to this day. He jumped from a plane that night, having become the first and only successful air robber in history, and has never been seen again. How has he continued to slip through our fingers for over four decades, and what happened that night on the plane? This is the story of DB Cooper. From Yahoo Finance, this is the Art of the Exit. I'm Alex Sugg.

AS (01:03): So, let me give you some context. The year is 1971. Richard Nixon is president. The U.S. is still in Vietnam, and the Space Race is in full swing. Paranoia in the nation is at an all-time high but ironically, airport security is extremely lax these days. You could smuggle just about anything onto a plane back then, and that brings us to the airport in Portland, Oregon on Thanksgiving Eve. There's a 30-minute flight set to head north to Seattle when a man named Dan Cooper purchases a one-way ticket for $20. He uses cash. Cooper's appearance has been described as ordinary for that time period except for what onlookers described as, "manic behavior." He wore a basic suit with a clip on tie. He makes it to his seat and chain smoked cigarettes without removing his sunglasses. He made those around him uncomfortable even before the plane took off.

AS (02:06): After the flight attendant Florence Schaffner drops a bourbon and soda at Cooper's seat, he hands her a note. Men passing notes to women was common then. Schaffner stuffed it in her pocket, thinking it was just another man taking a pass at her. She was wrong. "You'll want to read my note, miss," Cooper said. "I have a bomb in my briefcase." Schaffner unfolds the paper which reads something like, "I want $200,000 dollars and two sets of parachutes." He later took the note back from her as to not leave any evidence behind. He was good at covering his tracks. Cooper's demands were expected in Seattle when they landed. He threatened that if the demands were not met, he would blow up the plane. "No funny business," he repeated.

AS: 02:56 After Schaffner read the note, Cooper asked her to sit next to him. He opened his briefcase to show a mess of cables and red cylinders. He then restates his demands. He wants $200,000 dollars, which in today's currency would be around $2 million dollars, and four parachutes, and a fuel truck ready to fuel the plane upon arriving in Seattle. They were not going to stay on the ground. She took his demands and shared them with the pilots. This was the beginning of a very, very long flight.

Geoffrey Gray: 03:36 Now enter the air terminal in Portland, Oregon.

AS: 03:41 I spoke with Geoffrey Gray, a former reporter who spent years studying this case which he later turned into a bestselling book.

GG: 03:49 You have a passenger who immediately gets noticed by some other passengers, and why? He's very fidgety, he's chain smoking, he's in a suit and tie. He's sitting off to the corner. He looks basically, according to the FBI report, like a troubled dude. The flight itself takes off as scheduled about 2:47, I think, in the afternoon to Seattle. Just a 30-minute ride. Super, super short flight, and he's one of the last passengers to board. Again, there was just something up with this guy in the back, and he's holding an attache case. He had sunglasses on. He looks like a weird person.

AS 04:26 So you said there was a vibe about him before he got on the plane, and then once he got on, he was noticeable to those around him in a negative context. He was giving off a vibe like he's a little bit weird or something is going on with him. So people noticed him before the flight.

GG: 04:44 Absolutely, and that's one of the things that you find in the DB Cooper case is there's the myth of the Cooper case, and the facts of the Cooper case. One of the things that I was able to stumble on after getting access to these original FBI case files was the actual 302s, the actual reports of passengers. They immediately noticed him, or some of them, in Portland before the plane even started.

AS: 05:08 Florence Schaffner, she gets the note. She opens it, she tells the pilots what's going on. Can you tell me a little bit about what is happening with the other passengers onboard? What is the mood on the plane? Are they aware of what's going on? Is it a general, almost like a hold up, everyone is aware that it's a hostage situation? Or, is it more contained than that?

GG: 05:32 Yeah. You know, the mood on the plane was, "What's going on here? We have no idea. Why are we circling for three hours? I just want to get home and to my family." The pilots made up some excuses over why they were being held up, and really what was going on on the ground was a roundup of parachutes and cash to meet the hijacker's demands. It was incredible that nobody really picked up on it until well after. It was incredible, and maybe for a good reason, that there was really no panic.

AS: 06:01 Right.

GG: 06:02 At this time, nobody was really aware that there was a guy maybe with a bomb in the back threatening to not only blow the plane up, but ransom on the passengers, and jump out with parachutes.

AS: 06:14 Why was this flight chosen? Was there a reason?

GG: 06:19 You have to ask Cooper why he chose this specific flight, but the general consensus is that it was a Boeing 727, which had aft stairs, stairs in the back, that you could actually release during flight and jump out of folks did in Vietnam with the same plane.

AS: 06:36 That leads me to another question of, he must be keenly aware of how planes work. It's clear that he has background in planes. That must narrow the search pretty dramatically, right?

GG: 06:49 No. Cooper displayed knowledge of aircraft and knowledge of parachutes, but unfortunately you think that that would narrow down the search, but to what degree did he have the knowledge? Was he a licensed pilot? Was he a manager? It's still unclear. Was he a professional parachutist, or was he in the Special Forces or the military? There's some clues but the clues were not specific enough to really get a specific kind of profile.

AS: 07:18 Is there a chance that he died from the jump, that he maybe didn't make it? I mean, it seems unlikely only because they would have recovered a body, but is there any possibility of that? I'm not sure if he knew the weather conditions or what was going on that night, if you've dug that research up.

GG: 07:37 Yeah. So this is the fundamental question in the Cooper case is, did he make it, or did he even survive the jump, or is he hanging from a tree in the Great Pacific Northwest? There's two schools of thought. People who follow this case, there's one camp or the other. I'm of the opinion that the drop zone of the flight was actually not quite in a forested area, but it was farther south in wine country, the Livermore Valley and that Cooper could have likely survived the jump. Furthermore, experts say that if he did do the jump with the parachute that he had, at the very least he could have broken a leg. It was not quite as perilous of a jump as we all imagine.

AS: 08:21 After circling the air for hours, Cooper jumped from the plane and escaped. The time and location of when he jumped couldn't be confirmed by anyone onboard, making his landing zone almost impossible to pinpoint. As Geoff said, the fundamental question at the base of this whole story is, did he survive that jump? If he died upon landing or if he got caught in a tree, wouldn't somebody have found a trace of that by now? All signs pointed to the idea that he did in fact survive that night, and even more so that he continued living and hiding for the next few decades. I had to ask Geoff the obvious question. Who do you think did it? Who do you think is DB Cooper?

GG: 09:12 Who's DB Cooper? Well, I think he's somebody who was super troubled. I don't think that he was a heroic cowboy or a counterculture figure. I think that he was somebody suffering from severe paranoid schizophrenia or depression. I think that anyone who hijacks a plane, it's an act of both murder, an act of suicide, there's so much going on there that the stable don't really do it, and don't really always do it for money too. There's this hidden motivation. So, I'm looking for somebody that fits that category. Somebody who is ready to just check out of life, and it's more of a tragic hero. I wouldn’t call him that, I don't think he's a hero. He's someone who put lives at risk. He's a criminal. He's a dangerous person, but I put him more in the tragic psychological depressive loner state.

AS: 10:12 Was Cooper mentally unwell? Was he depressed? It's an extremely plausible assumption that Geoff made about Cooper. I mean, what does it take for somebody to commit a crime like this? I have to admit, I get caught up in the cinematic sides to this story pretty often myself. It's way easier for me to frame Cooper in a brave or valiant light, but this was a crime that put real people at risk. A guy had a bomb on an airplane. The realization that this person was willing to lose life over this is a pretty sobering way to remember this story. No matter how miraculous the whole event may seem. After the break, we'll look at the only pieces of evidence found in the case, and we learn about how Cooper treated his hostages.

AS: 11:09 Initially, it was believed that Cooper's jump from the plane was in a remote area of Southwest Washington. This region was searched on foot and helicopter without a trace of Cooper or his parachute. The exact location of where he jumped has countless variables attached. The aircraft's speed and the weather conditions alone are enough to make this landing site a total mystery, not to mention, no one onboard had precise timing of when he jumped at all. What makes this case so interesting to me are the seemingly perfect circumstantial and environmental elements it took to pull this off. It feels so unlikely that every element of that night aligned to assist Cooper pull off this amazing crime, but the alternate is equally unlikely. If Cooper did die that night, how is it possible to have no evidence of a body or a parachute all these years later?

—

Tom Kaye: 12:16 Tom Kaye.

Alex Sugg: 12:17 Hey, Tom. This is Alex. Tom Kaye is a paleontologist from Arizona. He was hired by the FBI to examine evidence they believed was connected to Cooper. This is him telling me about a bird skeleton he's been researching for the past couple of weeks.

TK: 12:32 Bird fossil. It was 1.2 inches long, the whole skeleton. So the question was, was the thing running when it was out of the egg, or was it nest bound and taken care of by the parents?

AS: 12:42 There's never just one possibility with Tom, and that's what makes him good at what he does. He doesn't jump to conclusion without facts to back it up. It's a great strength when you're looking at all of the outcomes to account for in the Cooper case.

TK 12:57 No, the DB Cooper case is an interesting sideline because of all of the mysteries. This one has some rare characteristics. Number one, it actually happened. The fact that this happened and that it's the only unsolved skyjacking in US history makes it unique. Also the fact it was long enough ago that they couldn't apply modern forensic techniques to the case, but not so long ago that evidence is gone. Evidence is still available.

AS: 13:31 Okay. So when you were working on it, what exactly were you doing?

TK: 13:36 Well originally I was contacted because the FBI had never analyzed the money that was buried. So as a paleontologist, I study things that have been buried in the ground for a long time. So although the connection doesn't make sense at first, when you explain it that way, it makes a little more sense.

AS: 13:54 What were some of the interesting findings you had with it?

TK: 13:54 Well there were three bundles of cash. They were $20 dollar bills, and they knew it was Coopers money because the serial numbers lined up. The money remains probably one of the bigger mysteries in the Cooper case because we can't connect the dots between where he jumped in Ariel, Washington 20 miles away and how you end up on and there's money under the sand.

AS: 14:15 What percentage would you say is likely that he survived the jump out of the plane?

TK: 14:20 We'd say at this point in the game very likely. So back in the day, jumping out of a plane at 200 miles an hour seemed like it would shred the parachute, or you would get disoriented. It was dark out, there was clouds, it was raining. So there was a lot of reasons back then to say that he didn't make it. When you jump out of an airplane at 200 miles an hour, the chute does not open right away. It does what we call squidding. So you'd slow down there. You could make that jump, but I think he's more lucky than genius. He was not the first guy to jump out of an airplane like that, he wasn't the last. So he gets all the credit but he by no means thought it up all on his own. He may have, but there was other people that've done it before him. They just all got caught or died in the process.

TK: 15:08 I think he was luckier than smart. He took some precautions but didn't take others. He was a gentleman though. He had food brought in for the pilots knowing it was going to be a long trip. He tried to tip the flight attendants, and they turned it down. They turned down the money. When he got the money he was so happy he tried to give them some, and they said, "No, we can't take tips," which they were chided on afterwards saying, "You should have gotten some of the money back." So, he did not act like a hardened typical criminal that didn't care about anybody. He really seemed that this was something he was forced into doing. It was a do or die scenario.

AS: 15:54 Tom Kaye, thank you so much for your time.

Alex Sugg: 16:14 This case leaves a lot to mystery. In my findings, I realized that when you don't have a person but just a profile, it's easy to assume different things about it. Some people believe Cooper was a mentally ill man who lost control and recklessly committed this crime. Others believe he was a sort of vigilante who gave a giant middle finger to the system, to the law, and even took the matter of getting rich quickly into his own hands. Cooper's story has created a massive range of devoted followers. A simple search online and you'll find countless people either claiming to be Cooper, or claiming he was their uncle, or a parent, or some distant friend of the family, et cetera. There are city wide events where sunglasses, a black suit, and a clip on tie are the party dress code. There's even a music festival based off of his escape. No matter where you lie on the spectrum of Cooper and what kind of man he was, it's irrefutable that this case be seen as anything less than extraordinary.

AS: 17:27 It's amazing that in all this time, no definitive evidence has emerged to show whether Cooper lived or died that night. In July of 2016, the FBI shut down its investigation into Cooper indefinitely. It's a symbol of closure. There is a very high chance we will never know the identity of the man who was DB Cooper. People will continue to search and dig, but it would take some extraordinary evidence to show who he was at this point. This person who's lived among us for 40 years. He could be in your very town. He could be down your street.

AS: 18:12 All these years later living a quiet life and still looking over his shoulder, wondering if today is the day he actually gets caught. In a strange way, I don't really want to find out who he was after all. When it's all said and done, all the right and the wrong, the genius or the sheer luck of this story, a part of me thinks keeping DB Cooper's identity a mystery is better than discovering who he really was all along. This man will die one day, but DB Cooper, the myth and the story, will live forever as one of the greatest heists in history.

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