The problems with the hunt for D.B. Cooper
Some thoughts from the new Netflix documentary on one of America's most legendary unsolved mysteries
By now you know the legend. A neatly-dressed man in dark sunglasses named “D.B. Cooper” boards a plane, passes a note to a flight attendant demanding four parachutes and $200,000 in cash, then jumps out the back of the plane with the cash, vanishing into the middle of the night somewhere over the woods of the Pacific Northwest, never to be seen again. Remarkably, there are no hostages.
Half a century and more than 1,000 cleared suspects later, the FBI’s still stumped. The mystery has grown into mythology. A new documentary out, D.B. Cooper: Where Are You?, is Netflix’s take on what happened, how this mystery man became a pop culture icon, why so many people are inspired to solve the case themselves, and why they’ve all come up empty so far.
The four-part series centers mostly around Robert Rackstraw, an ex-military paratrooper believed to be Cooper, and the pursuit of a former TV executive Tom Colbert out to prove he’s the guy.
I want to believe Colbert is in the ballpark because Rackstraw never denies that he’s Cooper, even when asked point blank, “Are you D.B. Cooper?” But I want to believe there’s a simpler explanation for what happened.
I believe whoever Cooper was, he was an ex-Boeing employee commissioned by either an expert stick-up crew or some crafty drug traffickers, and he had multiple guys on the inside helping him pull off the stunt. The demands he made, such as the four parachutes, and the specific instructions about how to fly a plane, such as going down to 250mph at a low altitude, are oddly specific. That convinces me that this was a guy who knew how the plumbing worked. And $200,000 might not be able to franchise an Arby’s, as the doc jokes, but it can “clean” a lot of fronts for you.
We know that several media initially identified him as “D.B.” instead of “Dan” by mistake, and that’s how the name stuck. Whether or not he could have survived the jump (more on that later), the “D.B.” mistake put out by the media became something of an inside joke among the crew who were more than happy to let the legend grow into Boogeyman-like folklore as a perpetual taunt to the FBI (“Sure, he could be out there! He could be any of us! We are all D.B. Cooper at heart!”).
Remember, when the guy bought his ticket, he signed in as “Dan Cooper”, which is the name of a French-language comic book series about a fictional fighter jet-flying hero in the Royal Canadian Air Force. As one amateur sleuth points out in the doc, if a guy robbed a train under the alias “Tony Hawk” and escaped on a skateboard, you’d never think that was a coincidence, would you?
The crew that pulled off this job was cocky and was more than happy to antagonize authorities over the years. That’s why “D.B.” sent letters out with mysterious coding. I believe Rackstraw, who died before the doc came out, knew some of the crew, and took delight in not getting in the way of a fun narrative when people asked him about it.
I have no skin in this game. I’m just trying to look at lines, not dots.
Which brings me to my first point. There are a lot of lessons here about the art of research that any of us can apply to our own work. The way I see it, there are four things getting in the way of this investigation, and why it remains unsolved:
1. It’s working from too many assumptions
Because this was such a risky jump, there’s an assumption that whoever did this had to have specialized training. This leads investigators to focus on ex-military guys with parachuting experience who broke bad. And that’s how we end up zooming in on the life of Rackstraw, a decorated Vietnam veteran highly skilled as a pilot and paratrooper, who left the Army months before Cooper’s hijacking.
In later years Rackstraw was charged with, and acquitted of, murdering his stepfather. He also once stole an airplane and faked a crash to avoid an embezzlement trial against his ex-wife. Rumor has it he was a CIA operative involved in Iran-Contra.
Those anecdotes alone are worth their own movie. He settled down later in life, earning a law degree and teaching in the University of California system. When Colbert confronts him, offering cash for his story, Rackstraw is running a marina outside San Diego.
Early on, the doc looks at Dick Briggs, a drug trafficker who went around claiming to be Cooper in the 70s. In one scene, a close associate tells a story of Briggs sitting at a bar telling people he was Cooper — and to prove it, he pointed to a couple across the room and declared they’d find some of Cooper’s money in a few days. Sure enough, five days later the couple’s son finds it buried in the sand near the ocean.
Briggs is ruled out as a suspect because of his lack of flying experience, and unfortunately, we don’t get closure on this because he died under mysterious circumstances in 1980.
I have a question: Why are we so convinced the person making this jump was an expert?
How many daredevils do you know with a military background?
Every day in the United States, thousands of people go skydiving. You don’t have to be an expert to do it. But you do have to be completely fearless (and a little bit crazy).
Red Bull TV is consistently amazing late-night binge-watching. It’s always showing a documentary of some adventure enthusiast attempting something crazy, like jumping off a cliff in a wingsuit or climbing massive rock structures with no ropes. These aren’t people who stormed Normandy. They’re mostly free spirits with a Bohemian lifestyle.
Which is to say, why are we ruling out the idea that the hijacker wasn’t highly trained?
How many times have we seen this in the movies? The clues to a crime lead a detective down one path, only to discover the perpetrator was who they least expected at the outset. This applies to real life, too. Some of the most famous manhunts in American history worked on assumptions that turned out not to be true.
Heck, why are we assuming this guy survived the jump in the first place? At least a few theorists believe he didn’t survive. It was dark out, the weather was crappy, and the plane was flying over a thick forest. If he jumped in a suit and dress shoes, he was not properly equipped for a friendly landing.
Or, given the massive attention, could he have been killed by someone in the months after the hijacking, out of a fear he might talk to authorities?
At one point it’s pointed out that Colbert had assembled 91 pieces of evidence, but none of them a smoking gun. Which leads to the next problem:
2. It suffers from pareidolia
This is a phenomenon defined as “the tendency to perceive a specific, often meaningful image in a random or ambiguous visual pattern” — in other words, how we tend to see shapes or pictures out of randomness.
The third episode is titled “Seeing Jesus in the Toast”, alluding to a news story a few years ago of a woman who saw an image of Jesus Christ in a piece of toast. It’s a great analogy for the confirmation bias that’s thwarted the countless sleuths who thought they were close to solving the case.
A while back I read a really interesting article on Medium from David Gamble, on a recent phenomenon of people seeing images of what looks like a smartphone in 17th-century paintings, as evidence of time travel.
Those images, of course, are something else entirely, like a prayer book or a pocket mirror. This is textbook pareidolia 101. Gamble warns:
When faced with an amazing claim (ghosts, gods, ESP, aliens, bigfoot, etc…) you would be wise to step back and appreciate that what you are being presented with is a wholly subjective sincerely held interpretation and not an objective truth. We all interpret things in the context of our cultural expectations. There are no exceptions, it is the way we are and is part of the human experience, we all do this.
The problem with documentaries like this is when the story of the mystery instead becomes the story of some unhinged “internet sleuth” who thinks they’re Columbo. Too many of these docs don’t play enough referee with the crazy, because the producers think they might have the next Tiger King on their hands.
Colbert tries really hard to make this story about himself. At some point, the story veers away from Colbert’s discoveries and into Colbert’s determination to be right, even if the pieces don’t add up. It never made sense to me why Colbert put so much of his energy (and money) behind this. He doesn’t have a personal beef. It’s not like the guy hurt one of Colbert’s family members or something.
By the end of the final episode, it seems like Colbert is more motivated by the fame of being the one who cracked the case than cracking the case itself. His team brings a lot of experience to the table, but Colbert is also trying to sell a story. Unfortunately, he’s trying to sell a quarter-inch drill bit where there’s no quarter-inch hole.
3. It suffers from “The Curse of Dimensionality”
This law of probability is a recurring problem in statistics, and in turn machine learning, explained by Seth Stephens-Davidowitz in his book Everybody Lies.
Essentially, if you track enough data points, you’ll eventually find a relationship between two of them even if it’s inconsequential. An example Stephens-Davidowitz lays out:
Suppose your strategy for predicting the stock market is to find a lucky coin — but one that will be found through careful testing. Here's your methodology: You label one thousand coins — 1 to 1,000. Every morning, for two years, you flip each coin, record whether it came up heads or tails, and then note whether the Standard & Poor's Index went up or down that day. You pore through all your data. And voila! You've found something. It turns out that 70.3 percent of the time when Coin 391 came up heads the S&P Index rose. The relationship is statistically significant! Highly so! You have found your lucky coin!
Just flip Coin 391 every morning and buy stocks whenever it comes up heads. Your days of Target T-shirts and ramen noodle diners are over. Coin 391 is your ticket to the good life!
Or not.
Here’s a clearer example: Suppose you come up with an algorithm that can pick out the best-qualified candidates for your job opening based on their resumes. Let’s say more often than not, the top candidates are named Bob. Does this mean you should eliminate a good candidate because their name is Bill?
Therein lies the problem with Colbert’s investigation. Because he’s working on a bias, and because he’s gathered so much evidence that seems a bit circumstantial, it leads him to treat loose connections as absolutes.
We meet a man named Rick Sherwood, a Vietnam vet who knew Rackstraw, who thinks he’s solved the case after decoding one of Cooper’s mysterious letters.
Sherwood, well-versed in code languages from his time in the Army, applies a technique called “Simple English gematria”, taking letters and converting them to numbers. A equals 1, B equals 2, and so forth. You add the numbers up, and the thinking is that if two phrases add up to the same value, they must be related.
The last line of the letter says, “And please tell the lackey cops DB Cooper is not my real name.” Sherwood finds the first half of that sentence, “And please tell the lackey cops” adds up to 269. Same as “I’m LT Robert W. Rackstraw.” This convinces him that Rackstraw is Cooper.
Neat trick, except for the fact that 269 also adds up to “I am SpongeBob SquarePants”, as another investigator points out.
You see this all the time with conspiracy theorists. Because they so badly want to believe a conclusion, they’re willing to accept weird little synchronicities as ironclad instead of coincidence.
4. The police sketch does nobody any favors
There’s this brilliant Saturday Night Live sketch from the mid-1990s, during the apex of the Unabomber manhunt, where Norm MacDonald plays the artist behind the Unabomber’s infamously nondescript sketch being interviewed on a TV news station.
In Norm’s trademark deadpan absurdism, he says the hood and sunglasses never came up in any eyewitness interviews, but he’s not good at drawing hair or eyes, and “a good sketch artist knows his limitations and uses various techniques to compensate for them.” He then shows some of his other famous sketches of wanted men still at large, including “The Ten-Gallon Hat Killer” and “The Chef Hat Killer”.
The whole thing is laugh-out-loud hilarious. I can’t help but think of this every time I see that sketch of D.B. Cooper. Really? Dozens of eyewitnesses and that’s the best you can do? A well-dressed man in sunglasses?
No wonder the FBI’s still stumped 50 years later. With a rendering like this, they were already down two touchdowns in the first quarter.