You ever find yourself looking back at a plan and thinking, “Golly. This seemed like a lot better of an idea on paper,” — while plummeting hundreds of miles per hour out of an airplane door? At least one person we can think of might have.

Next time you’re on a plan seated in 18C, think of D.B. Cooper and his grand, mad plan.

D.B. Cooper … A Flight to Seattle … and $200,000 Cash

At 2:50 p.m. on Thanksgiving Eve, November 24, 1971, Flight 305 departed Portland International Airport on its way to Seattle — a mere 30-minute flight that would surely pass without incident, except obviously not, because here you are reading about it. [We came for D.B. Cooper. Clearly we stay for the winning repartee. -Ed.]

In seat 18C sat a middle-aged man carrying a black briefcase. He had purchased his ticket under the name Dan Cooper. Across from him sat flight attendant Florence Schaffner. Shortly after takeoff, the man known as Cooper handed Florence a note. Florence — who had in her career taken a lot of crap from passengers and was in no mood for shenanigans — surmised the note was a flirtatious advance from a creepy dude and put the paper in her handbag without looking at it.

Mr. Cooper, seeing his purpose had been misread, leaned over and whispered to Florence, “Miss, you’d better look at that note. I have a bomb.”

Of course, whispering this to her somewhat defeated the purpose of giving her the note in the first place, and he might as well have just whispered all the relevant information from that point on. Nevertheless, Florence, understandably unnerved, did take the note from her bag and read it. She found it was as Cooper had told her: The note said he had a bomb and directed her to sit next to him, which she did. Of course, at this stage, the possibility that he was just trying to get a stewardess to touch him was still a live one.

Florence asked to see the bomb. Cooper opened his briefcase and showed her the bomb, which she observed was indeed a bomb — or at least a bundle of red cylinders that looked exactly like what a bomb is supposed to look like. Cooper then asked the flight attendant for a favor: Could she possibly see her way clear to getting him $200,000, four parachutes and a fuel truck standing by at Seattle’s airport to refuel the plane?

Florence said she’d see what she could do, and went and told the pilots there was a situation.

After contacting the airport, and telling the other passengers their flight would be delayed by a “minor mechanical difficulty” — which the smart passengers would’ve seen right through after watching the weird guy in 18C muttering to the stewardess sitting next to him — the pilots circled Seattle for two hours while down on the ground money and parachutes were gathered.

During the flight, Cooper was extremely pleasant and well-mannered, speaking politely to the flight crew and paying for his drinks — rather than asking them to deduct it from the ransom money.

Finally, the plane landed, and the rest of the passengers were let off while it was refueled, after which Cooper announced to the crew they were all going to Mexico and the margaritas would be on him. With the money and parachutes safely delivered, the Boeing 727 took off again, heading for Reno, Nev., where it would refuel once more before heading to Mexico City.

However, the plane had not yet reached Reno when Cooper ordered all the crew into the cockpit, tied the money bag around his waist, opened the door and jumped. It was dark and raining, and jumping was an extremely stupid thing to do, and the fact he was never seen again may be related to this.

In 1980, some of the ransom money washed up on the bank of the Columbia River near Vancouver, Wash., which only added to the mystery of what happened to the hijacker. Police thought it unlikely he had survived the jump, especially considering of the two parachutes he’d taken with him, one was a dummy used for classroom demonstrations and didn’t actually work.

Still, it’s possible he got lucky with the other parachute — though where he’d disappeared to, in the Northwestern wilds, if that were so … well that was a mystery.

And it’s remained a mystery to this day. Who was this man? It’s unlikely his real name was Dan Cooper. It’s even less likely his real name was D.B. Cooper, the name attached to him due to misreporting at the time. Numerous possible suspects have been suggested, but none has been proven to be the man himself.

It’s nice to think that maybe Mr. Cooper is still out there somewhere, living his best life, kicking back with a bourbon and Coke and reminiscing about his most awesome day ever.

D.B. Cooper Route Map

For some reason, hearing this story always makes this author think of hazing, and how that might impact one later on in life. One might, for example, end up jumping out of a plane in the middle of some desolate place with $200K neatly tucked away. Of course the money would be completely useless in that circumstance — unless one jumped with a lighter too, perhaps. The human brain can be a strange thing. Some people (say, D.B. Cooper) simply were not born for strategy. … We did actually pick a photograph for the header that represents one of the forest areas between Portland and Seattle. All in all, it does not look a fun landing spot for skydiving at night in bad weather. Should you be wondering about the seemingly small amount of money for which ol’ D.B. Cooper went to all this trouble, it might help to know that in 2022 dollars that represents about $1.4 million. Of course a single Warhol painting of Marilyn Monroe just sold at auction for $195 million, so all and all, it might have been easier to just jump with that.

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