This Happened to Me: I Flew a Plane with Zero Training

This is a story in our This Happened to Me series, which is based on our long-standing adventure comic first published in 1940.

I WOULD NOT be here, behind the complicated controls of a Cessna single-engine airplane droning in the dark 7,000 feet above Interstate 35, ferrying a butchered whitetail and millions of dollars in paper checks, were it not for my brother’s golden tongue.

As the lights of Des Moines glowed on the horizon, and I wondered how I’d land this plane, my brother’s words took on new meaning. “Enjoy the ride,” he told me when I boarded this plane on a dark tarmac in East St. Louis, Illinois. “It’ll be an adventure.”

But Hugh was back on the ground, and my only companion besides my rising anxiety was my copilot, asleep in the seat next to me. The problem: He incorrectly assumed I knew how to fly. Worse, he also thought I knew how to land.

Hugh, my junior by nearly two years, was working those days at Love Field, the Dallas airfield most people know from the assassination of President Kennedy. It was on Air Force One, parked at Love Field, that Lyndon Johnson was sworn in as president in November 1963, and it was at Love Field that Hugh combined his love of airplanes with his almost pathological gregariousness. Hugh was incapable of meeting someone casually. Instead, he found a way to become fast friends with even passing acquaintances.

It’s how he came to know his wife, by fueling her charter plane at Love Field—an origin story that spawned years of off-color jokes at family gatherings. And it’s how he buddied up with a squadron of pilots who crisscrossed the country every night delivering paper checks from Federal Reserve banks to a big data-processing center in Columbus, Ohio.

hunters pose around truck bed with deer
The author (right) with his father and brother and their deer. Courtesy of Andrew McKean

It occurs to me now, in this age of digital banking and electronic funds transfers, that what I’m about to describe is from another century. I guess it was. This was in about 1992, when you paid your rent and bought your groceries not with debit cards or touchless digital transactions but with paper checks. All those millions of checks that were written on any given day, from Yakima to Tallahassee, were bagged up and flown overnight to Columbus, where funds were transferred via some warehouse-sized mainframe computer. These overnight “check flights” were the circulatory system of America’s banking infrastructure, and the pilots who flew this ghost fleet of contracted planes didn’t have uniforms. They were generally young, trying to accumulate hours aloft so they could graduate to airline jobs.

It also occurs to me now how poor I was at the time. I was living in Seattle, working as a newspaper editor and barely making enough to buy gas and pay rent. But it was deer season back home in Missouri, and I reckoned I had just enough money for a one-way Greyhound bus ticket. Hugh told me that he’d get me back to Seattle on a check flight.

EVERYTHING went as planned. I slummed across the country on the “Dirty Dog,” Hugh picked me up in Columbia, Missouri, and as we drove together to the family farm, he told me more about the check flights. They’re modern-day cowboys, he told me of these young jet jockeys. When they travel off the clock, they never fly commercial; instead they just take the jump seat in each other’s planes when they want to get somewhere. I’d be welcome to get back to Seattle on the check-flight network. In fact, he had arranged that I’d start my trip from East St. Louis.

Back at the farm, we ate mom’s home cooking, helped my dad vaccinate calves, and each of us shot a deer. I wanted to take as much venison back to Seattle as possible to supplement my diet of beans and rice, so the afternoon of my departure, we butchered my deer, wrapped prime cuts in plastic, and stuffed them in my backpack. I felt glad for Hugh’s connection, mainly because it was free, but it also meant I wouldn’t have to worry about checking my awkwardly heavy luggage on a commercial flight.

The actual embarkation felt like a drug deal. Sometime around 10 p.m., we found the dumpy airport, and Hugh went into the terminal to talk to someone. Before I knew it we were driving his car onto the unlit tarmac and pulled right up to a high-wing Cessna. Hugh exchanged some words with the pilot and then waved me over. I manhandled my heavy backpack to the plane, heaved it in the fuselage along with canvas bags that I guessed contained checks, and then Hugh hugged me farewell. “Enjoy the ride. It’ll be an adventure.”

The pilot got me settled in the right-hand seat, started the engine, and just like that we were off to Kansas City, where we picked up more bags of checks. Then the pilot got us off the ground and pointed north toward our next stop: Des Moines. We were still climbing when he said through the headset that he had paperwork to do.

It took me a second to realize he was handing over the controls, and another second to realize Hugh must have indicated that I was a fellow pilot. For the record, I am not now and I certainly was not at the time. I took the yoke and continued the climb, but I also didn’t know what altitude to level off at. I recalled from the St. Louis-to-Kansas City leg that we flew around 7,000 feet, so that’s what I aimed for, but I was so conscious of watching other instruments that I didn’t realize that I had climbed above 9,000 feet. The pilot was lost in paperwork and thrashing AC/DC tunes and didn’t seem to recognize my mistake, so I pushed the yoke in to descend. Suddenly the plane’s angle changed and the nose started barreling toward I-35, which I recognized from my boyhood in Missouri.

“Then I saw the glow of Des Moines and my enjoyment vanished, replaced with a bleak terror. I’d have to land this plane.”

The pilot looked up from his clipboard in the half-darkness of the cockpit. “Seventy-five hundred’ll be good,” he said, and went back to his work. I leveled off and for a few minutes actually enjoyed myself. The land of my youth was cloaked in thin clouds, which amplified the lights of each town along the interstate. There was Cameron, and St. Joe off to the west, then Bethany. I wondered if I could see the lights of the farm away east as we got close to the Iowa line, my sleeping parents oblivious that their unpracticed son was flying his deer meat high overhead.

Then I saw the glow of Des Moines and my enjoyment vanished, replaced with a bleak terror. I’d have to land this plane. The pilot was now asleep, best as I could tell, and our destination coming on fast. I recalled the airport was in the southwest corner of the city and started losing altitude, much slower this time. Which way was the wind blowing? What would my approach be? How would I be in touch with air traffic control? Should I tell the tower that I was going to try an emergency landing? Should I buzz the airport first just to get the lay of the land? All these thoughts were racing through my mind when the pilot stirred. He glanced at our heading and the instruments, and sat up straighter in his harness.

“Got it,” is all he said, and I felt the yoke get lighter, an indication in the dark that he had taken it.

We landed without incident and taxied up to a Learjet. My companion went into a low concrete building and came back with two other pilots.

“These guys will take you the rest of the way,” he told me, then leaned in close as I stepped out of the plane. “Maybe we don’t mention this to anybody, okay?”

I helped transfer bags of checks from the Cessna to the jet, and stood on the tarmac, backpack pushing down my shoulders, as I waited for directions. It was just past 2 a.m. The jet jockeys told me there were only two seats—“for the pilots,” they said with some emphasis. I was welcome to ride in back with the checks.

So I threw my backpack in on the pile of canvas bags, climbed in myself, and we were off, first to Lincoln, then Denver, then Helena, Montana, before a bumpy ride to Portland. The sun was just coming up as we flew low into Seattle. I had dozed off for a spell, my back leaned uncomfortably against my pack. For the first time in hours, there was enough light that I could assess my surroundings. I was draped across untold wealth inside all that canvas, but I also noticed something else: red splotches on the bags. My backpack was leaking deer blood.

As we parked on the tarmac and the pilots opened the hatch, I arranged the check bags so they couldn’t see the stains. I walked into the light, happy to be on the ground and happy for many meals of meat. And also happy to pay commercial fare for my next cross-country flight.

Read more OL+ stories:
I Should Have Died in a Floatplane Crash
This Happened to Me: I Almost Froze to Death on a Solo Bighorn Hunt