The Man Who Walked Backward

An American Dreamer's Search for Meaning in the Great Depression


By Ben Montgomery

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From Pulitzer Prize finalist Ben Montgomery, the story of a Texas man who, during the Great Depression, walked around the world — backwards.

Like most Americans at the time, Plennie Wingo was hit hard by the effects of the Great Depression. When the bank foreclosed on his small restaurant in Abilene, he found himself suddenly penniless with nowhere left to turn. After months of struggling to feed his family on wages he earned digging ditches in the Texas sun, Plennie decided it was time to do something extraordinary — something to resurrect the spirit of adventure and optimism he felt he’d lost. He decided to walk around the world — backwards.

In The Man Who Walked Backward, Pulitzer Prize finalist Ben Montgomery charts Plennie’s backwards trek across the America that gave rise to Woody Guthrie, John Steinbeck, and the New Deal. With the Dust Bowl and Great Depression as a backdrop, Montgomery follows Plennie across the Atlantic through Germany, Turkey, and beyond, and details the daring physical feats, grueling hardships, comical misadventures, and hostile foreign police he encountered along the way. A remarkable and quirky slice of Americana, The Man Who Walked Backward paints a rich and vibrant portrait of a jaw-dropping period of history.





Never mind how far he got.

What it is, is the tilt of the hat.

—Dodie Messer Meeks

Dear reader,


Plennie Wingo died in poverty in the fall of 1993. He was buried in Wichita Falls, Texas, about 180 miles from my hometown of Slick, Oklahoma. I first heard of him in 2013 while researching unconventional pedestrians. A few years later, when I could not forget him, I decided to try to write a book. The first thing I did was buy a Clason's Touring Atlas, circa 1931, one of the first ever made, so I could follow in his footsteps to see what he might've seen, and to see how we've changed. One note about change: to avoid littering the text with calculations, I've left it to you, dear reader, to put dollar amounts into familiar context. So, $1 in 1931 is equal to roughly $16 in 2018; $5 then is $80 now; $10 is $160; and so on.

I've tried my best to tell his story true. Nothing in this book is fabricated by me, including the dialogue. If it's in quotes, it comes from a historic document or Plennie Wingo's own humble account of his trip. I've tried to tell the story of that dark period true, as well. For that reason, and because we are occasionally mean to one another, you should be aware that this book depicts quite a bit of violence.


Thank you for reading,



Those Golden Days

Sunrise, West Texas.

Time of morning when the dead black gives up to the first throws of yellowpink in the east, out beyond Fort Worth and Dallas, past Shreveport and Jackson and Montgomery and Savannah. A man here in Abilene walks this morning, like every morning, down a bone-dry farm-to-market road outside town. He is out before the sun because he walks backward, that is to say, he walks in reverse, and he chooses this time so he may behave in this odd fashion cloaked in darkness lest his neighbors see and cast judgment upon him, make him for crazy. His own mind is fairly certain on the point, but he'll admit there is room for doubt.

He is not a brilliant man. Some would say he does not even encroach on smart. But inside his balding head he has a bold idea, and sometimes when a certain kind of man has a certain kind of idea, one that he considers good, that good idea takes hold of him and it swells up behind his eyeballs and expands, balloonlike, so big that it crowds out all the other thoughts and ideas, and it becomes the one thing he thinks about, the only thing. Such is the case with Plennie Lawrence Wingo, who is nearly penniless but full of ambition just shy of his thirty-sixth birthday and a hair short of what would be one of the worst years in American history.

The idea has become an obsession, though he's not ready to admit that just yet. He thinks of it when he wakes in the morning and it follows him all day long, and when he closes his eyes at night he is wrapped completely in the blanket of his vision.

The idea is why he walks. It is why he walks backward.

Five miles some mornings. Ten, others. Hours alone in the last gasp of night, scooting retrograde across the long shadows drawn on the dawning landscape, the place they called the Great American Desert, Llano Estacado, past the roadside tufts of buffalo grass and thickets of honey mesquite, the reaching lechuguilla rods and smoke bush and angry explosions of butterfly weed. Backward across the land from which they pulled oil until that went bust; the land upon which, before the oil, they raised cattle until that too went bust; the land from which, before the oil and the cattle, they harvested buffalo bones, full skulls and skeletons that once gave shape to the great roaming beasts of the Plains, the givers of tools and food and warmth for the natives, and, after them, fertilizer for the white men in sweat-stained cowboy hats who stacked their bones like cordwood, building white hills head-high and as far as you could see. The bones brought twelve to fifteen dollars a ton to any man resourceful enough to pile them high, and they were plentiful in Abilene, the epicenter of this macabre market for three hundred miles in most directions. They took the bones, then the beasts, then the oil beneath, and then it was all gone. What was next for the taking was anyone's guess. What else was left?

Now the town near which he walks holds abundant life, or at least enough to advertise to the outside world. The rising sun in the east outlines its elegant business structures and its beautiful, commodious homes, its apartment houses with up-to-date Frigidaire refrigeration, its magnificent public buildings and institutions like the Abilene State Hospital for Epileptics and Simmons College, its model school buildings, three now, its federal post office and courthouse, its compress, its oil mill, its electric light plant, its ice factory, its impressive fairgrounds, its artificial lake, its parks, its paved boulevards, its railways, and, pitched against the weak sunlight, its Paramount Theatre, built this very year, 1930, its grandeur unrivaled between El Paso and Fort Worth. To think that so much had sprung forth from nothing but dry Texas dirt in just fifty years.

That same dry dirt chalks his teeth and cakes his forehead, and his garments show signs of a man who has put in a full day's work by the time most are beginning to wipe sleep from their eyes, drag on their trousers, and start the percolator. He thinks about them, how they'd whisper if they ever caught sight of him out here, all alone and going backward. How they'd wonder what he was up to, what kind of crazy had gotten hold of him. They would, of course, ask him, Why? Over and over again, Why are you doing this? Even now, he is formulating his response.

He has not known a full day's work in some time. They'd talk about that, too, for sure. How his lot had soured. How they'd read about his troubles with the police in the paper. Another reason he is here, backpedaling in the dawn.

He hoped they'd remember the good times and his good name. He'd experienced high days, sure, when his future seemed full of promise. He was a man of business for a time, resourceful, straight as a preacher on Sunday.

His professional life in Abilene began six years before, in February 1924, at age twenty-nine, when he struck a lease deal with C. Hall for the north half of the lower story of the Morgan Jones building at 127 Chestnut Street, in Abilene's busiest district, for a monthly payment of $65, and opened a restaurant soon after. He was P. L. Wingo, owner of the Crescent Café. Those golden days.

Then, in March of '27, looking for a bigger slice, he signed a lease with C. C. Tate, renting the basement beneath Tate's Dry Goods store on Lots 1, 2, 3, 4, 5, and 6, at the corner of Chestnut and South First Streets for a sum of $30 a month on the promise that Mr. Tate would build a staircase from the basement to the first floor so customers could use the water closet. He was then P. L. Wingo, owner of the Mobley Café and Dining Room. Glorious days.

He swept floors and bused tables and counted dollar bills. He served meat-and-threes to tenant farmers and ham and eggs to country lawyers and fried squash to the ladies from the Baptist church. The city directory called him proprietor and the humble newspaper advertisements he ran beckoned the hungry, the conservative, the children. There is no better way to make mother happy than to take her to a nice lunch room for a Sunday dinner.

Things were good for Plennie Wingo. Things were good for most everybody.

In the blink of the last few breakneck years of that roaring decade, something incredible happened. Something happened that had never happened before and would never be repeated. Books would be written, scores of them, about the era of vision and optimism and boundless hope.

Who knows exactly where it started, but if you back up a bit, you can see the boom taking shape. Archduke Franz Ferdinand fell in 1914. Germany sank the British liner Lusitania in 1915. Ten million American men walked to their local polling stations in the summer of 1917 to register for the war Woodrow Wilson had finally decided to enter. Fifteen days later, Newton D. Baker, Wilson's secretary of war, stuck his hand into a goldfish bowl containing 10,500 numbers and drew out a black capsule marked No. 258, drafting into service one man from each precinct across a country that was not at all ready for the First World War.

If this was the sowing of the seeds of hope, maybe its roots took hold in one of those foreign foxholes filled by one of those 24 million American doughboys along the Paris-Metz highway or in Murmansk or Romonofska. Or maybe it was back home, where the women planted victory gardens in public parks and went to work in huge numbers for the first time on assembly lines in factories, building trucks and munitions for shipment overseas. Maybe its first shoots emerged from the soil after 17 million soldiers and civilians had been killed abroad, when the American men came home—some disengaged and disenfranchised, all having passed the first big test of loyalty in a young multicultural nation—to a newfangled communal exaltation conjured by a government trying to dampen nationalism abroad and fuel it at home: the patriotic parade.

They marched stone-eyed down American boulevards and heard tell they were heroes. Some of them believed it.

Whatever the building blocks of the prosperity to come, when Warren Harding was elected president in November 1920 by the smallest turnout of voters in American history, he did something that set the tone for the next decade in a country weary of war and scares and moral rebukes. He gathered his clubs and balls and played a round of golf.

"America's present need," the former small-town newspaperman said, "is not heroics, but healing; not nostrums, but normalcy; not revolution, but restoration; not agitation, but adjustment; not surgery, but serenity; not the dramatic, but the dispassionate; not experiment, but equipoise; not submergence in internationality, but sustainment in triumphant nationality."

What followed was optimism, and mass production, and the mass production of optimism. The city skylines rose and invention burst and productivity soared. Henry Ford turned out a new car every ten seconds and the nation's first network of dealers rose up to sell them, followed quickly by a vast web of paved roads, traffic lights, hot dog stands, repair shops, and filling stations, allowing the weekend adventurer to drive the countryside confident that he wouldn't wind up spending the night stuck in a rut or searching for a spark plug. Almost as quickly rose a nationwide network of antennae and broadcasting stations and hookups to pipe the phenomenon called radio into homes across America. Advertisers immediately lined up to introduce a Happiness Boys song with a quick pitch about insurance or greeting cards, a controversial new offense on family circles called a "commercial."

If you looked at a graph that mapped economic ebbs and flows of the decade, you'd see a jagged but lofty incline starting in 1923 and growing yearly toward a glorious mountain of prosperity. The United States was on its way to manufacturing 43 percent of the entire world's products, and the advertisements in the new glossy national magazines like TIME made a man want one of everything.

A pretied bow tie, a pair of fringe-tongued Mayflowa brogues, and a Jordan roadster in the garage. "Somewhere west of Laramie, there's a bronco-busting, steer-roping girl who knows what I'm talking about," smooth-talked the Vanity Fair ad for the latter. "She can tell what a sassy pony, that's a cross between greased lightning and the place where it hits, can do with eleven hundred pounds of steel when he's going high, wide and handsome. The truth is, the Playboy was built for her. Built for the lass whose face is brown with the sun when the day is done of revel romp and race. She loves the cross of the wild and the tame.…"

And Campbell's, by God! Campbell's was making twenty-one different kinds of canned soup. Not just tomato and beef and pea soup—you could get ox tail soup, turtle soup, mutton soup. Some Plennie Wingo couldn't even pronounce. Julienne? Printanier? Consommé?

By 1925, American capitalism churned like a hungry machine. The number of manufacturing facilities in the United States had skyrocketed and the worth of that output sprang up. In just five years, industrial production had nearly doubled. Bellwether radio sales, which accounted for $60 million in American spending in 1922, grew 1,400 percent.

"No Congress of the United States ever assembled…has met with a more pleasing prospect than that which appears at the present time," said President Calvin Coolidge, who had taken over from Harding and whose name would become synonymous with "prosperity," in his last message on the State of the Union to Congress in 1928. "In the domestic field there is tranquility and contentment…and the highest record of years of prosperity."

This wasn't a speculative splurge like in 1637, when Dutch venturers saw wealth in tulip bulbs, or 1720, when Parisians lost their shirts hoping to find gold in Louisiana. It wasn't the real estate bubble of 1814 or untamed speculation in canal investment in 1830 or the railroad boom of 1873. The economy was buoyant, profits endless.

"The main source of these unexampled blessings," the president said, "lies in the integrity and character of the American people."

Business earnings soared. Big corporations ate smaller ones whole. The market gave birth to powerful companies like United States Steel Corporation, International Harvester, and American Tobacco, and gave rise to a wealth of utilities, food retailers, variety stores, motion picture theaters, and chain retail stores like Montgomery Ward, American Stores, and Woolworth, companies built to last.

And men dumped their money into investments and reaped the profits hand over fist. They threw money at the stock market, as much as they could scrape together, and became proud shareholders in companies that were great and some that were phony. They flocked south, with income and access never before available, and bought subdivided land in Florida, sight unseen, both waterfront properties with golden views and worthless mosquito-filled tracts of muck and detritus, and called it all paradise. Then they sold it for a profit. These new playboys and sun worshipers didn't need to be coaxed to buy in. They needed an excuse. And even the swamp had value.

Never before had so many become so stupendously, so painlessly, so expeditiously rich.

They were happy. They were credulous.

And there stood Plennie Wingo, whose father died when he was a baby, whose mother married his uncle and bore ten more children, who learned to read and write and saved his money and opened a shop to cash in on the swirling American adventure. He was a self-made man at a time when the business of America was business, as the president said. The businessman, someone else said, was the dictator of destiny, ousting the statesman, the priest, the philosopher. The Man Nobody Knows, which cast Jesus of Nazareth as "the world's greatest business executive" and the parable of the prodigal son as the world's greatest advertisement, topped the best seller list, and the optimistic autosuggestion that "Day by day, in every way, I am getting better and better" was on the lips of men everywhere. It was an age of improvement, and Plennie was riding shotgun, all angular youth and bootstraps. He had a house in the city and a wife who loved him and a young daughter to whom he could one day leave his fortune. He leaned in the doorway of his café before the crowds trickled in, one hand in his pocket, a smile on his face, his necktie tight, shirt starched stiff, and his spit-shined wing tips planted firm on the productive earth of a country oozing with promise.

That was then. Now he scoots in reverse. The sun creeps up and the shadows shrink as he wipes sweat from his face and picks up his pace. If he could walk backward through time itself, he would. He should've seen the signs. He should've known the men were coming for him, because they came for everybody.

They came on March 17, 1928, first to the dusty town of Pecos, 240 miles west. Fourteen strong-jawed lawmen and two federal prohibition officers seized 610 gallons of mash and whiskey and a 300-gallon still, then captured four ruffians on a ranch just over the New Mexico line and threw them in the Reeves County Jail, charged with supplying the whole damn West with strong drink.

They came again on April 7, 1928. Squinty-eyed border patrol officers down south in desolate Del Rio confiscated 628 quarts of tequila and cognac in one of the largest liquor hauls anyone could remember.

They came to the region time and again that year, doling out enough liquor charges to fill entire columns in the morning newspapers. They popped George Stringer of Abilene for transportation. Arrested Bud Moore of Abilene for possession. Collared Fred McCasland of Abilene for both.

The pace of takedowns was the talk of Abilene, and folks wondered if the harassment was simply the last gasp of the teetotaling arbiters of amusement. They wondered, after nearly a decade of Prohibition, after seeing the illegal booze market boom almost unchecked, whether anyone of import would have the political will to keep up the charade. By 1928 the issue at last found its way into a presidential campaign. New York governor Al Smith, running for the Democrats, didn't like the ban and had big ideas to change it. Herbert Hoover was considered a dry, though he left room for interpretation, calling Prohibition "a great social and economic experiment, noble in motive and far-reaching in purpose," which "must be worked out constructively."

The American people, for their part, abstained or kept good secrets, or read in the local newspaper about those who couldn't do either. In Texas, substantially more than half of all cases brought to court in 1928 revolved around booze: the making, the selling, the carrying, or the drinking.

So ubiquitous was intoxicating liquor and so close behind was the legal trouble in February 1928 that T. H. Millhorn was charged with possession, sale, and transportation. Millhorn was operator of the Southland Hotel, at 917 South First Street. And if a ten-year-old girl stood in front of Plennie Wingo's café, she could throw a bottle of Waterfill and Frazier and hit the Southland Hotel.

He should've seen them coming.

The disappointment was fresh in his mind two years later, and when he closed his eyes he could still feel the click of the handcuffs around his wrists, the shame of his escort to the Taylor County lockup, the sting of the headline in the Abilene Morning Times.

Liquor Cases Are Pending Against P.L. Wingo Here

Restaurateur P.L. Wingo, 33, was bound over Tuesday afternoon to await the action of the grand jury on a liquor complaint in which he is charged with selling and possessing intoxicating liquor.

Thus he became one of the 55,729 liquor cases brought to court in the United States that year. The grand jury was cold, and the bond $750, more than two years' rent on the café. It was terrible. Terrible, but not impossible to overcome. A black eye, but not a knockout for a man obliged to do better and better. With enough sweat and traffic, he'd be back in the black in six months, a year tops. People had money to spend and Plennie was ready to trade them for fried chicken.

In early March 1928, the market surged up and stayed there. The tight-lipped Federal Reserve Board met daily in Washington, fifteen hundred miles from Plennie Wingo's limping café in Abilene, and no one knew exactly why. By the end of the month the tension was unbearable and people began to sell their stock. Favorites like Wright Aero and American Railway Express were dropped like they were hot. Things got worse as a wave of panic swept the market. Folks sold in astonishing volume and prices plummeted.

But the market steadied, then rose, then rose some more, as though the quick drops had shaken out those who lacked the will to play it for eternity. Up it went, and smart observers noted that there had been a mighty revolution in industry, trade, and finance, and that the stock market was but an indicator of those tremendous changes in progress. People took to calling it a Big Bull Market. Herbert Hoover latched the Republican ticket to the wagon and rode it into the White House, crushing Al Smith in both the popular vote and the Electoral College. And in accepting the presidency, he reflected what many must have felt in their souls in those heady, lofty, optimistic days.

"One of the oldest and perhaps noblest of human aspirations has been the abolition of poverty," he said. "We in America today are nearer to the final triumph over poverty than ever before in the history of any land."

Plennie Wingo was listening.

"The poorhouse," Hoover said, "is vanishing from among us. We have not yet reached the goal, but, given a chance to go forward with the policies of the last eight years, poverty will be banished from this nation."

The audacity. The pomp. The language. It was all absolutely perfect for the moment. It was also very, very wrong. So wrong that Hoover—a Horatio Alger–esque multimillionaire who would later be summoned to service by more presidents than any other American chief executive, who was awarded more honorary degrees than any other American, whose relief efforts are said to have saved more human lives than those of any other individual in all of human history—would be defined by and remembered for how wrong he was.

And what comes next sets the stage for our story.


By the time Hoover was having the very first telephone installed in the Oval Office, the financial system had become so entangled and convoluted, the securities-absorbing investment trusts and branch offices of Wall Street trading firms so numerous, the ticker so overworked, that few had any real idea what was actually happening. But the massive majority did not care. They expected whatever was going on to keep on going on, and someday they would cash in that American Can stock and think themselves wise. The skies would be full of airplanes, the roads full of shiny new cars, and poverty would be a forgotten social ill of a bygone era.

Then, in early September, the market broke. The drop was short-lived, and by midmonth averages were back up. Then it slipped harder, and by early October most watchers knew something was wrong, though they weren't sure what. They remained optimistic, outwardly at least. The pointy-heads at the Harvard Economic Society said that "despite its severity, we believe that the slump in stock prices will prove an intermediate movement and not the precursor of a business depression." Iron output was slower. Steel production was off. Fewer cars were selling and fewer were coming off the line. Home building was down. Freight-car loadings fell. Nonetheless, "the conditions which result in serious business depressions are not present," said the head of the Cleveland Trust Company. "Unless we are to have a panic—which no one seriously believes—stocks have hit bottom," said the director of McNeel's Financial Service. "The industrial situation in the United States," said the chairman of the National City Bank of New York, "is absolutely sound and our credit situation is in no way critical."

What came next was monumentally bewildering and frightening to anyone paying attention. What came next, on the morning of Thursday, October 24, 1929, was liquidation. Prices dropped. Dropped fast. Dropped hard. Dropped vertically. Dropped with an unprecedented and riveting violence. Dropped so mercilessly that outside the stock exchange, a roar rose into the morning air as a crowd gathered on Broad Street. As the New York City police arrived, a workman appeared atop a building to do some repairs. The hysterical crowd had made him for a suicide and was encouraging him to jump.

The hysteria bled into the next week.

Stocks were selling for nothing. Weren't selling. Rumors spread like wildfire. A suicide wave started, and eleven well-known speculators killed themselves. Two men with a joint account jumped hand in hand out a window in the Ritz. An investment firm ran an ad in the Wall Street Journal that read: "S-T-E-A-D-Y Everybody! Calm thinking is in order." Police fished the body of a commission merchant out of the Hudson River—his pockets contained $9.40 and some margin calls. Desk clerks in New York hotels, it was said, were asking guests if they would be using the room for sleeping or jumping.

The market fell and fell until the news at last, slowly but surely, reached the rest of the puzzled nation around the time the market finally stopped its monthlong slide in the middle of November.

In Abilene, there were no runs on banks in those early days. They were paving a new stretch of Highway 30 and playing host to a conference of Methodists, and the Majestic was showing The Saturday Night Kid, a talkie starring Clara Bow, James Hall, and Jean Arthur. But Plennie Wingo read the bleak and foreboding reports.

Midwestern livestock was selling slow in Kansas City, with the chief influence cited as a "sluggish, depressing beef trade." Fort Worth livestock wasn't even selling. Cotton was down. Grain was haunted by reports that Europe was overloaded with breadstuff supplies, and the Chicago wheat market suffered material setbacks in prices, which "bumped into a stone wall," as a reporter put it.

The seams had come apart.


  • "Wielding both the big brush historical context and fine comb of biographical detail, Montgomery's text reads as good literature, taking a seemingly peculiar stunt and drawing out the humanity of the man and his era. All American history readers should wander and wonder with Wingo, whose tale is elegantly sketched out here."—Jeffrey Meyer, Library Journal (Starred Review)
  • "Engaging...In clean, briskly paced prose, Montgomery follows Plennie's journey, and he walks the reader backward, too, into the history of America in the 1930s and before."—Colette Bancroft, Tampa Bay Times
  • "Ben Montgomery is a joy and a wonder, a writer I would happily follow halfway around the world -- backward. In fact, I just did, in the compelling company of Plennie L. Wingo, the retrograde ambulator of Abilene, Texas. What a book!"—David Von Drehl, author of Triangle: The Fire That Changed America and Rise to Greatness: Abraham Lincoln and America's Most Perilous Year
  • From Rip Van Winkle to Forrest Gump, Americans have fallen in love with quirky individualists who find their true worth by lighting out into the territory. They were fictional. Plennie Wingo, the man who decided to walk across the globe backward, was real. Wingo turned his back on the Great Depression, an adventure brought to life by the vivid narration of Ben Montgomery, a writer so talented I could read him walking backward."—Roy Peter Clark, author of Writing Tools
  • "In The Man Who Walked Backward, Ben Montgomery lovingly assembles a mosaic of the United States and the world between the wars, told through the life of a small-town Texan who refused to accept his miserable lot during the Depression. Montgomery's vivid storytelling resurrects the strange and wonderful Plennie Wingo, a new American Everyman."
    Andrea Pitzer, author of One Long Night

On Sale
Sep 18, 2018
Page Count
304 pages
Little Brown Spark

Ben Montgomery

About the Author

Ben Montgomery is a former enterprise reporter for the Tampa Bay Times and founder of the narrative journalism website In 2010, he was a finalist for the Pulitzer Prize in local reporting and won the Dart Award and Casey Medal for a series called "For Their Own Good," about abuse at Florida's oldest reform school. He lives in Tampa with his children. He is the author of The Man Who Walked Backward, The Leper Spy, and Grandma Gatewood's Walk.

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