An Occasional Hobo

Josiah Flynt Willard’s Journey from Tramp to America’s Leading Expert on Hoboland to Enemy of the Tramps
Riding the Rails, Excessive Use of Stimulants, Harry Houdini’s Childhood Home, Doting Mothers, Unceasing Cussedness, Remorse Best Not Described, Pocketfuls of Doughnuts, Drubbings and Other Hardships, Wayward Boys, Swampy Things, Tolstoy’s Tobacco Addiction, Hapless Persecution, Riffraff, Circus Men, The Sensation of Being Vainly Hunted, Tamerlane’s Tomb, Shudderful Joy
by Robert Ito
Willard in his “Garb of The Road” in St. Petersburg, ca. 1895. Image from Willard’s My Life, 1908.

An Occasional Hobo

Robert Ito
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In 1900, Josiah Flynt Willard, writer, amateur ­sociologist, and sometime hobo, published Notes of an Itinerant Policeman. In the book, he describes the often-unsavory world of fin de siècle American tramps: their begging strategies, their caste systems and codes, their hot tempers and underdeveloped intellects, their reasons for becoming tramps in the first place (number one: liquor). One of the book’s more compelling chapters is entitled What Tramps Read. This is one facet of tramp life one might not immediately think of, but its inclusion in the book makes a lot of sense. Because, really, who has more time to read than a tramp? As it turns out, they’re not all that different from the rest of us. When young, they like “dime novels and stories of adventure”; later, they graduate to pulps, for their “spicy articles and glaring pictures.” Detective stories are popular, as are the works of Charles Dickens, Victor Hugo, and William Thackeray, even if, as one tramp tells Willard, Vanity Fair could have been much improved had it been “choked off in the middle.”

One author these wandering readers might not have cared for, however, was Willard himself. At nineteen, the Illinois native embarked on an eight-month tramp through several states, riding the rails, begging for meals and clothes, learning the hobo’s arcane language. Over the next decade, Willard entered college, left college, tramped through Germany, Italy, and Russia, met Ibsen and Tolstoy, then tramped some more. Under the pen name “Josiah Flynt,” Willard wrote ­stories of his adventures for magazines and journals of the day. By the time Willard published his first book, Tramping with Tramps, in 1899, he was the country’s foremost ­authority on the subject. Van Wyck Brooks, ­Pulitzer Prize–winning ­author of The Flowering of New England, called him the Audubon of the tramp world. Jack London dedicated his own tramp diary, The Road, to Willard, describing him as “the real thing, blowed in the glass.”1

In his works, Willard ­neither romanticized tramp life nor defended it. If, as Todd DePastino noted in Citizen Hobo: How a ­Century of Homelessness Shaped America, “Willard challenged the middle class’s conventional wisdom about tramps, overturning fearsome stereotypes that had been born ­during the crisis years of the 1870s,” it was hardly intentional. For Willard, these men and boys were lost souls: too lazy to work, too cowardly to steal, addicted to tramping in the same desperate manner that others became hooked on alcohol and ­tobacco. Willard was a lot like them, as one might ­expect, and shared many of their shortcomings, most notably, a near-­insatiable “go-­fever” that called to him ­throughout his relatively short lifetime. “For nearly forty years,” Willard wrote, “I chased the Beyond—that misty and slippery sorceress, ever beckoning ­onward to the wanderer, yet never satisfying, never showing herself in her true deceitful colors, until after long years of acquaintance.”

It was this ambivalence toward tramping that brought Willard to lead the most peculiar of ­double lives. At twenty-eight, after years spent riding the rails, Willard became a railroad “bull,” spying on and ratting out his former colleagues as a patrolman and detective. When he wasn’t pursuing them, Willard wrote about them, denouncing them in newspapers and journals as the basest of men. “At the bottom of their hearts,” he wrote, “they know that theirs is a low world, boasting nothing that can compare with the one which they criticize and carp at.” He called for restrictions on their travel, and more brutal jail sentences for the lawbreakers among them. All the while, he befriended them, supped with them. In at least one instance, a fellow tramp saved his life.

When Willard died in a ­Chicago hotel room at thirty-seven—“condemned to an early death by an excessive use of stimulants,” one friend wrote—a flurry of post-­mortems followed. Friends and peers remarked on Willard’s uncanny ­ability to transform himself from the man they thought they knew into someone, something, unrecognizable. With but a change in his gait and the way he moved his hands and eyes, a shift in speech so that the listener “could scarce ­understand one word in five,” Willard, the acclaimed author, became “­Cigarette,” American hobo. Following his death, ­colleagues wondered whether the man had “gone native,” or simply lost himself in his adopted role. None of his friends, however, commented about his transformation from friend of the tramps, and a tramp himself, to one who had few moral qualms about hunting them.


Willard was born in 1869 in Appleton, Wisconsin, the childhood home of Harry Houdini and site of the state’s first telephone. His father, Oliver Willard, was editor in chief of a daily newspaper; his mother, Mary Bannister Willard, was the daughter of a divinity professor and a devout Methodist. Willard was small for his age, with delicate features and a mop of thick brown hair. In a photo taken when he was thirteen, the boy appears no more than nine or ten. His mother doted on him, and he on her. “When after supper mother had settled herself in one of the large chairs near the stove, I would climb into her lap and say: ‘Hug me, mother, I need it,’” he wrote. “Probably no lad ever needed mothering more than I did.”

At the age of four or five, Willard was beaten by his nurse “for some slight offense.” The boy fled his home and attacker, eventually ending up on the village’s main street. “No child ever had a greater measure of unalloyed joy in his soul than I did when I dashed down that ­village lane,” he recalled, “and no later escapade has ever brought me quite the same fine shade of satisfaction.” It was Willard’s earliest ­memory, and his account of it is like that of a junkie after his first and best fix, the high forever chased after but never attained. Before long, a police officer found the boy and took him to the local prison, which doubled as the town’s fire station. Willard’s confinement was an easy one, much of it spent eating candy in the station’s engine room. “Nevertheless, it was imprisonment of a kind,” he wrote of the ordeal, “and I knew it.”

In 1877, Willard’s father died. Willard, who was eight at the time, remembered little about his ­father beyond an incident in which he loudly cursed his displeasure ­after sitting on a brood of newborn ­kittens. Willard’s mother and grandmother took on the task of raising him. The following year, Willard was smoking, cussing, lying, and “pilfering,” causing such a stir in town that neighbors warned their ­children to steer clear of the troublesome boy. A friendship with a much larger schoolmate earned Willard a reputation as a scrapper. He was not. One friend described him as “a little, thin, white, shriveled creature,” and his tenuous status as a fighter rested largely on his bullying of his tough-looking pal. “I was continually on the watch not to risk my reputation in any fair struggle,” he wrote.

Willard ran away often, ­despite repeated whippings and ­entreaties from his mother and grandmother. “The longing to go,” he wrote, “would come upon me without any warning in the dead of night.” Forced stays in a small town in western Nebraska—“A good ­roughing-it may bring him to his senses,” advised a family friend—and at an Illinois boarding house did little good. “When I think of my almost unceasing cussedness throughout [my mother’s] struggle,” he wrote, “a remorse comes over me which is best not described.”

Not all of Willard’s cussedness came on the road. “Indeed, I recall a most cruel thing I did to a little baby girl, living near our old brown house,” he wrote. The girl was the baby sister of a friend, two or three years old, “a chubby little creature with fat, red cheeks, and large blue eyes like saucers.” When no one was looking, Willard would steal into the girl’s room and pinch her cheeks, hard, over and over again, until she wailed out in pain. “As I look back over the disgraceful affair now, it seems to me one of the insanest things I ever did.”

In 1884, Willard’s mother and sisters left for Europe. The boy was sent to a small Illinois college, where he excelled in history and modern languages. An essay contest, one of the biggest events of the school year, became an obsession for Willard, who spent every spare hour “religiously devoted to that wonderful essay.” On the night of the contest, the trio of competitors faced the judges. By
Willard’s account, his essay was the finest, his friends assuring him that he had won “hands down” over his two outmatched foes. He finished third. Inconsolable, Willard holed himself up in his room. The president of the college came one day to cheer him up, but to no avail. Willard left school the following day, never to return.

The ensuing years were unremarkable ones. On a whim, ­Willard stole a horse and buggy “standing idle in one of the thoroughfares” of Buffalo, New York, for reasons “I cannot say, even now.” After selling them to a friend, he stole ­another. The constables soon arrested him, and Willard was sentenced to a year in reform school. After a matter of months, he and three of his schoolmates made their escapes. A ­local farmer and his wife clothed and sheltered Willard and filled his pockets with sandwiches and doughnuts. The next day, Willard made his way to West Virginia and freedom. He was eighteen. “I realized, after a fashion,” Willard wrote, looking back on those times, “that my youth was considered pretty much a fiasco.”

Thus began Willard’s eight-month tramp, a journey that would form the basis of many of his later writings and cement his reputation as America’s leading expert on Hoboland. It was 1888, a time when the railroads were crawling with all manner of vagabonds. Construction of rail lines had exploded during the Civil War, and the recent Depression of 1873–1879—the real Great Depression, as it is now sometimes called—sent an army of out-of-work men and boys onto the tens of thousands of miles of track crisscrossing the country. Willard was like many of them: young, restless, prone to crime. Other aspects of his situation, however—his schooling, his privileged upbringing, his access to money should things ­become dire—set him worlds apart.

Willard’s tramp began humbly enough, at a cluster of coke ­ovens in Pennsylvania. “My boots had been exchanged for shoes, the old cap had given way to a better one, and the ragged coat had been patched,” he wrote.2 “In this fashion I climbed to the top of the ­ovens and said ‘Hello!’ to some men who were cooking their coffee in a ­tomato-can over one of the oven openings.” The tramps ­offered Willard coffee, bread, and meat, and taught him how to fashion a makeshift bed out of planks. Over the next few months, he learned hobo etiquette (when to speak, and, more important, when not to); how to get a decent night’s rest in boxcars and haystacks; where to locate the “fattenin’ up places” where hobos could get a square meal. He begged and stole, got shot at by an angry conductor, fell off a train and lived. “He went through every sort of privation,” a friend wrote, “endured dirt, accustomed himself to the society of every variety of his fellow-creatures, without a murmur or regret.”

When the need arose, he fought, although he had neither the skills nor the heart for it. “I had more than once to rescue him,” remembered Alfred Hodder,3 who was ­coauthor, with Willard, of The Powers That Prey (1900), about graft in New York City. “He had the height and body of a slim boy of fourteen, but just to see what the beast would do he would have teased my lord the elephant, and he took a drubbing as naturally as any other hardship.”

By the end of his eight-month sojourn, Willard was a changed man. “It had steeled my muscles,” he wrote, “tightened up my nerve, and jostled my self-reliance into a thoroughly working condition.” When asked, years later, if the experience might be beneficial for other wayward boys, Willard had no ­concrete answer—it depends on the boy, he said. The Road had taught him “many desirable truths,” but he warned others from it, except as a means of revealing how much better the “main Road” could be. It was “not to be recommended,” he wrote. “It is a backwater section of our civilization; it is full of malaria and other swampy things.”


Exhausted, underweight, and “tired of simply ­drifting,” Willard looked eastward, to Europe. Things couldn’t be any worse there than here, Willard reasoned, and, besides, his mother lived in Germany, so he would have a place to stay. After working his way across the Atlantic as a coal passer 4 on a steamship, Willard made his way to Berlin. His mother welcomed him, fed him, bought him a new suit and hat. Willard slept a great deal and put on some of the pounds he had lost aboard ship. His mother’s library provided him with reading materials aplenty: David Livingstone’s ­Missionary Travels and Researches in South Africa, John Stuart Mill’s Principles of Political Economy. “I frequently caught myself looking about the library,” he wrote, “with its pleasant appointments, and wondering whether my wanderings were not, after all, simply a nightmare.”

In 1890, Willard entered Berlin University, where he began a PhD in political economy. At that time, all that was required of foreign ­students was twenty marks for the matriculation fees; “nothing was asked about your former studies or ­academic training.” After two years, the Road beckoned once again. Willard traveled to London, where he met ­Arthur Symons, a British writer and critic. The two became friends. On one occasion, Symons told Willard that he had just received fifteen pounds for a magazine article, which seemed a princely sum for something as easy as writing. Willard rushed a tramping story to a British magazine, and it was accepted. A new life opened up for Willard, one in which tramps begat stories, ­stories begat articles, and articles begat cash—cash which was then used to fund the next tramp. Willard ­began recounting his experiences in the pages of the Atlantic Monthly, Century Magazine, and Harper’s.

Over the next six years, Willard took frequent breaks from school to travel to England, Switzerland, Italy, and Russia. Tramps, he called these trips, but they were nothing like the ones of his childhood. Thanks to his mother’s money and connections and the learned friends he made through Symons, they were largely pleasant things: A climb through the Swiss Alps.5 A four-month stay in Venice, then on to Rome and Naples. A trip to Russia to chat with Tolstoy, who discussed the Bible (he liked the parables) and his former addiction to tobacco. A brief, largely uninteresting audience with Ibsen in Munich, who asked ­Willard about his family, his travels, his opinion of Germany. Free railroad passes appeared, as if delivered by fairies; introductions and meals arrived from sources unknown. Willard would chat up the local tramps on occasion, or not. Tramping ­became more of a diversion, something to do to find ­material for his next story, rather than the addiction it had once been.

In 1896, Willard took part in a police raid on Dom Viazewsky, a slum in St. Petersburg. Earlier, he had told a local chief of detectives that he would like to see “how his men ‘worked,’” and the chief was happy to oblige. “In a way, it was got up for my benefit, I fear,” wrote Willard, “and I was later very sorry about it all.” As Willard looked on, a small army of detectives and patrolmen laid siege to a “suspicious” lodging house. Poor souls staggered out of their bunks clad only in rags; youngsters “quaked with fear” at the surprise late-night raid. One old man mistook Willard for an officer and showed him “a greasy scrap of paper”—his passport. “There was an appealing look in his faded, ancient eyes,” Willard wrote, “like that in those of a mongrel who would fain beg your mercy.”

In one night, Willard had gone from sometime tramp to—what? Hapless persecutor? Innocent observer? There are any number of ways that Willard could salve his conscience about the ordeal. The raid would likely have taken place eventually, he could tell himself, with or without his prompting. But when Willard got the call to go, he neither complained nor balked. He went along, then got paid for writing about it. The experience disturbed Willard, but not overly much. “The scene told the sad, sad truth about Russia,” he wrote, ­cryptically. Two years later, Willard himself would be a railroad bull, rousting folks on his own, making his once-fellow tramps “quake with fear.” Was this raid, this elaborate show, arranged for Willard’s edification, the turning point that set him on his path as enemy of the tramps?


Shortly after his return to the United States in 1898, Willard received a letter from famed railroad executive L. F. Loree6 asking to meet with him “on a matter of business.” “The thing
I had in mind to do, and have tried to do,” Loree told Willard, “was to clear the property intrusted to my hands of that riffraff population which has been infesting American railroads for so many years.” Loree had a proposition for Willard. As an employee of the railroad company, Willard would return to his old tramping ways, traveling undercover and informing on his fellow tramps. In addition, he would spy on the railroad boss’s own detectives to ferret out just why they had been making such a hash of the job themselves. Loree was asking Willard to be a rat, two times. Willard’s response: What’s a job like this pay?

The offer was a fulfillment of a weird, long-standing dream. “For a number of years it had been a wish of mine to have an experience as a police officer, to come in contact with tramps and criminals, as a representative of the law,” Willard wrote. “Not that I bore these people any personal grudge, or desired to carry out any pet policy in dealing with them; but I had learned to know them pretty intimately as companions in ­lodging houses and at camp-fire, and had observed them rather carefully as ­prisoners in jails, and I was ­anxious to supplement my knowledge of them with an inquiry in regard to the impression they make on the man whose business it is to keep an official watch over them while they are in the open.”

Tramp, journalist, bull: for Willard, these had become mere roles to further his research and ­writing. The railroad gig had the added benefit of respectability, something Willard, oddly enough, had craved from his earliest days. As a boy, he had harbored vague dreams of going off somewhere, anywhere, and making a name for himself, becoming “well-to-do and respected,” then returning to his former friends as some sort of conquering hero. Despite his many adventures overseas, Willard felt he had squandered his youth in Europe. He bemoaned the “lackadaisical” habits he had acquired there, and envied the jump that his peers in America had gotten on him. Here was a chance, he thought, to catch up.

Europe, time, and drink, however, had softened him for the job. After a month of tramp life, Willard begged off, insisting the job would go smoother if he could ­simply ride the trains like any other passenger. After much discussion with Loree, a pass was issued, “good on any movable thing that [Loree] had on his property.” Over the next several months, Willard worked as an undercover operative and a ­patrolman, visiting jails, prisons, and workhouses, interviewing conductors and tramps. Frequent reports were made to Loree about tramp movements and activities: where they were stealing coal, what lines they were afraid to ride, what they felt about the efficacy of Loree’s police force. On one occasion, Willard fingered a career pickpocket, who gave him “the worst scolding I have ever had in my life”; on another, he was saved from a gang of toughs by “George the Fourth,” a razor-wielding hobo who unwittingly befriended him. All the while, Loree’s other officers wondered about the tiny snooping man among them, the one with the eager curiosity and full-ride pass.

One month into his tour, on a freight train traveling west of Mansfield, Ohio, Willard revealed just how far his loyalties had shifted away from his former colleagues. “I saw three tramping negroes on this train,” he wrote. “I saw them get on the train… and went after them, car after car full of coal, until I reached the biggest of the three.” After snatching the man’s hat, he ordered all three to jump off the train. “Cap,” the largest man said, “the train is going a little hard.” After some consideration, Willard told the men that they could all get off at the next stop—then telegraphed ahead so that an ­officer would be waiting there to arrest them. At the station, Willard continued to vex the three, stopping them from hopping another train, threatening to shoot them with the gun he didn’t have. “The negroes wanted to fight me,” he wrote. The three were given ­thirty-day sentences, and Willard—for no apparent reason other than pure vindictiveness—rode along with them to the local workhouse. “During that ride,” he wrote, “I heard all the hard things that can possibly be said about any one.

“This experience and my participation in it may not seem so very creditable to one who had himself been a tramp,” he added. “But what did I learn about those negroes? They had been employees of a circus, had got drunk and into a row, and had left their positions as circus men. So far as I have been able to make out, they had no right to have a free ride anywhere.”

Willard offers little explanation for this or other equally “uncreditable” actions in Notes of an Itinerant Policeman or in My Life, his posthumously published autobiography. There was, of course, the money: ten bucks a day to do what he had spent much of his life doing for free, plus the additional money he got for writing about it. And it’s not as if these were good people, Willard could tell himself; these were tramps, after all. Even when he was one of them, he felt that life on the Road was wrong, a waste, degraded and degrading.

Moral considerations aside, Willard also simply loved the excitement of police work. Once, while walking with a friend in New York, he wondered aloud, What would it be like to chase a man? “I know what it is like to be chased,” he said, “but to chase a man would be a new sensation.” A week later, he had been appointed a private detective. Bannister Merwin, Willard’s cousin, recalled times when Willard would pretend that strangers were pursuing him, just so “that he might enjoy to the full the sensation of being vainly hunted.” As an undercover lawman, Willard could savor the thrills of playing a hobo without the shame of actually being one. One of his prized possessions was a discharge certificate from his days working with U.S. marshals in Oklahoma. “He was very proud of the certificate,” wrote Merwin, “and took much pleasure in showing it to his friends.”

In eight years, from 1899 to 1907, Willard published five books and scores of magazine ­articles. Few besides his autobiography ­follow any sort of chronological pattern, jumping here and there in time, interweaving anecdotes and ­commentary. While reading a story about a particular hobo that ­Willard knew—Old Boston Mary, say, or ­Illinois Blackie—one will often come to the jarring realization that Willard was writing all of this while he was a reporter or a detective, not, as one first assumes, a fellow tramp. In many cases, it’s impossible to determine just what Willard was
doing, what role he was playing, as the story unfolds.


Today, Willard is all but forgotten. Though he was often dubbed the first muckraker,7 other, less conflicted individuals, ones who hadn’t ­ratted out their colleagues and blown their money and health on booze and cocaine, soon overtook him. Few read him nowadays; next to the muscular, vibrant prose of ­fellow tramp Jack London, Willard’s writing comes off as fussy, preachy. Symons wrote a short remembrance about the man’s life and ­final days, but the memorial, if it can be called such, feels more like he was gutting the man than paying tribute to him. Here was a man,
Symons noted, who had met Tolstoy and Ibsen, traveled the world, seen Tamerlane’s tomb, yet cared little for art or books or beauty. He was fond of family and friends, but could do without them, and often did.

In January of 1907, Willard, ­thirty-seven, contracted ­pneumonia. A heavy smoker from the age of nine, he had spent much of his adult life consuming prodigious amounts of alcohol and narcotics; that, coupled with a life spent on the Road, ultimately laid him low. He spoke ­often about his impending death and of what others might say about him after he passed, but not of an afterlife. “So-and-so will speak a good word for me, I know!” he told friends.

Willard was in Chicago when he fell ill, working on a story about pool gambling for ­Cosmopolitan. He hid out in his small hotel room, told his friends to keep his mother away so that she wouldn’t see him suffer, and refused medical ­treatment until he had become completely incapacitated. At seven p.m. on January 20, Willard died. “For three years,” wrote Symons, “he was rarely sober, and drink killed him. At the end he shut himself away in his room at the hotel in Chicago, as Dowson shut himself away in his lodgings in Featherstone Buildings, and ­Lionel ­Johnson in his rooms at Gray’s Inn;8 as a sick animal goes off into a lonely corner in the woods to die in.”

In the last chapter of his autobiography, Willard offers a rare explanation of why he tramped. For much of his life, Willard had described the lure of the Road as a troublesome, worrisome addiction, something to be struggled against. Here, finally, the author considers another possibility. Maybe tramping was fun, he posits, because hanging out with losers and lowlifes makes a man feel so much better about himself. Besides the vicarious pleasure of consorting with notorious characters and experiencing, at a safe distance, their wild adventures, one can bask in the ­knowledge that one’s own life is nowhere near as wretched as theirs. As much as Willard may have tramped, he was never, in his mind, a true tramp, and just being around them gave him a thrill of superiority that came none too often in his brief life. “Haven’t you, when a youngster, thrust your toes out ­under the blankets on a winter’s morning for the express purpose of accentuating the comfort of the bed when you drew them back again?” he wrote. “I guess you have. And so, I think, respectable people like to emphasize their respectability by bringing it into close, if temporary, contact with its antithesis. A shudderful joy results, no small part of which arises from the conviction that we are not like unto the other men.” 

1. London was likely being facetious here, but his dedication reveals his acknowledgment of Willard’s status as the “authentic” hobo of his day, even if that status was, to London, unearned.
2. Why Willard felt the need to dress up for his first day as a hobo goes unexplained.
3. Like Willard, Hodder wrote under a pseudo-nym: Francis Walton.
4. According to Willard, the job consisted primarily of shoveling and hauling large amounts of coal and hot ash.
5. To prepare for the trip, Willard consulted the sections on Switzerland in Mark Twain’s A Tramp Abroad.
6. Among his many other positions, Loree was president of the B & O Railroad, of Monopoly-
board fame.
7. Historian Louis Filler devoted two chapters of his 1939 book, The Muckrakers, to Willard, titled
Cigarette, and, appropriately enough, The First Muckraker.
8. Ernest Dowson, English poet, died of alcoholism at thirty-two; Lionel Johnson, British poet and critic, died at thirty-five after falling in the street—his own alcoholism had rendered his skull “thin as paper.”
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