No fixed address: The history of hoboes in Ontario

For decades, transients took to the roads and the rails, hopping freight cars, establishing hobo jungles — and risking death at every junction
By Lorna Poplak - Published on Aug 17, 2021
Tramps travelling in a freight car pass the time playing cards, ca. 1910. (Everett Collection)

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On March 20, 1899, William Henry Davies stood waiting for a train in the snow-covered town of Renfrew. Davies, an 18-year-old from Wales, was on his way across Canada looking to find fame and fortune in the newly discovered gold mines of the Klondike. His travelling companion, Three Fingered Jack, was a cattleman from Montreal who had earned the moniker after losing two fingers of his right hand in a work accident. The duo had no funds, nor did they have any intention of buying a ticket for the fast passenger train just steaming into the station. Their plan was to hitch a ride on the platform of one of its baggage cars. Despite his youth, Davies was no novice; he had already spent a couple of years crisscrossing the United States and Canada atop, beneath, hanging from the sides of, or, ideally, inside railroad cars.

man with a bindle
Itinerant worker, 1938. (Dorothea Lange, Everett Collection) 

With a whistle, the train chugged slowly out of the station, and the two darted across to clamber aboard. The train picked up speed, forcing them to run alongside. “I allowed my companion the advantage of being the first to jump, owing to his maimed hand,” Davies later wrote. But instead of moving immediately off the step onto the platform of the car, Three Fingered Jack just stood there, “thoughtlessly irresolute.” By the time Jack had made room for Davies, it was too late: Davies missed his footing. Desperately holding onto the handrail as the locomotive accelerated, he was dragged several yards before he let go. Shaken, confused, and not able to stand, he “found that the right foot was severed from the ankle.” After five weeks and two painful surgeries — the second to amputate his leg at the knee — Davies returned to England. His train-hopping days as a self-styled super-tramp were over.

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Etymologists distinguish three separate categories of migrants who took to the roads and rails of the U.S. and Canada from the 1890s onward — hoboes (or hobos), tramps, and bums. According to the University of Minnesota’s Anatoly Liberman, “Hobos worked, tramps worked only when made to, while bums did not work at all (quite a hierarchy).”

In his memoirs, Ronald Liversedge, an Englishman who met up with hundreds of jobless workers after his emigration to Canada in 1927, paints a vivid picture of “the life of the transient unemployed,” writing, “I learned of freight riding, of life in the [hobo] jungles, cooking mulligan stew with a chunk of bummed meat, and stolen potatoes; of arrests for vagrancy and thirty-day prison sentences; of being hounded by police from town to town.”

headline about "lady hoboes"
Headline from the August 8, 1934, edition of
the Globe and Mail.

Typically, hoboes or migratory workers were young single men — but not all of them were. In August 1934, the Globe reported that two “lady hoboes” were among a party of five Hungarian immigrants found hitching a ride in a box car on their way to work the tobacco fields at Delhi, in southwestern Ontario. Children, too, rode the rails. In December 1935, Charles Reid, a penniless veteran of the First World War, took his six-year-old daughter, Dorothy, on a cross-Canada trip from Lambton Mills, Toronto, to his parents’ home in Edmonton. The Globe described the girl as “bright-eyed and laughing” when she and her father jumped out of a box car on arriving at their destination.

The insouciance of Ontario’s (possibly) littlest hobo should not detract from the risks involved in stealing a ride. Hoboes faced hostility and violence from train crews. Brutal railroad police or “bulls” had no compunction about arresting or beating up non-paying customers. And the danger of being maimed or killed in an accident was ever present. In 1908, Walter Chambers, a hobo riding on the bumpers of a Grand Trunk freight train near Toronto, had his foot crushed when he slipped between two cars. In February 1949, Frank Gosse and Jimmy Wiltshire attempted to board a fast-moving train at the Scarborough Junction railway yards. Wiltshire missed his step and was flung against the moving cars, suffering cuts and bruises. Scarborough police later found Gosse’s mangled body along the tracks some 200 yards from where the two men had tried to climb onto the train.

One of the most notorious train hoppers in Ontario was Leonard “Tough Lennie” Jackson. In

woman holding on to the side of a train
Female hobo climbing freight train. (Everett Collection)

1946, bored and restless after his discharge from the army at the end of the Second World War, Jackson took to the rails. He was no greenhorn, having ridden the rails as a youth. But an attempt to jump aboard a freight train in Toronto ended in disaster. His left foot was severed, and his leg had to be amputated just above the ankle. Jackson went on to become a core member of the Boyd Gang, a band of bank robbers who alternately terrified and enthralled the Canadian public in the early 1950s. 

The situation of hoboes, always tenuous, reached its nadir in the 1930s, when the swell of transients in North America became a tidal wave. On Black Tuesday, October 29, 1929, the New York stock market crashed, plunging the world, and Canada in particular, into the catastrophic Great Depression. By 1933, the unemployment rate in Canada stood at around 30 per cent. There was no national unemployment-assistance program, and local governments generally refused to come to the aid of single, homeless men.

Historian Jennifer Bonnell, who has documented the history of homelessness in Toronto’s Lower Don River Valley, writes that, in the early 1930s, an army of unemployed men set up a “hobo jungle” in the flats just north of Bloor Street. In June 1931, a headline in the Toronto Daily Star revealed that “300 Jobless Sleep Nightly Along Don River’s Banks”; a few months later, the number had grown to around 400. The valley, which was close to the city centre and had a ready supply of water, as well as discarded items that could be used in building makeshift homes, was also cut through by rail lines. True Davidson, a former mayor of East York, wrote in her 1976 memoir that “the jungle became known amongst the fraternity” of people riding the rails, and “almost every freight that came down the Don brought more inhabitants to the area.”

black and white photo of a homemade shelter
 Makeshift shelter on the Don flats, ca.1931. (City of Toronto Archives, Fonds 592, Series 2604; X973.151.6)

The existence of this sanctuary, notes Bonnell, was short-lived. Despite the deepening Depression, authorities in Toronto and East York stated that winter relief services would be denied to outsiders; the police, as indicated in a Globe headline in September 1931, started to “Watch Every Freight Train for Jobless Influx”; by October, the temporary dwellings in the jungle had been demolished.

As social historian Wayne Roberts notes, these hobo jungles had a subculture all their own. Some of the residents would go out “stemming” or panhandling, often in exchange for work. Others would target bakeries or stores for leftover food that they would bring back to the jungle to be cooked by a hobo chef. Reportedly, hoboes would scratch graffiti on houses or walls to alert their fellows to local conditions, such as a kindly homeowner or a barking dog. And they certainly had an ethical code, which was established at a National Hobo Convention in St. Louis, Missouri, in 1889. As riding the rails knew no borders, this code was most likely known to hoboes in Canada as well. Some examples: Decide your own life; don’t let another person run or rule you. Always respect nature; do not leave garbage where you are jungling. Do not allow other hoboes to molest children.

The Second World War brought significant changes. The army of young and jobless enlisted, joining a different army to fight for a system that had historically offered them so little support. When the federal government introduced unemployment insurance and family allowances during the war and full employment after the war, a safety net was finally put into place. What Liversedge called “private enterprise at its most brutal period” came to an end. The hobo army began to melt away.

left: photo of man with cap and pipe; right: mug shot of short-haired man
Left: William Henry Davies in 1913. (Alvin Langdon Coburn); Right: Mug shot of Lennie Jackson from the September 9, 1952, edition of the Globe and Mail.

William Henry Davies was profoundly affected by the accident in 1899 that cut short his life as a rover and left him a “one-legged” man. “All the wildness had been taken out of me,” he wrote in his Autobiography of a Super-Tramp. Some 50 years later, Lennie Jackson suffered an equally crushing injury and, like Davies, ended up with an artificial limb. But that’s where the similarities cease. Davies went on to become one of the most famous British poets of his generation; Jackson became a bank robber. Two years before his death in 1940, Davies suffered a stroke. According to his biographer Richard Stonesifer, “The weight of his wooden leg and the hardships of his youth had finally undermined his rugged health.”

As for Jackson, after being arrested for a series of violent crimes, he famously secreted several saws in his prosthetic leg to help him and his fellow Boyd Gang members escape from Toronto’s Don Jail in 1951. After a second jailbreak and recapture, he was hanged at the Don Jail in 1952 for the murder of a Toronto policeman.

Sources: The Autobiography of a Super-Tramp by William H. Davies (Alfred A. Knopf, 1917);“Canada’s hoboes: a generation of radicals” by Wayne Roberts (Globe and Mail, Nov 5, 1984); Edwin Alonzo Boyd: The Story of the Notorious Boyd Gang by Brian Vallée (Doubleday Canada, 1997; The Globe editions of July 16, 1908; August 8, 1934; and December 31, 1935; the Globe and Mail edition of February 21, 1949; “The Great Depression” (Maclean’s July 1, 1999); “Hobo Code” (Hobo News, hobo.net); “Jobless Army” (cbc.ca/history); “On Hobos, Hautboys, and Other Beaus” by Anatoly Liberman (The Oxford Etymologist, blog.oup.com, 2008); Recollections of the On to Ottawa Trek by Ronald Liversedge (McClelland and Stewart, 1973); Toronto’s Underworld: The Don River Valley as a “Repository for Undesirables” by Jennifer Bonnell (Presentation to the Canadian Historical Association Annual Meeting, Vancouver, British Columbia, 2008); W.H. Davies: A Critical Biography by Richard J. Stonesifer (Jonathan Cape, 1963).

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