Transcona’s Hidden Stills: How the CN Shops Sparked a Manitoba Bootlegging Empire
- Oct 6
- 9 min read
The Prohibition era is often associated with scenes of 1920s Chicago, of speakeasies and gangster drive-by shootouts with Tommy guns. No one would ever really think of the CN Transcona Shops as a part of that intense history of crime and bootlegging. In 1916, Winnipeg began its Prohibition era, and into the 1920s, it quietly operated an underworld enterprise. It was there, in the shops, among the soot-stained engines and industrial machinery, that Bill Wolchock, a young immigrant rail worker from Russia, would take his first steps into what would become one of Manitoba’s largest bootlegging operations, eventually branching into a sophisticated network that collaborated with the underworld bootlegging operations of the United States.
Manitoba had enacted prohibition on March 13, 1916, following a contentious referendum. Although intended to curb vice and uplift public morality, as seen in the United States' prohibition, it instead laid the groundwork for black market economies. According to his son, Leonard Wolchock, two CNR employees, including his father Bill, built a still within the massive Transcona railway shops to make liquor for themselves and their friends. The results exceeded expectations. As demand for alcohol surged during Prohibition, especially south of the border, so did Wolchock’s ambition. Leonard was interviewed by Bill Redekop for his book, "Crimes of the Century: Manitoba's Most Notorious True Crimes," which includes a chapter on Bill Wolchock's story. In the book, Leonard states, "Sonny (nickname), a CNR boilermaker, one day came up to my dad, who was a machinist with the railway, and asked if he could make a part for him. 'What's it for?' my dad asked. 'It's for a still,' Sonny said. Sonny was making stills for farmers out in the country. My dad said, 'Sonny, you want to make a still? I'll make you a still and we're not going to fool around!'"
“Before you know it, my dad was making big booze,” Leonard recalled. “He could knock out almost 1,000 gallons a day. He wasn’t one of these Mickey Mouse guys making 10 gallons like in the country.”
What started as a side hustle soon became a full-fledged business. Wolchock left the railway and began bootlegging full-time. He partnered with fellow workers and men who knew how to fix and haul loads. They weren’t criminals in the traditional sense; they were tradesmen looking for other methods of income, mainly due to the economic downturn after the First World War. Wolchock’s operation grew, and at its height, he oversaw multiple large stills across Winnipeg and rural Manitoba. One of the most infamous was a four-storey still operation on Logan Avenue, capable of producing hundreds of gallons of overproof alcohol daily. Another sat near the banks of the Red River on Taché Avenue, close to Provencher Bridge. Bill Wolchock would become the biggest bootlegger in Manitoba, and later, when the business was successful, he shipped almost exclusively to the United States, since Manitoba's Prohibition ended in 1923 and continued into the 1930s in the States.
Wolchock also used portable stills that could be moved from barn to barn across rural areas, from Tolstoi in the southeast to Reston in the southwest, making it nearly impossible for authorities to track him. His network included chemists, bakers, tinsmiths, drivers, farmers, and even bankers. His customers included American gangsters from Minneapolis, St. Paul, and Chicago. One of his runners once claimed they "stole a train" for Wolchock, according to his son Leonard, diverting a Canadian engine and three boxcars to load booze and switch it to the Soo Line headed to Chicago; this may sound far-fetched but the scale of Wolchock’s operation and the reputation he earned on both sides of the border suggest it is likely to be true.
Wolchock worked with regional suppliers to get around legal constraints. He arranged sugar shipments from bakeries and tinsmiths to produce gallon cans. He also worked with hog farmers to dispose of mash. A government liquor import store fronted the real operation. Even local garages were repurposed into 24/7 rumrunner depots. Unlike the mobsters and bootleggers of Chicago, Wolchock was not a gangster. He kept a low profile in the North End of Winnipeg, living at 409 Boyd Avenue with his wife Rose and their four sons. Despite his bootlegging, he established a reputation as a family man and respectful businessman. Local officials looked the other way or were on the payroll. The police chief, who lived five doors down, and the fire commissioner, who lived a street over, were both known to drop by the Wolchock residence for a drink.
“My father was a manufacturer,” Leonard said. “He was filling a niche market. I’m not ashamed of anything he did.”
While Wolchock was able to establish a successful operation, Al Capone was building an empire across the border. Capone is rumoured to have crossed into the Canadian prairies multiple times during Prohibition, including a visit to Winnipeg's Woodbine Hotel, where he may have enjoyed the looser enforcement and the comforts of speakeasies hidden in basements. It's very possible that Wolchock's shipments made their way into Capone's Chicago empire. Capone’s connections to Moose Jaw in particular are strong, where stories of him undergoing surgery, staying in secret underground quarters, and dealing with local suppliers who may have sourced their liquor from Manitoba. The Soo Line Railroad, which ran through the region, provided a discreet and efficient path for bootleggers to move product between Canadian producers and American syndicates.
Capone’s presence across the Prairies showcases his influence in a broader network of organized crime that stretched well beyond Chicago. Moose Jaw is known for its underground tunnels and hideaways, and over the years, it was rumoured to be used by Capone and his men to remain undetected by authorities and transport liquor. Residents of Moose Jaw and southern Saskatchewan shared accounts of Capone’s dealings with local doctors, barbers, and even clergy. Winnipeg was strategically positioned as a central rail hub with access to legal liquor markets during Prohibition. Warehouses, tunnels, and hotels became part of a much larger network that helped fuel Capone's empire from the Canadian side. As Capone tightened his grip on Chicago’s economy, the prairies ensured his supply lines.
Winnipeg’s geography and infrastructure also added to its appeal. The city had a long tradition of commerce and smuggling across the U.S. border through routes like the Turtle Mountains. Capone sent emissaries into the Prairie provinces to explore new trade routes, often dealing with men connected to both the Bronfman distilling empire and local producers like Wolchock. Some accounts suggest Capone’s men would arrive in nondescript cars and negotiate shipments, then vanish across the border before being noticed. Winnipeg’s conditions during the winter months also helped to keep smuggling under the radar. Capone was rumoured to interact with Canadian officials and police through bribes and under-the-table deals. In some Prairie towns, local law enforcement was believed to be part of the supply chain itself, ensuring that not too much red tape came in the way as barrels rolled across the plains, helping create an environment where cross-border trafficking was met with minimal disruption. Capone’s association with the Prairies shows just how vital this region was to the bootlegging trade.
Past accounts have rumoured that Capone's Cadillac was parked outside Prairie hotels, and the faint clink of bottles could be heard as they were smuggled through tunnels beneath the city. Some stories are subject to scrutiny, but they remind us that the Prairies were a significant part of North American organized crime.
Wolchock’s empire eventually collapsed under legal pressure. The legal proceedings against William Wolchock began in the summer of 1939, when he and numerous others were charged in connection with a large illicit liquor operation near Prairie Grove, Manitoba. The Crown alleged that the conspiracy defrauded the Dominion government of more than $100,000 in excise duties. The key witness was Howard Gimble, a bootlegger from St. Paul, Minnesota, who was already serving a penitentiary term. Gimble testified that he and two associates from Moorhead, Minnesota, came to Winnipeg in 1937 to establish a still and sought out Wolchock as a local partner to handle the distribution and provide financing. The still was first erected at the farm of Abraham Toews near St. Anne, later moved to David Lilkeman’s property near Steinbach, and finally set up at Paul Demark’s farm at Prairie Grove, where it was seized by the RCMP in April 1938. Gimble portrayed Wolchock as a financial backer and organizer who arranged sugar purchases under false names and introduced him to other contacts, including a Minneapolis bootlegger. Other witnesses, such as sugar wholesaler Max Kofsky, confirmed that Wolchock purchased large quantities of sugar under assumed names.
The Crown presented evidence from more than fifty witnesses, arguing that the conspiracy lasted from June 1937 to December 1938 and produced up to 20,000 gallons of spirits, defrauding the government of around $125,000. Crown counsel S. Hart Green described Wolchock as the “financial organizer and ringleader” of the entire scheme, while the defence insisted that his role had been overstated and did not amount to conspiracy. On March 21, 1940, after eight days of testimony and lengthy closing arguments, the jury found Wolchock and seven co-accused guilty on five counts of conspiracy. Wolchock was sentenced to five years in Stony Mountain penitentiary, plus concurrent two-year sentences on four additional counts. His co-accused received varied punishments.
Following sentencing, Wolchock filed notice of appeal, arguing that he was not part of the conspiracy, which had existed before his involvement, but was only guilty of participating in the still’s operation under the Excise Act. His lawyer claimed the jury had misconstrued and that the verdict went against the weight of evidence.
On June 27, 1940, the Manitoba Court of Appeal dismissed the appeal. The court upheld the convictions and sentences, ordering Wolchock to serve his full five-year term. With appeals exhausted, the case of the Prairie Grove still came to a close. The Wolchock case was one of Manitoba’s most significant bootlegging prosecutions of the prewar era. It exposed the scale of cross-border liquor operations in the late 1930s and concluded with the courts affirming Wolchock’s role as the financial ringleader.
Wolchock’s sentence was the harshest liquor-related sentence in Manitoba’s history. But even after serving his time, he never lost the respect of those who worked with him. He gifted former associates with money to start new lives: some opened liquor stores, others started businesses, supported his family and donated to charities like the Salvation Army. Leonard described the final operation, a last hurrah behind a false wall in the basement of the family’s North Kildonan home, as a farewell toast to the Prohibition era.
Bill Wolchock's story, starting from the CNR shops in Transcona, offers a unique view of the bootlegging narrative. In the vast, windswept plains of Manitoba, behind snowbanks and steel rails, a network of working-class ingenuity quietly supported one of the most notorious eras in North American history. And while Al Capone became a household name, it was men like Wolchock outfitting stills in the shadows and outsmarting lawmen who ensured the empire never went dry.
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