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Rum-runners — the “flying bootlegger” made booze flights from Winnipeg to Minneapolis to Chicago
Oct 09, 2014

by Bruce Cherney (part 6 of 6)
The “Roaring Twenties” was a period when the automobile was coming into vogue as a means of personal transportation — vehicles, such as the Model-T, were becoming more affordable to many would-be motorists — which translated into a steep increase in cross-border trips. And when it came to automobile tourism, the border was particularly porous, since cars carrying liquor could cross at any of the multitude of rural back roads connecting Manitoba to the U.S., which made police regulation of such entry points virtually impossible. 
“The dream of total abstinence was an utopia. An effective prohibition of alcohol was impossible  ... It’s unrealizable for the (U.S.) Custom Service and the Border Patrol to seal the several thousand miles long border with Mexico and Canada,” wrote Daniel Schmidli in his research paper, Prohibition and its Effects. 
The greater potential to attract tourism dollars had increased so significantly that Winnipeg was advertised in the U.S. Midwest as “the city of snowballs and highballs” in order to lure liquor-craving Americans north to the Canadian prairie city.
Illicit rum-running from Manitoba to the U.S. continued until the repeal of prohibition in the U.S., but never at the same intensity as witnessed in the early-1920s. Afterward, most of the rum-running from Canada to the U.S. had shifted to the Atlantic provinces, the West Coast and the Great Lakes Region, where great quantities of booze could be smuggled using all manner of transportation, including cars, trucks, row boats, speedboats and ships.
Especially important was the rum-running between Windsor, Ontario, and the U.S. The distilleries and breweries in the Canadian city and nearby Walkerville were able to supply a top-quality product to thirsty Americans. It was estimated in 1928 that rum-running on the Detroit River between Windsor and Detroit alone was worth $50 million a year, with only five per cent of liquor shipments smuggled into the U.S. from Canada seized by American law enforcement agencies. Five per cent is the usual figure given for seizures by American authorities across the length of the Canadian-U.S. border, which means that 95 per cent of the illegal liquor was getting through.
But rum-running across the Manitoba-U.S. border never abruptly stopped after the early-1920s. The March 7, 1932, Winnipeg Tribune reported that cars were “often stolen to run a cargo of booze across the border. Recently a car stolen from a parking place on Portage Ave. was found in a ditch not many miles south of the international line. It had been wrecked. The inside was smothered with broken bottles and there were stains of liquor and blood on the cushions. Evidently the bootleggers had been chased and overturned but there was no trace of who they were or where they had gone with their injured companion.”
Another car was stolen in the city and found abandoned on the Emerson highway, about 15 miles south of Winnipeg, after it had run out of gas on the return trip from the American side of the border. Evidence found in the vehicle confirmed that it had been used to transport liquor to the U.S.
One of the more high-spirited booze smuggling schemes involved the use of an airplane flown out of the edges of Stevenson Field (now Richardson International Airport) and Assiniboine Golf Course. Under the cover of darkness, several flights were made from Winnipeg to Minneapolis and then to Chicago by pilot James Michel, who was dubbed the “flying bootlegger” in a January 27, 1930, Tribune article.
 The actions of pilot were first brought to the attention of Canadian customs officials in October when residents of Linwood Street reported the drone of an airplane late in the evening and the sound of a high-powered auto racing down the road.
For weeks, customs officials staked out the area around the airfield, “and one night the plane passed over their heads. A few nights later they saw the plane on the far edge of Stevenson’s Field. They went after it, but were too late. They had seen a big automobile draw up and its load transferred to the plane. The car then sped off at 70 miles an hour. The plane soared away in safety.”
Frank Currie, of the Winnipeg Flying Club, said the silver monoplane in question would land at almost any convenient location without the benefit of guiding lights. He called the pilot of the airplane a “dare devil.”
Michel was identified to Canadian customs officials as the “flying bootlegger” after receiving a dispatch from the Chicago police, who raided his apartment, where they found the names of approximately 2,000 persons in a card index, many of them leaders in the Chicago’s social and political life.
“Officers (of the Chicago police) charge him with flying liquor from Winnipeg to Minneapolis and then to Chicago for sale to wealthy buyers. The raiders (of his Chicago apartment) found 14 cases of what they allege to be genuine Canadian whiskey and 22 suits of tailored clothes which pointed to a brisk trade.” 
Michel eluded capture in Manitoba. A warrant for his arrest had to be issued after the “flying bootlegger” flew the coop. 
American customs officials commented that using airplanes to smuggle booze to the U.S. was prevalent in Eastern Canada, but this was the first incident reported in Manitoba. They said “that although the border is well patrolled for motor cars rum running by the plane is a more difficult problem to handle.”
In fact, it wasn’t the first such incident, as a plane filled with legally purchased commission liquor destined for the U.S. was seized at Waugh, Manitoba, a couple of years earlier.
In order to stop liquor smuggling, many in the U.S. said lessons could be learned by the Canadian example of provincial control over liquor sales.
“How long could the bootleggers last in this country, if liquor drinkers could buy at a government store honest whisky ... at no fantastic price,” claimed an editorial in the New York Tribune.
Actually, provincial governments, including Manitoba’s, learned well before the Americans in 1923 that the question of “wet” vs. “dry” was in reality a financial matter, rather than one involving some impossible to attain societal benefit. And being a “wet” province had a distinct advantage — Manitoba could reap the profits of the liquor trade at the expense of bootleggers, as well as obtain licence fees from the hotels and clubs allowed to sell beer by the bottle (beer sold by the glass was made legal in 1928). Government-run stores also had a monopoly on the sale of hard liquor, which by law could only be consumed in private homes. 
Government profits from liquor sales were diverted into better roads, education, health care and other social programs to benefit the province’s citizens. 
In addition, by answering the financial question through the implementation of government liquor control, the social issue of a rampant upswing in crime brought about by prohibition was, for the most part, also removed from the provincial law enforcement agenda. Formerly good citizens turned into criminals by ill-conceived social engineering were given the opportunity to return to the ranks of good citizens with the enactment of laws designed to regulate — not ban — alcohol consumption. 
Provincial governments across Canada came to the realization that promoting moderation was a wiser course of action than their failed attempts to go completely “dry.”
“We realized that we could not banish liquor by legislation,” said Manitoba Attorney-General W.J. Major in the legislature (December 8, 1927, Winnipeg Free Press). “We realized that we could not compel our people to break away from a habit — and a habit it is, and nothing more. Abuses which did not previously exist at any extent developed.”
With the Manitoba government enacting new liquor control laws in 1923 and then in 1928, the crisis at home brought about by local prohibition was resolved to its satisfaction, and it came to the conclusion that rum-running across the border was solely an American problem.  Or, at least, an issue that had to be sorted out at the federal level between the Canadian and U.S. governments. But with the Canadian government earning its own excise profits from the export of liquor, Ottawa was a very reluctant partner with Washington when it came down to negotiating the curtailment of the cross-border booze trade that was prohibited only in the U.S.  
Furthermore, the Manitoba government was only really interested in maintaining its monopoly on the importation and sale of liquor in the province, and on this front, the situation was made somewhat chaotic due to the proliferation of “blind pigs” and local bootleggers operating in the city. 
Manitoba Provincial Police (MPP) were solely responsible for the enforcement of the Manitoba Temperance Act in order to stop the illegal sale of booze from private dwellings across Manitoba. But Winnipeg police department’s morality squad did engage in enforcement of the provisions of the act. Stretched to the limit of its resources, the city police and Mayor Ralph Humphreys Webb were assured by Premier John Bracken that they would receive help from the MPP when needed. Further help came in the form of funding for the city’s morality squad by the province for their assistance in enforcing the act, which in 1927 was $30,000.
Winnipeg Mayor Ralph Humphreys Webb declared that for every hotel and club legally selling beer there were hundreds of “blind pigs” located in houses, apartments, business blocks and boarding houses selling whiskey illegally in the city (Winnipeg Free Press, January 15, 1927). At the time, Manitobans could only legally purchase hard liquor from government stores for consumption in their homes. But in some instances, people were unable to buy legal liquor because the government stores were closed when they finished work, so they went to the blind pigs to slake their thirst.
“There is a large illicit liquor trade in Winnipeg,” reported the Tribune on November 10, 1930, “and it would be much larger if it was not kept in check by the boys of the morality squad.”
Homebrew peddlers were said to be operating in the “poorer” areas of the city.
“Poor people who can’t afford legal liquor can buy (a) ‘pop’ bottle of home-brew for 50 cents. This usually runs about 150 per cent proof spirits, which is nearly four times stronger than ordinary whiskey or gin.”
The production of homebrew was primarily confined to the outskirts of the city. “The morality squad cannot attempt to stop the flood at its point of origin, so they confine themselves to catching the wholesalers, jobbers (middlemen) and retailers.
“It is well known there is a big bootleg liquor ring which supplies not only Winnipeg but most of the territory for many miles around. Occasionally officers of the customs excise branch, with aid of the Royal Mounted police, will seize a still which is operated by the ring. The men caught operating the still, usually farmers and laborers, are hardly in jail before some high-priced lawyer is retained on their behalf. They are soon out on bail and if they are convicted and fined the money is ready.”
When convicted, the bootleggers faced stiff fines and even imprisonment for as many as two years. Local newspapers were filled with bootlegging cases before the courts and the fines and penalties levied, an indication of the extent of the problem the province faced in attempting to maintain its liquor sales monopoly.
As for the U.S., it also became quite evident that prohibition wasn’t working. In fact, abuse of alcohol increased dramatically. The solution had become worse than the problem. And as in Canada, prohibition was an economic disaster. Besides the upswing in gangland crime, the transformation of millions of former honest citizens into criminals and widespread corruption of government and law enforcement officials, states lost excise tax revenue that couldn’t easily be replace. Prohibition cost the federal government a total of $11 billion in lost tax revenue, while costing over $300 million to enforce. 
What to do? 
States and the U.S. government became more reliant on income taxes to the chagrin of Americans.
It wasn’t until March 1933 that prohibition was repealed — the U.S. Congress voted 93 per cent for repeal — and booze flowed legally for the first time since the 18th Amendment became the law of the land in January 1920. With the repeal of U.S. prohibition, the heyday of cross-border rum-running in all its variations came to an abrupt end.