The King Beneath the Streets:

Christopher “Shorty” Young and the Lawless Empire of Havre, Montana

Introduction: A Town Built for Vice

In the long arc of Montana’s frontier history, few figures occupy as singular a position as Christopher William Young, known to nearly everyone as “Shorty.” The north-central Montana railroad town of Havre, perched along the Hi-Line roughly equidistant between Minneapolis-St. Paul and Seattle, served as both Young’s stage and his kingdom for several decades straddling the turn of the twentieth century. From its beginnings as a railroad town in 1887, Havre was a tough town with plenty of saloons, gambling halls, opium dens, and brothels. With the passage of Prohibition, it was a natural hub for smuggling illegal alcohol across the nearby Canadian border.  Into this environment came Shorty Young, whose career as a saloon keeper, brothel operator, bootlegger, and political operator made him one of the most consequential — and controversial — figures in the history of northern Montana.

Young’s story is not merely one of personal ambition; it is inseparable from the broader history of an era defined by rapid industrialization, mass migration to the frontier West, the tensions between reformers and vice operators, and the peculiar geography of the northern Hi-Line, where the border with Canada was long, lightly policed, and financially irresistible to those willing to exploit it. To understand Shorty Young is to understand, in miniature, how American frontier towns were shaped as much by their criminal economies as by their churches, schools, and railroads.

Origins and the Road to Havre

The precise circumstances of Young’s early life remain somewhat obscure, as was common for men who lived by the unspoken frontier code of asking no questions and answering even fewer. At the age of thirteen, Shorty went to Canada. He was employed by a friend of the family who perhaps acted as a guardian. The benefactor was in the insurance business and also owned a racetrack. Here Shorty learned to handle racing horses. For whatever reason, Young left New York in his early twenties and landed in Duluth, Minnesota. Shorty said he only made enough money in Duluth to go farther west. His next stop was Fargo, North Dakota. Fargo had several combination liquor and entertainment establishments. They featured all-night vaudeville acts and girlie shows such as Shorty’s future Honky-Tonk. By the time he reached Havre, he was an expert in all games of chance.



Shorty was “Shorty” because he was only about 5 feet 2 inches. But he was well proportioned and wiry, almost as if he were a wrestler or an acrobat. The blue-eyed, brown-haired Young always had a big cigar in his mouth. He generally wore suits and loved striped shirts. He came to Havre in 1895 and first worked as roulette wheel operator at Decker’s Palace Hotel on First Street. Shorty’s first call was at Reuben Hauser’s barbershop. Without funds he received a haircut and shave on the cuff. He then registered at the Windsor Hotel, changed clothes, and headed for the gambling houses. After a few hours at the tables, he made enough to reimburse Hauser, pay the hotel, and keep pocket money too. In keeping with the code of the West, Shorty spoke little of his past and no one asked.



This arrival story, compact and almost mythic in its structure, captures the essential character of the man: resourceful, self-possessed, and already skilled enough at cards and chance to transform a penniless entry into a financial foothold within hours. Young’s ability to read opportunity and act on it quickly became the defining trait of his long and eventful career.

Building an Empire: The Honky-Tonk and the Mint

Young’s ascent from roulette wheel operator to proprietor of northern Montana’s most notorious entertainment complex was rapid. Shorty probably would have always remained just a colorful saloon dealer except for one thing: He introduced a new game to Havre called Chuck-a-Luck (or Hazard). The new toy took Havre by storm and Shorty cleaned up. With his newly found wealth, he soon bought the Havre Beer Hall from his old boss Mayor Eugene Shelton. 

The centerpiece of Young’s empire, however, was the establishment he raised in 1898 on the west end of Havre’s First Street. The three-story frame building, the largest in northern Montana, was officially named The Montana European Hotel and Grill. But it was known as the Montana Concert Hall or just plain Honky-Tonk. It employed 28 people not including the girls. The main floor of the Honky-Tonk contained a raised stage on one end with about 30 tables in front of it. An open space between the stage and tables was used for any musical accompaniment. On stage vaudeville acts performed nightly for the audience while girls circulated in gaudy low-cut evening dresses and hawked drinks. 

The Montana European Hotel and Grill was far more than a saloon. It was a vertical ecosystem of frontier entertainment: vaudeville on the stage, alcohol at every table, gambling in the back rooms, and prostitution available for those who sought it. Its scale distinguished it from nearly every competing establishment in the region. His notoriety spread throughout the West. Very few salesmen or drummers would miss an opportunity to stay at Shorty’s Montana Hotel. 

Young did not stop at the Honky-Tonk. Soon after the Honky-Tonk opened, Shorty built another bar in the Pepin-Broadwater block. He called it the Mint. It was strictly first class: a bar with woodwork of mahogany, marble-topped tables, and inch-thick linoleum. The basement housed a restaurant. It had private booths with fancy opaque glass windows in the doors. The drinks were served in genuine cut glass. Around the bar on a shelf just below the ceiling were mounted animal trophies of all types, including mountain sheep, eagles, and alligators. 

The contrast between the rough Honky-Tonk and the upscale Mint reflected Young’s business acumen. He understood that different customers required different environments, and he built accordingly. His holdings eventually extended well beyond saloons and entertainment. With his saloon businesses booming, Shorty soon became a very rich man. He bought property in downtown Havre at the east end. Among his holdings was a 6,000-acre ranch on the hill west of town. The ranch had 600 head of livestock and a large coal mine. 

The Underground: Fire, Adaptation, and Subterranean Commerce

The catastrophe that reshaped Havre’s physical landscape — and extended Young’s influence into an entirely new dimension — came in January of 1904. In January 1904 several of those drunken men set fire to one of those wooden buildings — supposedly a saloon that had kicked them out — and the flames spread. Within a few hours most of downtown Havre was a smoldering ruin. Havre’s citizens, however, did not abandon it. The city rebuilt itself in nonflammable brick while its businesses — respectable and illicit — stayed open in a tunnel-connected network of underground rooms. 

Young was central to the construction and operation of this subterranean network. Others of an entrepreneurial bent decided to forgo the costs of constructing new buildings. Instead, they moved their businesses under the city streets into a mixture of steam tunnels and passages made by Havre’s famous gangster mayor Shorty Young to facilitate passage between his businesses.  Young’s tunnels ran not merely as shared commercial passageways, but as private arteries connecting his own properties. Shorty built his own set of tunnels that ran among only his own buildings. He also had an escape tunnel that began under the stage and went several hundred yards to the west, surfacing in a dumping ground. 

Young’s underground office became a physical symbol of his dominance over the subterranean commercial world. Shorty Young was quite an entrepreneur in Havre and had some pretty spiffy digs under the streets. Notice the nice chandeliers, large wooden desk and of course, a couple of decanters.  The underground space, now partially reconstructed as the tourist attraction Havre Beneath the Streets, still preserves a recreation of Young’s office, complete with a mannequin of the man himself — cigar in hand, shotgun within reach, accounts ledger on the desk. It is an image that condenses an entire era of frontier capitalism into a single tableau.

A 1916 report by the Law and Order League of Chicago, which surveyed 28 American cities for comparative lawlessness, concluded that Havre was among the worst it had encountered, describing the Hi-Line town as “the sum total of all that is vicious and depraved parading openly without restraint.”  That Havre earned this distinction during the peak of Young’s influence is unlikely to be coincidental.

Prohibition, the Border, and the Bootlegging Empire

Montana adopted statewide Prohibition ahead of the national Volstead Act. The federal Volstead Act, better known as Prohibition, was ratified in January of 1919. Given Havre’s close proximity to Canada and the thin population along the Hi-Line, liquor smuggling and bootlegging became a profitable business for some locals. In Havre, Prohibition meant the closure or modification of many saloons.  For Shorty Young, already rich and experienced in managing operations that skirted or defied legal authority, Prohibition was less a disruption than an upgrade. The same infrastructure — the tunnels, the Border Saloon near the Canadian line, the network of trusted associates — that had served him in the pre-Prohibition era could be repurposed for smuggling at a dramatically higher profit margin.

In Havre, Christopher William “Shorty” Young maintained a bootlegging empire near the Canadian border, propped up by his dens of sin known as the Mint and the Montana European Hotel and Grill.  The geography was ideal. The Montana-Canada border stretched for hundreds of miles with minimal federal enforcement presence, and Canadian distilleries continued legal production throughout America’s dry years. Because alcohol production was legal in Canada when it was illegal in America and due to Montana’s easy access to the neighboring country with a border that was lightly guarded at best, moonshine and other illegal alcohol was able to make its way into the state and beyond. 

Young’s operation was not merely local; it was regional in scale, and it made him one of the most prominent bootleggers along the entire northern border. It was during this era of depression, drought, and violence, that successful businessman and philanthropist C.W. “Shorty” Young rose to power as the leader of the organized crime element. His Montana Hotel — known as the “Honky Tonk” — catered to all man’s carnal desires, gaining notoriety throughout Montana and as far as Seattle and St. Paul. 

Resisting Authority: The Border Saloon Raid of 1918

Young’s determination to resist legal interference with his businesses was not passive. He actively fought local, state, and federal authorities with a combination of legal maneuvering, political connections, and what can only be described as institutional cunning. The failed border saloon raid of 1918 stands as one of the clearest illustrations of his ability to outmaneuver his opponents.

In the October 5, 1918 edition of The Havre Plaindealer, a headline ran “Sensational Story Is Badly Exploded — Disagreeable Features in Border Raid Case, Miserable Fizzle Disgusts Intelligent Citizens of County” with a lengthy account of what the Plaindealer could find out about the raid of a saloon located near the Canadian border. The raid involved an assistant in the state Attorney General’s office, Grorud, and some local men he was either working with or who were forced to work with him. 

The aftermath revealed the extent to which the raid had been legally compromised from the outset. The Attorney General’s Office conducted its own investigation, finding that its own deputy, Grorud, had conducted an “improper and illegal” raid along with illegally deputizing two men as deputy sheriffs, arming them and ordering them to “shoot to kill” anyone who interfered with the raid. As a consequence, Grorud and the two men were arrested. 

The owner of the Border Saloon? Christopher William Young — also known as “Shorty.” Who, in turn, quickly reclaimed his loot and by the time a proper warrant to search the site was made and officials arrived, “They secured as evidence a one-quart beer bottle, containing about three drinks of whiskey.”  The outcome was almost farcical: a state-sponsored raid, conducted by illegally deputized men, resulted in the arrest of the raiders themselves, while the intended target walked away having recovered his property. Whether local, state, or federal government, Shorty fought them all — and usually won. 

The political dimensions of the 1918 raid were also instructive. C. R. Stranahan was also leading a revolt of local Republicans, splitting the party into two factions. The Plaindealer called out that the whole raid was an effort on Stranahan’s part to bolster his campaign, which ultimately failed on technical grounds.  Young’s ability to make use of political rivalries and factional disputes — to position himself as a victim of political opportunism rather than a lawbreaker — was a recurring feature of his long tenure.

Legacy, Heritage, and Historical Significance

The full arc of Young’s life and career spans one of the most turbulent and transformative periods in Montana’s history: the arrival of the railroad, the mass settlement of the Hi-Line, the drought and agricultural collapse of the 1920s, the long struggle over Prohibition, and the gradual — if never quite complete — reformation of Havre’s civic character. Wilson’s book delves deep into those 50 years when Havre was a major outpost of boozing, partying, and general mischief. The accounts of the bootlegging operations between Havre and the Canadian border are extensive. 

Young’s physical legacy endures in the underground passages that still run beneath First Street. Havre’s underground flourished until around the 1920s and 30s, when the town endeavored to straighten out and go legitimate. The tunnels gradually fell out of use, filling with rubble and detritus until Frank DeRosa and Lyle Watson had the tunnels excavated and restored. They opened Havre Beneath the Streets, which offers tours of the tunnels complete with historical reconstructions of the opium den, saloon, and restaurant.  Havre is also growing in popularity as a major cultural tourism destination. One of the city’s most important attractions is Havre Beneath the Streets, a collection of exhibits in block-long tunnels located under the city. These passageways were originally created after the Fire of 1904 wiped out most of Havre’s business district, and many businesses moved underground while they rebuilt. 

A mannequin of Christopher “Shorty” Young, the town bootlegger and brothel-owner, sits at his desk tabulating his profits, a shotgun at arm’s reach and fake smoke curling from the end of his cigar.  The image is simultaneously humorous and sobering: a permanent monument to a man whose enterprise, whatever its moral dimensions, was inseparable from the economic and cultural life of a frontier town that needed someone like him, even as it occasionally tried to put him in jail.

Young’s career raises questions that extend well beyond the particulars of Havre’s history. In many frontier towns, the vice economy was not merely tolerated but was actively integrated into the formal economy: saloon owners paid taxes, employed workers, attracted travelers, and circulated money that sustained legitimate businesses. Young’s 6,000-acre ranch and coal mine, his real estate holdings, his luxuriously appointed Mint Bar — all of these represented genuine capital accumulation that had measurable effects on the local economy. At the same time, the prostitution and opium dens that operated under his roof represented real human suffering that deserves acknowledgment alongside any assessment of his commercial achievements.

Historian Gary A. Wilson, who has devoted considerable scholarly attention to Young and Havre’s lawless era, frames Young’s significance in terms that are both specific and broadly applicable: Honky-Tonk Town is also a microcosmic study of conflict over social norms. Wilson writes that “the old-fashioned virtues of the homesteaders and rural people were pitted against the ‘evil’ city dwellers” — a tension that defined the prohibition question in Havre during 1918.  Young embodied the city-dweller side of that equation: pragmatic, profit-oriented, cosmopolitan in his tastes, and deeply resistant to the moral legislation that rural reformers sought to impose on communities they did not live in.

Conclusion: The Measure of a Frontier Operator

Christopher “Shorty” Young of Havre, Montana, defies easy categorization. He was, at various moments, a saloon keeper, entertainer, brothel owner, bootlegger, rancher, real estate developer, and political operator. He built the largest frame building in northern Montana, constructed his own tunnel network beneath a city street, resisted the combined authority of local, state, and federal law enforcement for decades, and accumulated sufficient wealth to own a cattle ranch and a coal mine — all from an initial investment of nothing more than skill at cards and an instinct for opportunity.

His story is part of a larger and underexamined chapter in the history of the American West: the history of those who built the informal economy that sustained frontier towns while the formal economy was still finding its footing. The tunnels he dug beneath Havre’s streets survive him. The recreation of his underground office, complete with its chandeliers and decanters, draws thousands of visitors a year. And the debates his career embodies — about the proper limits of law, the economics of vice, and the complicated relationship between social order and human appetite — remain as alive today as they were on the Hi-Line a century ago.

Works Cited

Advisory Council on Historic Preservation. “Havre, Montana.” Advisory Council on Historic Preservation, www.achp.gov/preserve-america/community/havre-montana. Accessed 11 Mar. 2026.

Havre Daily News. “Celebrating History: Raid on Shorty Young Saloon a Debacle.” Havre Daily News, 12 Oct. 2018, www.havredailynews.com/story/2018/10/12/local/celebrating-history-raid-on-shorty-young-saloon-a-debacle/520836.html. Accessed 11 Mar. 2026.

Havre Hill County Preservation Alliance. “Historic and Architecturally Significant Resources of Downtown Havre, Montana, 1889-1959.” National Register of Historic Places Continuation Sheet, United States Department of the Interior / National Park Service, www.havrehillpreservation.org/havre%20mpd%20revised%20CZ%20and%20KH%20march-1.pdf. Accessed 11 Mar. 2026.

Helena Independent Record. “Christmas in the Cooler: The Prohibition Raids of 1925 Made Holiday Less Cheery.” Helena Independent Record, 24 Dec. 2024, helenair.com/news/state-regional/christmas-in-the-cooler-the-prohibition-raids-of-1925-made-holiday-less-cheery/article_fe14f663-af8a-53e4-a081-0884994d62e6.html. Accessed 11 Mar. 2026.

Montana Right Now. “Hometown Proud: Havre’s Hidden Underground Treasure.” Montana Right Now, www.montanarightnow.com/news/hometown-proud-havres-hidden-underground-treasure/article_e2e6fed1-9f51-5faa-8010-1b7be2952e97.html. Accessed 11 Mar. 2026.

Outside Bozeman. “Book: Honky-Tonk Town.” Outside Bozeman, outsidebozeman.com/culture/culture-more/books/book-honky-tonk-town. Accessed 11 Mar. 2026.

Roadside America. “Havre Beneath the Streets, Havre, Montana.” Roadside America, www.roadsideamerica.com/story/14587. Accessed 11 Mar. 2026.

Walsh, Ben. “Folklore and Mystery: Underneath Montana’s Streets.” Distinctly Montana, www.distinctlymontana.com/folklore-and-mystery-underneath-montanas-streets. Accessed 11 Mar. 2026.

Whistling Andy. “Running of Moonshine from Canada to Montana During Prohibition: The Bootlegger Trail.” Whistling Andy, 1 Aug. 2023, whistlingandy.com/blogs/the-blog/running-of-moonshine-from-canada-to-montana-during-prohibition-the-bootlegger-trail. Accessed 11 Mar. 2026.

Wilson, Gary A. Honky-Tonk Town: Havre, Montana’s Lawless Era. Globe Pequot Press, 2006. Excerpt republished in Distinctly Montana, www.distinctlymontana.com/honky-tonk-town-havre. Accessed 11 Mar. 2026.​​​​​​​​​​​​​​​​