The year 1926 was shaping up to be a promising one in this bustling city of 23,000, with the oil business waning and a robust and vibrant steel and manufacturing presence waxing. The city’s fortunes were on the rise and John Collins “Jack” Dempsey, now in his eleventh year as police chief, was determined to show he would squash the rising tide of crime and anti-prohibition activity—activity that had prompted public outrage and uproar due to the gory violence reported daily in the press. The demeaning headline “Little Chicago” appeared frequently in the morning and evening papers, comparing the growing gangland activity around Olean to that of the gangster-ruled city of Chicago. Even the extremely popular Dempsey felt the pressure to respond in a dramatic way. 

Thus, the news of Capone’s possible stopover in town came at an auspicious time.

At the end of the previous century, waves of immigrant workers from Ireland, Italy, Poland and the Ukraine began to add to the population of the city, moving into the North Olean industrial section of town. Drawn by the opportunities and freedoms of America, including the vibrant social life of the neighborhood, they wanted their liquor. Meanwhile, the moneyed class living in the stately mansions clustered in the center of the city atop Oak Hill looked with disdain on the growing abuses against the 18th Amendment and the 1920 Volstead Act, which they had worked so hard to achieve. 

The police were not the only ones to whom establishments made “donations.” Bootleggers not only received payment for their product, but a premium was included for “protection” from ruffians who might try to convince the owner to buy from them instead. Such expenses were high, but the profits derived from the sale of beer and alcohol were lucrative enough to ensure success. Many corner grocery stores operated their own version of a speakeasy by selling the illegal beverages from behind a counter. It was an accepted practice in cities and small communities all over the United States.

Police Chief Dempsey had kept the illegal activity out of the public eye by maintaining a semblance of law and order. His rule was simple: no violence or disorderly conduct and the police will not shut you down. This seemed to satisfy the Prohibition factions while placating the businessmen who profited mightily from the illegal sale and distribution of beer and whiskey to a thirsty working-class population. The system had worked well, but the lure of easy money had increased the number of competing “outfits.” By 1926, the fragile peace was beginning to unravel as each group vied for supremacy, sometimes violently.

The voices of temperance in the Olean area—and there were many of them—were vocal, influential and well-financed. And they were not happy at all with the nefarious elements working the area’s illegal alcohol trade. The fight to ban the sale and distribution of alcohol had been a long and laborious one, and they were not about to stand by while the laws they had worked so hard to enact were ignored. 

The Women’s Christian Temperance Union was formed with the backing of women’s suffrage proponents such as Elizabeth Caty Stanton and other temperance supporters, who pressed the organization to push for universal suffrage. The suffragettes believed political power would provide the means to implement prohibition. Both goals were achieved with the ratification of the 18th and 19th amendments in 1919 and 1920. Little did they realize that temperance would spur the rise of bootlegging and organized crime. 

Olean’s wild-west, boom-town mentality of the late 1800s attracted the attention of prohibitionists and suffragettes like Fanny Bartlett, wife of influential Olean banker Frank Bartlett, who helped establish the Olean chapter of the W.C.T.U. Likewise, an influential W.C.T.U. chapter sprung up in Cuba, 15 miles north and east of Olean, while a W.C.T.U. fountain was dedicated in the Village of Allegany in 1910 as another sign of the organization’s powerful presence in the area.

Colorful behavior was typical for this well-respected and feared lawman. While he loved boxing and baseball, he was also known to enjoy less legitimate pastimes such as shooting craps and attending cock fights in one of the many clubs, taverns or dancehalls where illegal liquor flowed freely. One of these was his friend Joe Lippert’s place, a roadhouse on Rock City Hill Road, south of the city. Of course, such behavior raised many an eyebrow among the well-heeled upper crust, but his popularity with the common people, plus the fact that he did maintain “law and order” in this otherwise raucous environment, kept him above inquiry or reprimand. 

Stories circulated about his frequent use of a thick wad of hundred-dollar bills to take advantage of good bets that came his way while he participated in the games of chance. Many wondered how a policeman could have such a stash of cash. But not even the mayor was allowed to enter Dempsey’s office in the police headquarters on Whitney Avenue, along the tracks near the intersection of North Union and Sullivan Street, where train station was located. 

Over the years, the Olean Police Department adopted his colorful personality. While he never carried a gun himself, he insisted that his officers were always “ready for action” and in full dress uniform, even when walking the beat. Each was armed with just a “Billy club” or blackjack, a seven- or eight-inch iron shaft covered with hardened leather, to enforce the law. In one of the many stories defining this tough image, a young officer walking the beat in the North Olean section of the city encountered four rowdy characters who determined that they should test this reputation. The officer, realizing that he “might work up a sweat in the ensuing encounter, took off his jacket and laid it carefully aside so as not to soil it.” The four assailants were overwhelmed by the young officer and his leather-wrapped iron club. Later, amid cries of police brutality, Dempsey reprimanded his officer for “acting out of uniform.”

Dempsey’s own ability to handle himself in a fight further enhanced this reputation of toughness for his officers. On more than one occasion, he rendered groups of noisy or annoying restaurant patrons or law-breaking street urchins’ unconscious using only his fists.  But while “keeping the peace” was paramount, curbing the illegal sale of liquor and beer seemed to exist under a different set of standards during the first seven years of Prohibition. Only when one of the most notorious local bootleggers began a reign of terror and violence did Dempsey lay down his heavy-handed brand of peacekeeping. 

Alberto Verrusio Ricci, better known as “Buffalo Al Ritchie,” was an Olean-Salamanca-Bradford rum runner and supplier who moved to Olean from Buffalo and soon opened an establishment two miles north of the city on the Buffalo Highway (Route 16) called the Sunset Inn. Ritchie’s very successful liquor and beer distribution business grew, while the rather obvious sale of illegal alcohol in his own very popular establishment began to siphon off customers and profits from his own bootlegging customers. In response, his rivals retaliated with a series of violent attacks on Ritchie’s well-established supply network out of Buffalo. A brutal series of shootings and killings, like those in Chicago, soon erupted in the tri-city area as Ritchie killed and intimidated those who crossed him. This gangland activity earned the “Little Chicago” moniker for the city of Olean. 

By the late summer of 1926, Chief Dempsey realized that Capone’s arrival could only serve to further escalate the violence and mayhem. 

Nearly a century has passed since the reported “sightings” of Al Capone and his confrontation with the equally legendary chief of police, Jack Dempsey. Over the years, the meeting has grown to mythological proportions. While some versions of the events of that September are highly unlikely, one is certainly very plausible. 

One thing is certain. As Capone himself said at his arrest in Philadelphia in May 1929, “I was arrested for disorderly conduct in a little place called Olean, N.Y.” What has remained the fodder for myth building is the time, place and circumstances of this arrest. The reason is simple—neither Capone, nor Dempsey, ever revealed an exact date for Capone’s “arrest,” and police records of any such event are nonexistent.  Various versions of the legend say Capone had settled in for the night at the Central Hotel when Dempsey “knocked at his door,” demanding that he “leave the next morning or be dragged up and down Union Street and arrested for vagrancy.” Another version suggests that Capone was confronted by Dempsey outside the Olean House, where the policeman told him to “get out of town.” Capone, it is said, “spit on the ground” and was arrested on the spot for disorderly conduct. Still another claims that Capone “begged” to be arrested to protect himself from being killed by assassins who were looking for him. 

Here, then, is an analysis of the most popular “sightings.” 

The first was uncovered by the late Dr. James Martine of St. Bonaventure University. While researching material for a book, he came across a New York Times article from May 18, 1929, concerning Capone’s arrest in Philadelphia. In the article, Capone admits that he was arrested in Olean. Martine places Capone in Olean in 1919, around the time that Capone’s mentor, Johnny Torrio “transferred” Capone from New York City to Chicago so he could “lie low” after being involved with the fatal beating of a gang member in a saloon brawl. He cites John Kobler’s classic 1971 biography, The Life and World of Al Capone, which mentions the same quote, as well as another book, Bloodletters and Badmen: An Encyclopedia of American Criminals, written by Jay Nash in 1987, in which the 1919 date is given for the arrest in Olean. 

It certainly would have been possible for Capone to take the train from New York to Chicago through Olean, make the “half-way” stop, and then be confronted by Dempsey. But Dempsey never confirmed the 1919 date. In fact, he never identified Capone at all. Instead, he simply said that he had “arrested many ‘hoodlums’ in those early years of prohibition, but,” he added, “not Capone.”  

The year 1926 also fits perfectly with events developing outside Western New York. In his 1993 book, Mr. Capone: The Real—and complete—Story of Al Capone, author Robert Schoenberg details the escalating war between Capone’s South Side operation and that led at the time by Earl J. “Hymie” Weiss on Chicago’s north side, which resulted in an attempt on Weiss’ life on September 20. Schoenberg observes that, “Many times Capone had been east during the first three weeks of September 1926, to arrange for supplies of smuggled booze” to compete with Weiss’ north siders.

So, it is highly probable that Alfonse Capone did make a stop in Olean in 1926 to arrange for a reliable supply of coveted Canadian whiskey. He may even have stayed overnight, or simply dined at the Olean House with potential suppliers. However, right up until his death in 1964, Jack Dempsey, the long-serving police chief who arrested the notorious bootlegger, never spoke about the incident in public.

But just 35 miles south and east of Olean, in Coudersport, PA, another Capone adversary did gain notoriety for his confrontation with the gangster. Eliot Ness, who led an elite unit of federal agents in raiding and destroying Capone’s alcohol-making infrastructure in 1931, moved to the Pennsylvania village in late 1956, but died there just eight months later, on May 16, 1957. Just before his death, Ness collaborated with writer Oscar Fraley on a book titled, The Untouchables. His memoirs became the basis for a 1958 television series of the same name and a later motion picture starring Kevin Costner. An Eliot Ness Museum, located on Main Street in the village, opened to the public in 2019. An Eliot Ness festival followed the opening of the museum that summer, but COVID-19 restrictions cancelled the event in 2020 and 2021. Organizers are hoping for a return of the festival in 2022.

Stephen Cocca, a retired middle school social studies teacher, lives in Olean with his wife Vicki. One of his favorite shows growing up was “The Untouchables.”