‘Woebegone little character’ John O’Leary opened fire in Butte federal court 100 years ago (2024)

COLIN HANSONfor The Montana Standard

“He was the most nondescript little fellow, kind of a woebegone little character. He just didn’t look like the kind of guy who’d cause any problems.”

Butte resident Kathy Maloney, interviewed by The Montana Standard in March 2002, was describing a regular customer in the 1960s at her parents’ bar, The Cheery Lounge at 73 W. Park St. She described a tragicomic figure — a man in his 80s with long white hair, sporting a Panama hat and red pants tucked into Wellington boots; she recalled how he had appeared one day with his arm in a sling after falling off a table while dancing a polka at the M&M.

And she remembered how her father had explained to her that this “funny little guy” was in fact John O’Leary, the convicted bootlegger who, 100 years ago this month, shot up the federal courthouse on Main Street.

O’Leary, known to his family and friends as Jack, was born in Iowa in 1880, the third of seven children of William and Katherine O’Leary. William was a railroad man whose work led him across the West, before he settled with his growing family in Butte in 1891. Their eldest son James was one of the youngest victims of the Kenyon-Connell Warehouse explosion of 1895.

After leaving school O’Leary worked as a smelterman until his father’s connections led to a position with the Northern Pacific Railway in 1902, and for the next two decades he followed in his father’s footsteps. By 1905 he was a switchman for the Great Northern, by 1918 a foreman, and a notice in The Butte Miner in 1921 referred to him as “grievance man for the GN.”

O’Leary was also a prominent member of the city’s Democratic Party. In March 1912, he ran as a candidate for alderman for Butte’s seventh ward, losing to the socialist Edmund Ladendorff. In April that year he was hailed as a hero after risking his life to help evacuate the Olson Block on South Wyoming Street during a ferocious blaze that caused $350,000 in damage.

Throughout this period, O’Leary lived next door to his parents at 814 George St. Contemporary news reports and society notices describe a highly respected and close-knit family. In 1922 his parents left Butte for Los Angeles. Whether O’Leary’s subsequent misfortunes can be linked directly to their absence is debatable, but it is a matter of record that in the months immediately following their departure his life took a precipitous downturn.

The 1923 city directory records an abrupt career change, listing O’Leary as manager of the Montana Cigar Store at 25 S. Main St. According to federal dry agents the business was a front for a liquor store and gambling house, and it was here on Jan. 11, 1924, that O’Leary was arrested for violation of prohibition laws. On May 20, 1924, he was found guilty at the federal court of possessing and selling intoxicating liquors, and his sentencing was scheduled for the following, fateful day.

During his subsequent trials, friends and family members detailed O’Leary’s decline. It was a story of mounting gambling debts and increasingly erratic and paranoid behavior. All agreed that his long-term fiancée’s marriage to another man pushed him over the edge, leading to frequent talk of suicide. His younger sister Josephine tearfully described how he had appeared at her home the night before his sentencing “in a state of wild excitement” asking her if she owned a gun and threatening to “end everything”.

On the morning of May 21, 1924, O’Leary appeared at the federal court to receive his sentence from Judge Charles N. Pray. As his case was called by the Deputy Clerk he rose from his seat, pulled two .32 caliber revolvers from his pockets, and took aim at the four federal agents he believed had wronged him. It is fair to surmise that O’Leary was not an experienced marksman. Not one bullet hit its target. Instead, they ricocheted around the ornate courtroom, spraying the walls, ceiling, doorframes and, most notably, the judge’s bench, missing Judge Pray by a matter of inches. The bullet hole is still visible today.

The only person injured in the shooting was O’Leary himself. It remains disputed whether that shot was self-inflicted or fired by a federal agent. However, a letter written by O’Leary and addressed to his mother, found in his room in the Goldberg Block at Park and Dakota after the shooting, supports the notion of attempted suicide. In doing so it also provides a disturbing indication of his state of mind at the time:

“My Dear Mother: I am about to do something. I know it will make you feel badly, but I can’t help it — something keeps telling me to do it. You know I never did anyone harm in this world but myself, and when a lot of rats, better known as friends, send one to jail for nothing it’s about time to leave, and I will take as many rats with me when I go. It’s high time for one to take the law in his own hands when they can send a man to jail for nothing. So good-bye, mother. I will meet you in heaven. So cheer up. I am doing only a humanitarian act. Kiss little Ralph for me — and say good-bye to father and Will. JACK.”

O’Leary was given last rites at the courthouse, but after being admitted to hospital he staged an unexpected recovery. By June 6, he was well enough to be charged with the attempted murder of the four federal agents, and upon his discharge from hospital he was indicted by a Helena grand jury.

On Oct. 17, O’Leary was sentenced to 90 days in jail and fined $100 for the original bootlegging conviction, and upon his release in December he was transported to the Butte courthouse to appear before Judge George M. Bourquin and face the attempted murder charges. In an unusual defense for the time, attorney George D. Toole hired R.B. Tracey, a neurologist from Warm Springs Hospital, who testified that O’Leary’s actions were “due to emotional insanity … a complete disassociation of personality”.

On Christmas Day, after 22 hours of deliberation, an angry Judge Bourquin dismissed the deadlocked jury and reset the hearing for the following month in Helena, only to have his fury further stoked when, on Jan. 19, 1925, the Helena jury unanimously found O’Leary not guilty due to insanity.

After his acquittal, O’Leary was able to rebuild his life, returning to the Great Northern as a switchman, before joining his mother in Los Angeles after his father’s death in 1930. For the next 20 years, he worked as a conductor for the Santa Fe and California Southern railroads, eventually returning to his large extended family in Butte after his mother’s death in 1955. He would remain in the city for the rest of his life.

O’Leary died on Feb. 9, 1969, from injuries sustained after a fall at the boarding house at 53 W. Park St. (now the Miner’s Hotel) just yards from his favorite haunt, The Cheery Lounge. His body was interred in the paupers’ field at Holy Cross Cemetery on Feb. 16, 1969.