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On Sunday, the NYPD’s 19th Precinct acknowledged the 139th anniversary of the line-of-duty death of Roundsman (Sergeant) Robert Montgomery — a tragic and little-known chapter of Upper East Side history.
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“Today marks the 139th anniversary of the line-of-duty death of 19th Precinct Roundsman (Sergeant) Robert Montgomery,” the precinct wrote in a post on X. “On January 11, 1887, he succumbed to gunshot wounds sustained three days earlier. On this day, and always, his sacrifice will never be forgotten.”Montgomery’s death occurred under extraordinary circumstances. According to historical accounts, he was shot by an officer he had been assigned to supervise while conducting routine post inspections.
During his rounds, Montgomery discovered that one officer was absent from his post. He eventually located the officer inside a bar, seated near a fire with his hat off and jacket open. The officer’s belt and club were resting at his side — a clear violation of duty at the time.
“While making his rounds Montgomery found that [Police Officer William] O’Rourke was off his beat, and instituted a search to find him,” reads a New York Times report published after the incident. “Finally he discovered him in a shanty at the corner of Madison-avenue and Seventy-third street, where the police officer had gone to escape the severity of the cold.”
When Montgomery confronted him and said he intended to file a complaint, he ordered the officer back to his post. As the two walked together to the area of 73rd Street and Madison Avenue, the officer suddenly drew his revolver and fired at Montgomery. After the first shot struck him, Montgomery turned away — at which point the officer reportedly said, “I’ll fix you,” and fired again.
Despite his injuries, Montgomery managed to wrestle the revolver away before collapsing. He was taken to the hospital, where he died from his wounds three days later, on January 11, 1887.
The officer was arrested, charged with murder, convicted after a jury trial, and sentenced to life in prison.
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Montgomery had served with the department for a decade and was the first officer from the 19th Precinct to be killed in the line of duty. He was survived by his wife and young son. According to historical records, his son never had children and died a widower in 1966, having lived later in life in Stanhope, New Jersey.Today, Roundsman Montgomery’s photograph hangs inside the current 19th Precinct station house on East 67th Street — a quiet but enduring reminder of a sacrifice made more than a century ago, and of a moment in Upper East Side history that continues to resonate.
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