On a chilly Saturday afternoon in November 1901, Hugh Montgomery, a 25-year-old White male serving as a field deputy for the United States courts, embarked on a mission that would end in tragedy near the small village of Delay in Lafayette County, Mississippi. Accompanied by his brother, Special Deputy John A. Montgomery, he traveled from Oxford to the home of Will Mathis to serve a warrant for illicit distilling.
Upon their arrival, Mathis offered no resistance and, feigning hospitality, invited the lawmen to spend the night in his home rather than return to town in the dark. Trusting the suspect after ensuring no weapons were visible, the brothers accepted the offer and retired for the evening, unaware of the conspiracy forming against them.
Under the cover of darkness, Mathis left the premises and secured a firearm from a neighbor, aided by an accomplice named Orlando Lester. Returning to the house in the early morning hours of November 17, the perpetrators ambushed the sleeping officers, shooting them dead before setting the structure ablaze in an attempt to destroy the evidence. The smoldering ruins were discovered later that morning by neighbors, and amidst the ashes, the charred remains of the two deputies were found. Hugh Montgomery's body was identified by his brother Dave, who recognized a distinctive gold tooth among the remains.
The brutal nature of the crime ignited an immediate and intense investigation by local authorities and the community. Suspicions quickly fell on Will Mathis, who was apprehended shortly after the incident. Further inquiry led to the arrest of Orlando Lester, a laborer associated with Mathis, as well as other alleged accomplices including Bill Jackson and Mathis's father-in-law, Whit Owens. Testimony revealed that the officers had been killed while defenseless, and the subsequent cover-up involving the arson only fueled the public's demand for justice.
Legal proceedings moved swiftly against the primary suspects. Will Mathis and Orlando Lester were tried and convicted for the murders of the Montgomery brothers. Despite appeals and temporary stays of execution granted by the governor, the convictions were upheld. On September 24, 1902, both Mathis and Lester were executed by hanging for their roles in the double homicide. The trials of the other alleged conspirators resulted in varying sentences, with Bill Jackson receiving prison time, bringing a grim conclusion to one of the most notorious crimes in the region's history.
