On November 6, 1889, a schoolgirl named May Leith, whose age was reported variously as 14, 15, or 17 in different contemporary accounts, was reportedly chased and assaulted near Leesburg, Virginia, by an assailant whose head was covered with a "guano sack" (a cloth fertilizer bag). She was unable to positively identify her attacker but named, or was reported to have named, Orion Anderson, a 14-year-old African American boy, sometimes referred to in newspapers as "Owen" Anderson. Newspaper accounts differ on the sequence of events: the Richmond Daily Times reported Anderson was released after an initial accusation and then rearrested based on circumstantial evidence, after which he apparently confessed. The Richmond Dispatch reported that a "guano sack" believed to have been used in the assault was found, and that Anderson was said to have confessed and was placed in the Leesburg jail.
Two days after the alleged assault, at approximately one in the morning on November 8, 1889, a mob took Anderson from his jail cell. Accounts of the mob's size differ: the Daily Times reported around a hundred armed men who seized jail keys from Officer Charles F. Laycock, while the Richmond Dispatch described a smaller group of up to thirty disguised men who tricked the jailer by having two undisguised men lead a third man dressed as a prisoner into the jail. Deputy Sheriff Laycock stated he could not identify the undisguised men because they were strangers not local to the county. Anderson was hanged at the freight depot and also shot — in the head, body, and leg, according to the Richmond Dispatch account. The Washington Post, in a report published November 9, 1889, stated "The work was done quietly but effectually." No one was ever convicted in connection with Anderson's killing. Virginia did not enact an anti-lynching law until 1928, and lynching was not recognized as a federal offense in the United States until 2022.
Anderson's case was the second of three recorded lynchings in Loudoun County, Virginia, between 1880 and 1902. Recent research by the Loudoun County Freedom Center, using census records, identified Anderson's actual birth year and highlighted inaccuracies in contemporary press coverage; Michelle Thomas of the Loudoun County NAACP has said Anderson's age was exaggerated in some reports, which described him as 19 or 20 years old. A 2019 interpretive marker, developed by the Northern Virginia Regional Park Authority (NOVA Parks) and the Loudoun County Chapter of the NAACP, was placed at the site of the old rail station where he was killed. It notes Anderson was the son of Thomas and Charlotte Anderson, had nine siblings, and was buried at Potter's Field, a burial ground for the poor and unknown. On Juneteenth (June 19) 2019, about 200 people gathered to march from the old jail to the lynching site as part of the Loudoun County Remembrance and Reconciliation Initiative; soil from the site was later sent to the National Memorial for Peace and Justice in Montgomery, Alabama.