Biographical Information: Orlando Lester

A long-time servant to the Whit Owens family, Orlando Lester, was a tenant of Will Mathis in November 1901. Lester's history with the Owens clan included helping to defend the family during a raid by revenuer officers.When Lester found himself in trouble with the law (once for being caught with a white girl and for distilling), he always relied on Whit Owens to get him out of it. That assistance guaranteed Lester's true loyalty to Owens. In an effort to get rid of witnesses against himself and reportedly following a plan Owens developed, Lester attempted to murder Walter Jones, missed and killed Hamp Williams. Though witnesses identified Lester as the probable shooter, he was not arrested and did not serve time for that crime.

One of four men accused in the murders of the U.S. Marshals, Orlando Lester gave several contradicting stories about the events of that night. He, along with Will Mathis, was found guilty and sentenced to death by hanging. During the ride to the gallows, Lester is said to have admitted firing the fatal shots, though claimed he was forced into it by Mathis and Owens. He was executed on November 26,1902 at 12:50 pm before a crowd of 7,000.