In the autumn of 1907, the life of Sheriff Charles Henry Oglesby, a 41-year-old White male, was cut tragically short in Winamac, Indiana. On October 5th, what began as a seemingly routine request to remove three men from a Pennsylvania Railroad freight train escalated into a fatal confrontation. The train's engineer had encountered the individuals stealing a ride at a stop in Star City and sought the sheriff's assistance when they refused to leave.
Unbeknownst to Sheriff Oglesby, these were not ordinary vagrants but a gang of safe-crackers fresh from a burglary in nearby Burnettsville. As he approached, the situation quickly unraveled. One of the suspects fled, while the other two opened fire on the sheriff. Despite being gravely wounded with a shot to the chest, Sheriff Oglesby managed to return fire, striking one of his assailants in the abdomen. He succumbed to his injuries several hours later at his home, surrounded by his family. At the time of his death, he had served with the Pulaski County Sheriff's Department for a mere ten months and was survived by his wife and three children.
In the aftermath of the shooting, a posse was quickly formed to track down the responsible parties. Their efforts led them to a cornfield north of Winamac, where two of the wounded suspects were discovered and surrendered without a fight. The third man was apprehended along the railroad tracks. The suspect that Sheriff Oglesby had shot ultimately died from his injuries. The remaining two men were tried for their crimes and sentenced to prison.
