Wrong Way Crash on I-65 Near Seymour Claims Three Lives

Crash remains under investigation

Early Saturday morning a two-vehicle crash involving a wrong way driver claimed three lives on I-65 near Seymour, in Jackson County, Indiana. 

Shortly after 2:30 am, a caller reported a head on crash on I-65 Southbound just south of the 48-mile marker in Jackson County.  The crash occurred approximately one mile south of Seymour.  Responding officers quickly determined the crash involved fatalities and requested the Indiana State Police Crash Reconstruction Team to conduct the investigation.

The initial investigation determined that, for an unknown reason, a 2005 Jeep Liberty being driven by Theosco Middlebrooks, age 51, Louisville, Kentucky was traveling northbound on I-65 in the southbound lanes, just south of the 48-mile-marker.  Middlebrooks’ vehicle collided head on with a 2023 Ford Escape being driven by Alyssa Osborn, age 31, Scottsburg, Indiana, that was traveling southbound in the southbound lanes. 

Tragically, both Middlebrooks and Osborn sustained fatal injuries.  They were both pronounced deceased on the scene by the Jackson County Coroner’s Office.  The one-year-old infant son of Osborn, Waylon Osborn, who was properly restrained in the rear passenger seat of the Ford Escape, sustained critical injuries in the collision.  He was transported to Norton Children’s Hospital in Louisville, Kentucky where he was later pronounced deceased due to injuries sustained in the crash.

The investigation is ongoing.  Investigators believe that alcohol consumption by Middlebrooks likely played a role in the crash.  Toxicology results are pending.        

All southbound lanes of I-65 just south of Seymour were closed for approximately four hours for crash investigation and cleanup.

Both families have been notified.

The Indiana State Police Crash Reconstruction Team was assisted by Troopers with the Indiana State Police-Versailles Post, Seymour Police Department, Jackson County Sheriff’s Department, Jackson County EMS, Seymour Fire Department, Redding Fire Department, Vernon Township Fire Department, and Jackson County Coroner’s Office.