Theosco Middlebrooks was driving north on Interstate 65 early Sunday, but he was in the southbound lanes near Seymour. Minutes later, his Jeep collided head-on with a Ford Escape carrying 31-year-old Alyssa Osborn and her 1-year-old son, Waylon. All three people died from injuries suffered in the crash.
Indiana State Police said the collision was reported shortly after 2:30 a.m. Aug. 23 in Jackson County. The crash happened just south of the 48-mile marker, about one mile south of Seymour. A caller alerted authorities to the head-on collision in the southbound lanes.
Middlebrooks, 51, was from Louisville, Kentucky. He was driving a 2005 Jeep Liberty northbound in lanes meant for southbound traffic. Investigators said they did not yet know why the Jeep was traveling the wrong way when it struck Osborn’s vehicle.
Osborn, who lived in Scottsburg, was driving a 2023 Ford Escape southbound in the correct lanes. The Jeep and Ford collided head-on, leaving both drivers with fatal injuries. The Jackson County Coroner’s Office pronounced Middlebrooks and Osborn dead at the scene.
Osborn’s 1-year-old son, Waylon, was also inside the Ford Escape. Police said the child was properly restrained in the rear passenger seat. He suffered critical injuries and was taken to Norton Children’s Hospital in Louisville for treatment.
Waylon later died at the hospital from injuries suffered in the crash. His death brought the total number of people killed in the collision to three. What began as a wrong-way crash on a southern Indiana interstate ended with the deaths of two adults and a child.
Police believe alcohol consumption by Middlebrooks likely contributed to the crash. Toxicology testing was still pending, so investigators had not reached a final conclusion about the role alcohol played. The Indiana State Police Crash Reconstruction Team continued working to determine exactly how the Jeep entered the southbound lanes.
The southbound side of I-65 remained closed for about four hours while police investigated the scene and crews cleaned up the wreck. Seymour police, the Jackson County Sheriff’s Department, emergency medical personnel, Seymour Fire Department, Redding Fire Department, Vernon Township Fire Department and the Jackson County Coroner’s Office also assisted.
The investigation remains ongoing. At this stage, authorities have confirmed the direction of travel, the vehicles involved, the deaths of all three people and the pending toxicology results. The crash happened on Interstate 65 about one mile south of Seymour in Jackson County, Indiana.
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