Two adults and a 1-year-old boy died early Sunday after Theosco Middlebrooks drove the wrong way on Interstate 65 and crashed head-on into another vehicle near Seymour, Indiana State Police said. The crash closed southbound Interstate 65 for about four hours while investigators worked the scene.
Jackson County crash
A caller reported the head-on collision just after 2:30 a.m. in the southbound lanes of Interstate 65 in Jackson County, about one mile south of Seymour. Investigators determined that Middlebrooks, a 51-year-old from Louisville, was traveling northbound in the southbound lanes in a 2005 Jeep Liberty when he hit a 2023 Ford Escape driven by 31-year-old Alyssa Osborn of Scottsburg.
Middlebrooks and Osborn died at the scene. Osborn's 1-year-old son, Waylon, was critically injured and later died at a hospital.
Waylon and Osborn
Police said Waylon was properly restrained in a car seat in the rear passenger side of the vehicle. That detail is the clearest account yet of where the child was seated during the crash, and it places the focus on the force of the impact rather than on any restraint failure.
Indiana State Police said investigators believe alcohol consumed by Middlebrooks likely played a role in the crash. As of Sunday evening, toxicology results were pending, leaving the criminal and medical findings on separate tracks for now.
Interstate 65 cleanup
For drivers on that stretch of Interstate 65, the immediate disruption was the four-hour closure of all southbound lanes just south of Seymour. Investigators and cleanup crews remained on scene through the morning, and the next step in the case rests on the pending toxicology results and the cause of the wrong-way travel.
What caused Middlebrooks to drive northbound in the southbound lanes remains the central unanswered question.







