Alyssa Osborn was driving south on Interstate 65 near Seymour early Sunday when a Jeep traveling the wrong way slammed into her Ford Escape. The crash killed the 31-year-old Scottsburg mother at the scene. Her 1-year-old son, Waylon Osborn, was badly hurt and later died at a Louisville children’s hospital.
The crash happened shortly after 2:30 a.m. on Aug. 23 in Jackson County, about one mile south of Seymour. A caller reported a head-on crash in the southbound lanes near the 48-mile marker. Indiana State Police sent troopers and its Crash Reconstruction Team to the scene.
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Investigators said 51-year-old Theosco Middlebrooks of Louisville was driving a 2005 Jeep Liberty north in the southbound lanes. Police have not said why he was traveling against traffic. His Jeep hit Osborn’s 2023 Ford Escape head-on as she was traveling south in the proper lanes.
The impact was fatal for both drivers. Osborn and Middlebrooks suffered deadly injuries and were pronounced dead at the scene by the Jackson County Coroner’s Office. For Osborn’s family, the crash quickly became even more painful because her young son was also inside the vehicle.
Waylon was properly restrained in the rear passenger seat of the Ford Escape when the collision happened. He survived the initial impact but suffered critical injuries. Emergency crews took him to Norton Children’s Hospital in Louisville, where he later died from injuries caused by the crash.
Investigators believe alcohol consumption by Middlebrooks likely played a role in the collision. That finding has not yet been made final. Toxicology results were still pending, and the investigation into what led Middlebrooks to enter the southbound lanes remained underway.
The crash shut down all southbound lanes of I-65 near Seymour for about four hours while investigators examined the wreck and crews cleared the roadway. Several agencies assisted, including the Indiana State Police Crash Reconstruction Team, Seymour police, the Jackson County Sheriff’s Department, emergency medical crews, local fire departments and the Jackson County Coroner’s Office.
The deaths of Alyssa and Waylon turned a late-night highway crash into the loss of a mother and her young child from Scottsburg. Authorities have not released any further details about the family beyond the information connected to the crash. The investigation remains open as police await toxicology results and work to establish the full circumstances.
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