Alyssa Osborn, 31, was driving south on Interstate 65 near Seymour early Sunday when a Jeep came toward her in the wrong direction. The head-on crash killed Osborn at the scene and later claimed the life of her 1-year-old son, Waylon. The driver of the Jeep, 51-year-old Theosco Middlebrooks of Louisville, Kentucky, also died.
The crash happened shortly after 2:30 a.m. Sunday, Aug. 23, on southbound I-65 in Jackson County, about a mile south of Seymour. Indiana State Police said a caller reported a head-on collision near the 48-mile marker. Troopers and emergency crews arrived and quickly found that the crash had left people with fatal injuries.
Investigators said Middlebrooks was driving a 2005 Jeep Liberty northbound in the southbound lanes. For reasons that remain unclear, he was going the wrong way on the interstate when the Jeep slammed head-on into Osborn’s 2023 Ford Escape.
Osborn and Middlebrooks both suffered fatal injuries and were pronounced dead at the scene by the Jackson County Coroner’s Office. There was little anyone could do after the collision. The force of the crash left both drivers dead before they could be taken to a hospital.
Osborn’s young son, Waylon, was in the Ford Escape with her. Police said the boy had been properly secured in a rear passenger seat. He survived the initial crash but suffered critical injuries and was taken to Norton Children’s Hospital in Louisville.
Waylon later died at the hospital from his injuries. His death turned an already deadly highway crash into a tragedy involving a mother and her young child, along with the driver whose vehicle had crossed into the wrong lanes.
Investigators believe alcohol consumption by Middlebrooks likely played a role in the crash. That remains a preliminary finding, however. Toxicology results are still pending, and state police have not yet said exactly why Middlebrooks entered the southbound lanes.
The crash shut down all southbound lanes of I-65 near Seymour for about four hours while investigators examined the wreckage and crews cleared the roadway. The Indiana State Police Crash Reconstruction Team is handling the investigation, which remains ongoing.
For now, the known facts are stark. A driver was traveling the wrong way on a major interstate before dawn. His Jeep struck an SUV carrying a mother and her 1-year-old son. Three people died, and investigators are still working to determine exactly what led to the fatal turn onto the wrong side of the highway.
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