Theosco Middlebrooks, 51, was driving the wrong way on Interstate 65 near Seymour early Sunday when his Jeep crashed head-on into a Ford Escape. The crash killed Middlebrooks and the woman behind the wheel of the SUV, 31-year-old Alyssa Osborn of Scottsburg. Osborn’s 1-year-old son, Waylon, also died after being critically injured.
The collision happened shortly after 2:30 a.m. Sunday, Aug. 23, on southbound I-65 in Jackson County. The crash site was about one mile south of Seymour, near the 48-mile marker. Indiana State Police said a caller alerted authorities to a head-on crash in the southbound lanes.
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Police said Middlebrooks, who was from Louisville, Kentucky, was driving a 2005 Jeep Liberty northbound in lanes meant for southbound traffic. Investigators have not said why he ended up traveling against traffic.
The Jeep struck Osborn’s 2023 Ford Escape head-on. Osborn was driving southbound when the two vehicles met on the interstate. The crash was so severe that both drivers suffered fatal injuries and were pronounced dead at the scene by the Jackson County Coroner’s Office.
Osborn’s son was also inside the Ford Escape. Police said the 1-year-old was properly restrained in a rear passenger seat. He suffered critical injuries and was taken to Norton Children’s Hospital in Louisville for treatment.
The boy later died from those injuries. His death meant three people were lost in a single crash that began with a vehicle traveling in the wrong direction on a busy interstate.
Investigators believe Middlebrooks had consumed alcohol and that it likely played a role in the collision. Police have not presented that as a final determination. Toxicology results are pending, and the investigation into what caused the crash is still underway.
Southbound I-65 near Seymour remained closed for roughly four hours as investigators worked the scene and crews removed the damaged vehicles and debris. The Indiana State Police Crash Reconstruction Team is investigating the collision.
The case now centers on a simple but unanswered question: why was Middlebrooks driving north in the southbound lanes? Investigators are still piecing that together. What is already clear is that the wrong-way crash ended three lives, including those of a mother and her 1-year-old son.
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