Alyssa Osborn and Son Waylon Accident: Mother and 1-Year-Old Son Killed in Wrong-Way I-65 Crash Near Seymour, Indiana
A heartbreaking tragedy on Interstate 65 near Seymour, Indiana, has claimed the lives of a young mother and her 1-year-old son following a devastating wrong-way collision early Sunday morning.
The victims have been identified as 31-year-old Alyssa Osborn of Scottsburg and her 1-year-old son, Waylon Osborn. The two were traveling southbound on I-65 in Jackson County when their vehicle was struck head-on by a Jeep traveling in the wrong direction.
According to Indiana State Police, the crash occurred shortly after 2:30 a.m. on August 23, 2026, approximately one mile south of Seymour near the 48-mile marker. Investigators determined that a 2005 Jeep Liberty driven by 51-year-old Theosco Middlebrooks of Louisville was traveling north in the southbound lanes of the interstate.
Middlebrooks’ Jeep collided head-on with a 2023 Ford Escape driven by Osborn. The impact proved fatal for both adults. Osborn and Middlebrooks were pronounced dead at the scene by the Jackson County Coroner’s Office.
Alyssa’s young son, Waylon, survived the initial collision but suffered critical injuries. Emergency responders transported him to Norton Children’s Hospital in Louisville for treatment. Despite those efforts, the little boy later died from injuries sustained in the crash. Police said he had been properly secured in a car seat in the rear passenger area of the vehicle.
The loss of Alyssa and her son has made the crash especially devastating. A mother and her young child who should have had years of memories ahead of them instead became victims of a collision that investigators say may have involved impaired driving.
Police said Middlebrooks was traveling against traffic for reasons that remain unknown. Investigators believe alcohol consumption by Middlebrooks likely played a role in the crash, although toxicology results were still pending. Authorities have not yet released a final determination regarding the circumstances that caused him to enter the southbound lanes.
The crash brought a major emergency response to I-65. The Indiana State Police Crash Reconstruction Team was requested to assist with the investigation, while other local emergency agencies also responded. The southbound lanes near Seymour remained closed for approximately four hours as investigators documented the scene and crews worked to clear the wreckage.
For Alyssa’s loved ones, the tragedy represents the loss of a young mother whose life was cut short alongside that of her little boy. Waylon, only one year old, had his entire childhood ahead of him before the fatal collision ended his life.
As investigators continue working to establish exactly what happened, the pending toxicology results could provide additional information about whether alcohol contributed to Middlebrooks’ decision or ability to drive. Officials have emphasized that the investigation remains ongoing.
The deaths of Alyssa Osborn and her son Waylon leave behind a profound loss for their family, friends and everyone affected by the tragedy. Their lives were taken in an instant on an Indiana highway, leaving loved ones to mourn a mother and child who should have had many more years together.
The community now remembers Alyssa and Waylon as victims of a devastating wrong-way crash while investigators continue seeking answers about the circumstances that led to their deaths.