Alyssa Osborn and Waylon Osborn Obituary, SCOTTSBURG, Ind. — Alyssa Osborn, 31, of Scottsburg, Indiana, and her 1-year-old son, Waylon Osborn, died following a devastating wrong-way collision on Interstate 65 near Seymour early Sunday morning, August 23, 2026.
According to Indiana State Police, the fatal crash occurred in Jackson County, approximately one mile south of Seymour. Authorities said a 2005 Jeep Liberty driven by 51-year-old Theosco Middlebrooks of Louisville, Kentucky, was traveling northbound in the southbound lanes of I-65 when it collided head-on with a 2023 Ford Escape driven by Osborn.
Alyssa Osborn and Middlebrooks both sustained fatal injuries in the collision and were pronounced dead at the scene. Waylon was properly restrained in the rear passenger seat of the Ford Escape and initially survived the crash with critical injuries.
Waylon was transported to Norton Children’s Hospital in Louisville for treatment. He later died from injuries sustained in the collision, adding another devastating loss for the Osborn family and those mourning the crash.
Indiana State Police said the crash was reported shortly after 2:30 a.m. near the 48-mile marker of southbound I-65. Investigators determined that Middlebrooks had been traveling north in the southbound lanes, although the reason he entered the wrong lanes remained unknown. Police said they believed alcohol consumption likely played a role, while toxicology results remained pending.
The southbound lanes of I-65 were closed for approximately four hours as investigators reconstructed the collision and crews completed the necessary cleanup. The Indiana State Police Crash Reconstruction Team is investigating the circumstances surrounding the crash with assistance from local law enforcement, emergency medical personnel, fire departments and the Jackson County Coroner’s Office.
Publicly verified information about Alyssa’s life, career, accomplishments and personal interests remains limited at this time. She is remembered in the available information as a 31-year-old mother from Scottsburg whose life was tragically cut short alongside that of her young son.
Official funeral or memorial arrangements for Alyssa Osborn and Waylon Osborn had not been independently confirmed at the time of this report. As the investigation continues and the family makes arrangements, additional information may be released. The loss of Alyssa and Waylon has left loved ones and members of the Scottsburg community grieving as they remember a mother and her young son and offer compassion to those affected by the tragedy.