The Scottsburg, Indiana, community is mourning the heartbreaking loss of 31-year-old Alyssa Osborn and her 1-year-old son, Waylon Osborn, who died following a devastating wrong-way crash on Interstate 65 near Seymour.
The fatal collision occurred early Sunday morning, August 23, 2026, in Jackson County, approximately one mile south of Seymour. Indiana State Police 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 Alyssa Osborn.
Both Alyssa and Middlebrooks sustained fatal injuries and were pronounced dead at the scene.
Waylon Osborn Dies After I-65 Crash
Alyssa’s young son, Waylon, was properly restrained in the rear passenger seat of the Ford Escape when the collision occurred.
Although Waylon survived the initial crash, he suffered critical injuries and was transported to Norton Children’s Hospital in Louisville. He later died from injuries sustained in the collision.
His death made an already devastating crash even more heartbreaking for the Osborn family and those who knew them.
What Happened in the I-65 Wrong-Way Crash?
According to Indiana State Police, the crash was reported shortly after 2:30 a.m. Sunday on southbound I-65 near the 48-mile marker.
Investigators determined that Middlebrooks was traveling north in the southbound lanes for reasons that remained unknown. His Jeep then struck Osborn’s Ford Escape head-on.
Police said they believe alcohol consumption by Middlebrooks likely played a role in the crash. Toxicology results remained pending, and the investigation was ongoing.
The southbound lanes of I-65 were closed for approximately four hours while investigators reconstructed the collision and crews completed the cleanup.
Remembering Alyssa Osborn
Alyssa Osborn was 31 years old and lived in Scottsburg, Indiana. Her sudden death has left loved ones confronting the devastating loss of a young mother.
Publicly verified biographical information about Alyssa remains limited at this early stage. Her family and friends are the best sources for details about her personality, accomplishments, interests and the memories she leaves behind.
For those who knew Alyssa, her life will be remembered not only through the circumstances of her tragic death but through the relationships she built and the love she shared with her son and family.
Remembering 1-Year-Old Waylon
Waylon Osborn was only one year old when his life was tragically cut short.
His death following the I-65 collision has brought additional sorrow to a family already coping with the loss of Alyssa. The circumstances of the crash underscore the devastating consequences of a wrong-way collision on a busy interstate.
Waylon’s family and loved ones will carry his memory forward as they grieve the loss of a child whose life ended far too soon.
Investigation Into the Fatal Crash
The Indiana State Police Crash Reconstruction Team is investigating the collision with assistance from local law enforcement, emergency medical personnel, fire departments and the Jackson County Coroner’s Office.
Authorities have stated that toxicology testing is pending. No additional conclusions about the circumstances of the crash should be drawn until the investigation is completed.
Obituary and Funeral Arrangements
At the time of this report, official funeral and memorial arrangements for Alyssa Osborn and Waylon Osborn had not been independently confirmed.
Family members may later announce visitation, funeral services, memorial information or a celebration of life. Those announcements should be treated as the authoritative source for arrangements.
The family deserves privacy and compassion as they cope with the extraordinary loss of a mother and her young son.
A Community in Mourning
The deaths of Alyssa and Waylon have left the Scottsburg community grieving following one of the region’s most devastating recent roadway tragedies.
Their deaths are a painful reminder of the unpredictable dangers created when a vehicle travels the wrong way on a major interstate.
As the investigation continues, family, friends and community members are left to remember Alyssa and Waylon and to support one another through an unimaginable loss.