Theosco Middlebrooks and Alyssa Osborn died in a head-on collision on I-65 near Seymour, Indiana.
Theosco Middlebrooks and Alyssa Osborn both died in a head-on collision on I-65 near Seymour, Indiana, early Sunday morning. The 51-year-old Middlebrooks was driving a 2005 Jeep Liberty northbound in the southbound lanes when he struck a 2023 Ford Escape driven by 31-year-old Alyssa Osborn. While Middlebrooks and Osborn died at the scene, Osborn’s 1-year-old son, Waylon, was critically injured and later died at a hospital. Police noted that the child was properly restrained in a car seat during the impact. Investigators believe alcohol consumed by Middlebrooks likely played a role in the crash. The investigation remains ongoing as toxicology results are pending. Southbound lanes of I-65 were closed for approximately four hours to facilitate the investigation and cleanup.