The Scott Clark Washington County Herald Newspapers and The Outlook Guide

08/23/2026

August 23, 2026*

Wrong Way Crash on I-65 Near Seymour Claims Three Lives

Early this morning, a two-vehicle crash involving a wrong way driver claimed three lives on I-65 near Seymour, in Jackson County, Indiana.

Shortly after 2:30 am, a caller reported a head on crash on I-65 Southbound just south of the 48-mile marker in Jackson County. The crash occurred approximately one mile south of Seymour. Responding officers quickly determined the crash involved fatalities and requested the Indiana State Police Crash Reconstruction Team to conduct the investigation.

The initial investigation determined that, for an unknown reason, a 2005 Jeep Liberty being driven by Theosco Middlebrooks, age 51, Louisville, Kentucky was traveling northbound on I-65 in the southbound lanes, just south of the 48-mile-marker. Middlebrooks’ vehicle collided head on with a 2023 Ford Escape being driven by Alyssa Osborn, age 31, Scottsburg, Indiana, that was traveling southbound in the southbound lanes.

Tragically, both Middlebrooks and Osborn sustained fatal injuries. They were both pronounced deceased on the scene by the Jackson County Coroner’s Office. The one-year-old infant son of Osborn, Waylon Osborn, who was properly restrained in the rear passenger seat of the Ford Escape, sustained critical injuries in the collision. He was transported to Norton Children’s Hospital in Louisville, Kentucky where he was later pronounced deceased due to injuries sustained in the crash.

The investigation is ongoing. Investigators believe that alcohol consumption by Middlebrooks likely played a role in the crash. Toxicology results are pending.

All southbound lanes of I-65 just south of Seymour were closed for approximately four hours for crash investigation and cleanup.

Both families have been notified.

The Indiana State Police Crash Reconstruction Team was assisted by Troopers with the Indiana State Police-Versailles Post, Seymour Police Department, Jackson County Sheriff’s Department, Jackson County EMS, Seymour Fire Department, Redding Fire Department, Vernon Township Fire Department, and Jackson County Coroner’s Office.

-30- WHEELES

08/22/2026

08/22/2026

Scott County Sheriff’s Deputy graduates from the Indiana Law Enforcement Academy
Scott County - On August 20th, Scott County Sheriff’s Deputy Christopher Smith graduated from the Indiana Law Enforcement Academy, concluding 16 weeks and 649 hours of law enforcement training. The academy, as known by those who have walked the hallways of the facility located in Plainfield, Indiana, is a training complex where citizens wishing to become police officers are molded into what the Indiana Law Enforcement Training Board wishes Indiana Police Officers to be…servants of the people. Long training events, followed by even longer training days, resulted in the certified police officers and deputy sheriffs graduating from the 239th session of the Law Enforcement Academy. The Mission Statement and Core Values of the Academy are as follows…MISSION: As Indiana’s center for law enforcement education, the academy sets and maintains the standard for law enforcement education. We prepare law enforcement personnel for service through continuous and innovative training guided by clear values and respect. CORE VALUES: Professionalism - Perform your job with competence and a commitment to excellence… Accountability - Take responsibility for your work and actions by living up to the highest possible standard… Inclusion - Continuously recognizing the value of everyone’s contribution to our mission… Respect - All are treated with dignity, fairness, and a sense of purpose. Deputy Smith reported for duty at the Scott County Sheriff’s Office immediately following graduation, assuming his role as the School Resource Officer (SRO) at the Vienna-Finley Elementary School. From all of us at the Sheriff’s Office and the citizens of Scott County, welcome on board, Deputy Smith!
NOTE: In the photo below, Deputy Smith is congratulated by Chief Deputy Joe Guarneri and Scott County Sheriff Jerry Goodin.

-30-
Dawson

08/22/2026

08/22/2026

Highlights from the Car Show on the square in Scottsburg Friday evening, August 21 - Staff Photos by Joe Stevens - The Scott County Herald - Amos Publishing LLC

08/22/2026

Scottsburg trails Madison 7-0 at halftime.

Friday Night Football

08/21/2026

🎶Leota Country Frolic Music Lineup! 🎶

We’ll keep spotlighting our amazing musicians (because they deserve every bit of love 💛)… but for everyone who’s been waiting, here’s the full 2026 Leota Frolic lineup straight from the poster!

🎤 Friday, August 28th
5:00 PM – Kayla Griffin
6:00 PM – Jon & Sarah Giddens
7:00 PM – Josh Richards & Brian Allen
8:00 PM – Six Ways to Sunday

🎤 Saturday, August 29th
Noon - Stephanie Anne Music
1:00 PM – Tradesmen Trio
2:15 PM – Bomar & Ritter
3:30 PM – Southern Indiana Cloggers
4:45 PM – Conversations with June
6:00 PM – Sara Swisher
7:15 PM – Dave Campbell Music with Katelynn Brown
8:30 PM – On the House🎡✨

Great music, good times, and all the small‑town charm we love. Bring your people, your lawn chairs, and your Frolic spirit — it’s going to be a weekend to remember!

08/20/2026

RISING SUN/OHIO COUNTY, IN: There's so much going on in Rising Sun/Ohio County, IN, be sure to pencil the events in your calendars! There's more fun things going on during the remainder of August 2026, but we're getting ready for September and October too. Be sure to send your Rising Sun/Ohio County events to [email protected]. Additional listings are on the enjoyrisingsun.com website under the "Events" tab. We're having Fun in Rising Sun/Ohio County!

08/20/2026