Last week, Deputy Kenny Riley became the longest-serving non-elected law enforcement officer in Daviess County. Celebrating 31 years of service, Riley is a well-known figure in the community and in the courtroom where he has served as a security officer for the past several years.
When asked what’s kept him in the profession for so long, Riley said the answer was pretty simple.
“I really enjoy the job,” he said. “I especially loved it when I moved into the courts system because I’ve gotten to meet so many people.”
Riley recently turned down a federal security job in Evansville, Ind., to continue his role at the Morton J. Holbrook Judicial Center. He was hired for the Indiana position but said he decided against commuting to work every day and, when it came down to it, he really enjoyed working in Owensboro.
In 1989, Riley was hired on at DCSO as the youngest deputy they had on staff. He was 22 at the time and the only Black deputy the Sheriff’s Department had on the books. For nine years, it would remain that way, he said.
“You feel like a trailblazer, but then sometimes it’s kind of like you’re the token [Black deputy],” he said. “I think and hope they’ll hire a couple more African Americans there. They’ve had a couple others [rotate in and out] over the years.”
Several honors and recognitions have been bestowed upon Riley over the years, and he also graduated from Leadership Owensboro and Leadership Kentucky.
Riley also served as the president of the NAACP for a time and is also a Methodist minister at Barnes Chapel in Beaver Dam United Methodist. He also worked as a patrol deputy and K-9 officer for DCSO in the past.
When David “Oz” Osborne was shot in the line of duty, Riley became his replacement on the administrative side of the job.
And though Riley said he enjoyed all of those positions, working as a security officer in Daviess Circuit Court has taught him all about the ins and outs of the courts system, describing the job as one where “you see everything happen.”
“The system is flawed, but you see that the system is there to help people,” he said. “I know everyone down there. I’m friends with all those people.”
Self-described as having been given the “gift of gab,” Riley said he was blessed to serve his community in a positive, meaningful way that helped so many people going through difficult times.
“I’m there for security, not to be the judge. Sometimes making things go smoothly is just being there for people,” he said. “When I was being interviewed for the federal court security position in Evansville, they were very impressed with my skills and knowledge. That’s because the Sheriff’s Office training is second to none.”
As for the future, Riley said he’d likely stay on at DCSO for a few more years. Others have asked him if he’d consider running for office after retiring. He said there was a “distinct possibility” of that happening.
