Leo Osman Riley

Leo Osman Riley, a cherished son, brother, husband, father, and proudly known as Grandaddy, passed away on October 9, 2025 in Glasgow, Kentucky. He was born on May 22, 1940, in Barren County, Kentucky to the late Stanley Riley and Charlotte Louise Royal Riley. Leo's life was marked by love, dedication, and a profound sense of family.

He graduated in 1958 from Bristow High School in Warren County, Kentucky and attended Western Kentucky University, majoring in Engineering. Leo began his career in farm equipment sales in 1960 with Western Kentucky Tractor in Bowling Green, Kentucky, where he sold Ford tractors and began a career that would span many decades.He spent several years in Russellville with Western Kentucky Tractor before a stint opening company stores for J.I. Case Company. He later spent time as a Hesston manufacturer factory representative traveling the midwest. In 1980 he was hired to manage Watkins Service in Abilene,Texas, bringing Kubota tractors to West Texas. He ended his career with Industrial Trucks of Dallas,Texas before opening Riley Pecan Company in Abilene, Texas. He retired to the farm in Center,Kentucky in 2019 where he spent his final days.

Leo was preceded in death by his wife of 64 years, Shirley. They cherished their time together,enjoying travel and, most of all, time with their family. They loved watching their grandchildren grow, who were truly their pride and joy.

He is survived by his beloved children, Leo Riley Jr., John Hull Riley (Lou Ann), and Autumn Ellen Redwine (Monty). Leo took great pride in his role as a father and continued to nurture those familial bonds throughout his life. He was also a devoted grandfather to Rebekah Button (Brock), Rachel  Martin (Michael), John David Riley (Jenny), Kacy Redwine (Chelsea), and Lacy Harvey (Sean). His family grew further with the addition of his bonus grandchild, Marissa Northrup (Caleb), and twelve great-grandchildren: Alexis, Bryce, Emma Kate, Owen, Jackson, Lindley, Patrick, Sadie, Kyler, Kieran, Liam, and Ace. He also leaves behind a special cousin Tabitha Huffman, as well as several nieces and nephews who will remember him fondly.

Leo's legacy lives on in the hearts of these loved ones, who will remember him for his kindness,wisdom, cheerful sense of humor, and unwavering support.

In addition to his parents and wife, Leo was preceded in death by his siblings: Stanley Riley Jr., John Davis Riley, Dr. Cordell Riley, Wayne Riley, Russell Riley, Mary Keown, and Perry Riley. The love shared with his siblings remains a treasured part of Leo's story. The childhood bonds developed among the brothers shaped their lives and was an enduring part of their legacies.

The family extends their heartfelt gratitude to Leo and Shirley’s devoted sidekicks, Angelina and Miriam, who became more than caregivers, they became family. Their gentle care, loving presence, and shared laughter brought joy and comfort to Leo and Shirley each day.

Visitation services will be held on October 17, 2025, from 5:00 PM to 8:00 PM at A.F Crow & Son Funeral Home. A graveside service will follow, on October 18, 2025, at 12:00 PM, at Hiseville Cemetery. There will be a reception to follow the service at Willow Oaks Golf Club in Glasgow.

Leo Osman Riley, Grandaddy, will be remembered as a man who brought joy to all who knew him. His gentle spirit and loving nature will forever remain in the hearts of his family and friends. 

The family would like to give a special thank you to the staff at Shanti Niketan Hospice Home in Glasgow.