James "Jim" Winn
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James "Jim" Winn, beloved husband, father, grandfather, and friend, died at home on March 22, 2022 following a series of illnesses that took more and more of his health. Jim was known by all for his warm, upbeat personality, a genuine smile for every greeting, and a distinctive style for almost everything he did. Around children, he was pure joy, entertaining them with stories that invariably included rollicking vocals and delightful facial expressions. A truly multi-faceted individual, Jim was a musician, a businessman, an aviator, a military officer, and an athlete. Somehow, he balanced all these roles, responsibilities, and activities with a rich family life.
Jim's early childhood years were in Irvington and Leitchfield, KY, and his high school years in Lake Worth, FL. He went to Eastern Kentucky University on a full music scholarship, double majoring in music (vocals and low brass instrumental) and business. While at Eastern, he played varsity tennis and was a member of Army ROTC. Upon graduation in 1955, he was commissioned as an Army officer and initially served in Artillery. He developed an interest in aviation and attended a series of flight schools. During fixed wing training in San Marcos, TX, Jim met Elizabeth Pitts Kyle. He quickly and resolutely chose her to be the woman with whom, together, they would build a family and a life. They were married for 63 years.
In 1960, they moved to Campbellsville, KY. Jim left active duty and joined his brother as a partner in Winns' Store for Men, a clothing store. Outside the business, Jim was active in church choir, as a volunteer Minister of Music for various churches in the area, as a leader in Community Concerts, as a Rotary Club member, and as an athlete playing tennis, golf, volleyball, handball, and wicked fast ping pong. He also served as an aviator in Kentucky National Guard, flying both fixed and rotary wing aircraft.
In the early 1980s, Jim left full time work as a merchant, transitioned to flying helicopters commercially, and moved to Lexington, KY. He continued to be active in his church and a variety of local music ensembles. He flew helicopters for Kentucky National Guard until mandatory retirement at age 60 and flew commercially until age 65.
In retirement, he led a physically and socially active life, taking several memorable trips with close friends and family. He and three of his EKU classmates reconstituted a barbershop quartet from their college days, created a patriotic themed show, and took it on tour for several summers, entertaining at veteran's hospitals and retirement homes.
Jim deeply loved his two children, was proud of their accomplishments, and the individuals they grew into. His grandchildren were endless sources of joy, and he was proud of their accomplishments and their aspirations. During his last two years, Jim often talked about how fortunate he had been in life. Among the most frequent expressions of gratitude was the strength and closeness of his marriage and the vigilant, compassionate, and tender care he received from his wife as his health declined.
James Robert Winn was born on June 10, 1933, in Irvington, KY. He is survived by his wife, Elizabeth Pitts Kyle Winn, his brother Ted Winn (Mary Alice) of Lawrenceburg, KY, his son James Kyle Winn (Angie) of Louisville, KY, his daughter Holly Elizabeth Winn Brown of Louisville, KY, and two grandchildren, Clayton Kendall Brown and Charlotte Elizabeth Winn, both of Louisville, KY. He was preceded in death by his parents, Theodore S. and Helen Elizabeth Smith Winn, a brother Charles Winn, son-in-law Kevin Kendall Brown, and granddaughter Elizabeth Holloway Brown. Kerr Brothers - Harrodsburg Rd., Lexington, KY is handling the arrangements.