Cynthia Jean Bailey

Cynthia Callaway Bailey, a beloved wife, mother, grandmother, sister, counselor, and friend, lived a life defined by compassion, adventure, and unwavering love for others. Born on March 27, 1947, in Hot Springs, Arkansas, she was the first child of Stell and Jodie Jean Callaway. When her sister arrived, Cynthia was given the honor of choosing her name and proudly selected Polly Ann, beginning a bond that would last a lifetime.

Cynthia grew up and attended school in Arkadelphia, Arkansas, a town she loved so deeply that she chose to attend Henderson State University there. It was at Henderson that she met Paul Bailey, a football player who swept her off her feet in the university cafeteria. They married while still students and built a partnership filled with laughter, devotion, and shared adventures. Paul’s military service took them to Germany and Italy, and later to various posts across the United States, including Fort Knox, Kentucky, where their son John was born, and Fort Rucker, Alabama. While Paul served in Vietnam, Cynthia remained in Arkansas with their daughter Allison.

Cynthia earned a master’s degree in counseling and worked as an elementary school counselor and later as a school psychologist in Texas and with the Lakeside School District in Arkansas. She and Paul eventually returned to Hot Springs to care for their aging parents. An enthusiastic traveler, Cynthia explored Europe, Southeast Asia, Australia, Alaska, Hawaii, and the Caribbean with her husband, children, and grandchildren, creating cherished memories. A lifelong animal lover, she volunteered with Paws and Claws and rescued her beloved dogs Tanner and Lily, while caring for many others at the family farm.

Diagnosed with Parkinson’s disease, Cynthia faced the challenge with characteristic determination and became an active participant in Rock Steady Boxing. Above all, she was known for her deep compassion, quietly helping children and adults alike with food, clothing, encouragement, and unconditional love. She was preceded in death by her husband of fifty years, Paul Bailey. She is survived by her daughter and son-in-law, Allison and Brad Dierlam, and their children, Carter and Ella; her son and daughter-in-law, John and Tess Bailey, and their children, Victorine and Justice; her sister, Polly Ferguson; her nieces Bonnie and Katherine; and her great-nieces, Kinley, Aida and Amelia. Her family will forever cherish her generous spirit and the immeasurable love she gave so freely.