Robert Bolen Riley, lovingly known as Bob, passed away peacefully on August 3, 2026, at the age of 96.
Bob was born on July 13, 1930, in Kansas City, Missouri. He attended college, where he majored in psychology, before answering the call to serve his country. In 1952, he joined the United States Air Force and proudly served for four years as a fighter pilot, attaining the rank of Captain. During his military service, he was awarded the Korean Service Medal, the United Nations Service Medal, and the National Defense Service Medal in recognition of his dedication, courage, and honorable service.
Following his military service, Bob embarked on a distinguished career as a commercial airline pilot with American Airlines. It was during this chapter of his life that he met the love of his life, Evelyn Riley. Together they built a wonderful life and raised their family in Warren and Ridgefield, Connecticut, sharing many happy years filled with love, laughter, and lasting memories.
Family was always at the heart of Bob’s life. He and Evelyn were blessed with two daughters, Cathy and Sharon, and he took great pride in watching his family grow through the generations. Bob was preceded in death by his beloved wife, Evelyn, and his daughter, Sharon Riley, who passed away in 2021. He is survived by his daughter, Cathy Fitzpatrick and her husband, Larry; three grandchildren; and seven great-grandchildren, all of whom brought him immeasurable joy and pride.
Bob will be remembered for his quiet strength, unwavering integrity, deep love for his family, and steadfast commitment to serving others. Whether soaring through the skies as a fighter pilot and airline captain or spending treasured time with those he loved, he lived a life marked by dedication, humility.
Cathy, Larry, Courtney and Ryan,
My deepest condolences. When Matt told me about Pop Riley’s (as Matt calls him) passing I was deeply saddened. My heart goes out to you all and I pray that you all will find peace and comfort during this difficult time.
It warms my heart when I hear that you all have stayed in touch with Matthew. He loves you all deeply.
With deepest regards,
Phil
I have nothing but great memories of Bob. From the cookouts in Randolph, gatherings in Milton or New Hampshire, Bob always had a wonderful smile. I am certain he will be missed.
I was very saddened to hear about the passing of Uncle Bob. So many wonderful memories with him, Aunt Toots, Cathy and Sharon I will always cherish. Please know that Scott and I are sending love and hugs to the entire family. Hoping you can all visit your Ohio family again soon. 🙏❤️
Bob was such a kind man who always had a pleasant word for everyone. His quiet presence will be missed at the FL condo building by all. Our sympathies to you and your family.