Born in West Chester, PA, on December 30, 1928, he was the only son of C. Roland and Carrie Cathrall Pyle.
Roland got his nickname after toddling into his mother’s bridge club game wearing an oversized pair of boots. (He wasn’t known as John until qualifying for Medicare.) Boots helped his father and grandfather on their dairy farm and graduated from Kennett Consolidated High School in 1947, before serving in the Air Force during the Korean Conflict. On September 11, 1954, he wed the love of his life, Ruth Ann Lockard and together they raised five children, in Avondale, PA, Waukegan, IL, Elkmore, MD and Wilmington, DE.
He worked at a variety of jobs, mostly as a salesman, and retired from Limestone Liquors. He was a member of Masonic Lodge #475 in Kennett Square, PA, the Kiwanis of Wilmington, DE and the Methodist Men at Wesley.