Bob was born in Chester to Robert Sheppard Sr. and the former Gertrude Brown. At Swarthmore High, he excelled in basketball and football, and tennis, a sport he played well into his 70s.
In 1947, he married Louise Wood, of Media. They moved to St. Paul, Minn., in 1959.
Bob was a manager and executive for 27 years with the St. Paul Companies, an insurance firm that became St. Paul Travelers after merging with Travelers Property Casualty Co. in 2003. He later became executive vice president of American Hardware Insurance Co., in Minnetonka, Minn., until retiring in 1992.
Bob was a devoted family man and someone who enjoyed civic activities, including working with Habitat for Humanity and the YMCA.
"He was known as a man of enormous generosity, kindness and patience, who brought much love and joy to his family and friends with his love of life, sense of wonder, his wisdom, his delicious Sunday brunches and his loving smile," his family said.
Besides his wife, he is survived by a son, Rob; a daughter, Judy Segal; three grandchildren and three great-grandchildren.
Services: Were Nov. 19 in Maine.
Donations in his memory may be made to the Asheville Area Habitat for Humanity, 33 Meadow Rd., Asheville, NC, 28803, or the Mid-Coast Presbyterian Church, Box 211, Topsham, ME.