Jay Lewis Wolff was born December 31, 1933, in the Bronx, New York, and moved to Washington, D.C., with his parents at the age of 12. His undergraduate and graduate studies were completed at Georgetown University and he graduated in 1958 with a Doctor of Dental Surgery degree. After service in the Air Force, he returned to the Washington, D.C., area and practiced dentistry for 30 years in Oxon Hill, Maryland, before retiring to Naples, Florida, to begin several years of leisure and travel, also becoming a top club-level tennis player. A second career as a destination history and culture lecturer on luxury cruise ships began after his appearance in 1998 on the History Channel, based on a magazine article about Charles Ponzi, published by an imprint of American Heritage magazine. He lectured worldwide from then until three weeks before his death on June 28, 2025.
Jay is survived by his wife of 70 years, Carol, as well as daughters Maggie and Diana, grandchildren Remy, Russell and CJ, and great-granddaughter Maisy Jane.