Leonard P. Cheshire Jr. Commander USN (Ret.)

Leonard P. Cheshire, Jr. (Lenny), a long-time Virginia resident, died of kidney failure at The Jefferson, 900 N. Taylor St., Arlington, Virginia, on July 29, 2024. He is survived by a sister, Jeanette McAllister; a brother, Wayne Cheshire; close friend, Alex Oporto, who was like a son to Lenny; and numerous nieces and nephews who adored him. His sister, June Dupree preceded him in death.

Lenny was born on July 31, 1937, in Wellborn, Florida. When he was four years old, his family moved to Gainesville, Florida, where he lived until leaving home at the age of 22 to join the U.S. Navy. He graduated from Gainesville High School in 1955 and then entered college. He received a Bachelor of Industrial Engineering from the University of Florida in 1959 and a Master of Business Administration from The George Washington University in 1973.

After graduating from the University of Florida, in February 1960 he attended the Navy’s Officer Candidate School at Newport, Rhode Island. Following completion of OCS in June 1960 he was assigned to an aircraft carrier, the USS Intrepid (CVA-11). In February 1963, Lenny volunteered for submarine duty and attended Submarine School at New London, Connecticut. He subsequently served on the submarines USS Harder (SS-568), USS Threadfin (SS-410), USS Sea Cat (SS-399), and the USS Dogfish (SS-350), on which he served as the Executive Officer.

Following many years of sea duty, in 1972 the Navy sent Lenny to graduate school at The George Washington University, where he earned a Master of Business Administration Degree. Using his MBA and degree in Industrial Engineering, Lenny provided independent cost estimates for Naval weapons systems going through the development and procurement process. He retired from the Navy in 1980 with the rank of Commander.

Between 1980 and 1986 Lenny worked with firms having contracts with the U.S. Navy. In the fall of 1986 he accepted a civilian position with the Naval Center for Cost Analysis, where he worked on many procurement projects until retiring from the Federal Government in 2002.

During his military service and throughout his years as a civilian employee and retiree, Lenny traveled extensively abroad and in country.