Lt. Col. William Stratton Callaghan, Jr., USAF (Ret.), achieved his Heavenly Wings on April 20, 2026, surrounded by loving friends and family at Vicar's Landing in Ponte Vedra Beach, Florida. He was 89 years old.

 Bill was born on December 8, 1936, in Brooklyn, New York, to William Stratton Callaghan and Margaret Cook Callaghan. He grew up in Tenafly, New Jersey, though his childhood was shaped by his father's military service — first during World War II and later when recalled by the Air Force for Korea — taking the family to posts across the country. Bill followed in his father's footsteps, graduating from Fishburne Military Academy before entering the United States Military Academy at West Point, where he was a member of the Class of 1959. 

Bill's love of flying began at the age of six, when an Air Force flight instructor treated him to a flight that sparked a lifelong determination to become a pilot. Upon graduating from West Point, he embarked on a distinguished 28-year career in the United States Air Force. He earned his silver pilot wings at Craig Air Force Base in Selma, Alabama, and went on to fly C-130 transport aircraft and AC-119G Shadow gunships, including combat operations during the Vietnam War, where he served as a pilot and wing staff officer with Special Operations at Nha Trang and Phan Rang. His career spanned some 17 different postings, during which he served as Squadron Commander of Air Traffic Control and Communications squadrons, a USAF Sea Survival School instructor, and Division Chief at Headquarters Air Force Communications Command. In 1985, he served as Project Director for the England Air Force Base Open House and Air Show, hosting the Thunderbirds before a crowd of 35,000. He retired from active duty in 1987. 

In December 1959, shortly after graduating from West Point, Bill married Mary Therese Guinea. Mary was his steadfast partner through the many moves and demands of military life. After his retirement, they relocated to Dallas, Texas, where Bill attended SMU Dedman School of Law. He was admitted to the State Bar of Texas in 1992 and practiced estate planning and probate law. Mary passed away on March 7, 2007.

 In the years following Mary's passing, Bill devoted time to his investments, his coin and stamp collections, and to reconnecting with old classmates and military friends at reunions around the country. As he began visiting retirement communities and organizing his household with plans to relocate, he came across pictures and mementos belonging to friends and made it a point to return each one. Among them were photographs of a girl with whom he had shared a summer romance during training at Fort Benning while a cadet at West Point in 1956. Though he did not know her married name, Bill's legal training enabled him to trace and return the pictures to her — Evelyn Greason Crosby, by then a widow living in Ponte Vedra Beach, Florida. What began as a simple reconnection blossomed, and in 2013, Bill and Evelyn were married. 

Bill relocated to Ponte Vedra Beach where he and Evelyn lived at Sawgrass Country Club before moving to Vicar's Landing, a retirement community just across A1A, in 2018. They happily divided their time between Vicar's Landing and the Crosby family's summer home in Cashiers, North Carolina. 

Bill is survived by his loving wife, Evelyn; her children, Tod Crosby (Stephanie) and Maria Crosby Pollard (Saint); grandchildren Julian, Eva, and Selby; a most beloved cousin, Alida Ann Weber, and family; and other loved cousins. 

Burial will take place at a future date at the United States Military Academy, West Point. Memorial contributions may be made to West Point, the Members Association Employees Fund at Vicar's Landing Life Care, or the charity of your choice.