Captain William C. Bailey, USNR (Ret.)

Captain William C. Bailey, USNR (Ret.) passed away peacefully at his home in Longwood, Florida on August 27, 2026. A native of Oak Park, Illinois, Bill attended Fenwick High School, where he was a standout athlete in basketball and golf. He graduated from the United States Naval Academy in 1972, proudly serving as captain of the Naval Academy Golf Team.

After graduation, Bill served aboard the USS Kretchmer before earning his naval aviator wings in 1974. Flying the A-7E Corsair, he completed deployments to the North Atlantic and Mediterranean with the "Marauders" of VA-82 aboard the USS Nimitz. The “Marauders” earned the Battle "E" and the Admiral Wade McClusky Award. He later served as an instructor pilot with VA-174, transitioned to the Naval Reserve in 1979, and joined the "Blue Dolphins" of VA-203. During his tenure, the unit earned multiple top squadron honors, and Captain Bailey transitioned to the F/A-18 Hornet before assuming command of the squadron in 1990. Bill cherished the many friendships he made during his Naval career.

In addition to his distinguished military service, Captain Bailey pursued a successful commercial aviation career, flying as a pilot for Eastern Airlines for 10 years, Northwest Airlines for 10 years, and concluding his career with Delta Air Lines until his retirement. At each airline he enjoyed working in the training department in addition to flying.

Outside of his career, Bill was happiest on the golf course, spending time with his family, working in his yard, traveling with his wife, and following the Jacksonville Jaguars. He will be remembered for his unwavering integrity, his kind nature towards everyone he met, his deep devotion to his family, and, most of all, his wonderful laugh.

Bill is survived by his beloved wife of 49 years, Katherine; their children, Brian (Jackie) and Allison Grant (Jeffery); and their seven cherished grandsons: Brody, Holden, Reed, Ian, Declan, Ryan, and Wesley. He is also survived by his siblings, Jack (Emma), Robert (Shelly), Tim (Anne), Dan, and Mary Beth Catenzaro (Frank).

A Mass will be held on Friday, September 4, at Annunciation Catholic Church, 1020 Montgomery Road, Altamonte Springs, FL 32714, at 10:00 AM. Interment with military honors will take place at the Jacksonville National Cemetery at a later date. Friends are welcome. In lieu of flowers, the family kindly requests that donations be made to the Pancreatic Cancer Action Network or a charity of your choice.