Chester Fleming

Chester Fleming of Mossy Head Florida passed away November 29th, 2025 after a four-year battle with Acute Myeloid Leukemia.

Chester was born in Ludlow, Massachusetts to Jerry Fleming and Roberta (Foley) Fleming. He was raised in Kansas City, Missouri and Holt Missouri with brothers, Gene and Sean, and sister Roxanne (Fleming) Wing. He is survived by his wife of 5 years, Ramona S. Tryon, his daughter Joy H. Fleming, his sister (Rocky), and numerous friends and “Air Force Kids” who will miss his wisdom, support, sage advice and dark sense of humor.

He signed up for the Air Force in the fall of 1974 and went to Basic training in June 1975.
1975 – 1979 – 20th SOS at Hurlburt Field as crew chief on H-1N and C/HH-3E’s.
1979 – 1982 – Det. 1, 33rd ARRS at Clark AB, RP. as crew chief on C/HH-3E.
1982 – 1984 – 1550th at Kirtland AFB, as crew chief/expediter on C/HH-3E.
1984 – 1985 – 38th ARRS as crew chief on CH-3E.
1985 – 1987 – 31st ARRS at Clark AB, RP. as crew chief/phase dock chief on C/HH-3E.
1987 – 1992 – 20th SOS at Hurlburt Field with 30 plus H-53s of all types (no two alike) crew chief/expediter/Flt chief.
1992 – 1994 – SMOTEC/18th FTS structural modification flight test program (50K test) with 994 and OT&E FSD V-22s.
1994 – 1996 – HQ. AFSOC LGMW MH-53J/M and FSD V-22 program manager. (This job sucked so bad he retired!)

In his words he was a “mere helicopter mechanic”. While in the Air Force he earned 2 Associate degrees, a Bachelor degree and most of a Masters in Aeronautical Engineering. His love of mechanical things led him to rebuild motorcycles from parts in boxes. Usually on a kitchen table. He followed the military up with time working as a Test Engineer on Eglin AFB. He started his own business fixing small engines and generators. Fully retiring in 2018.