Bob Hess, a proud veteran of the United States Air Force, dedicated husband, father, grandfather, great‑grandfather and friend passed away on 5 August 2023 in Colorado Springs surrounded by family. The son of Chief Warrant Officer (CW‑4) Clarence and Genevieve Hess, Bob grew up as an Army brat in Baltimore, Maryland, Munich and Heidelberg, West Germany and Fort Knox, Kentucky.  He was born 9 September 1934 in Washington, D.C. and graduated from high school in West Germany, where he excelled at sports.  He was highly recruited to play college basketball; unfortunately, he contracted and beat polio when he was only 18.  While this setback cut short his basketball career, it opened the door for the Air Force and a lifetime of Service.  

On 28 January 1954, he reported to Lackland AFB to begin Aviation Cadet training. He was commissioned a 2Lt and awarded Navigator Wings at Harlingen AFB on 22 March 1955.  Bob received a second Aeronautical Rating as a Radar Observer at Moody AFB on 31 October 1955. While at Moody AFB, he was interviewed by the newly designated Vice Commandant of Cadets, Colonel Ben Cassiday, who selected him to serve as an Air Training Officer at the fledgling Air Force Academy. 2Lt Bob Hess reported to Lowry AFB on 15 May 1956 as the youngest of 134 ATOs, where he helped establish the highest standards, customs and traditions for cadets that set the strong foundation for every single graduate of the Long Blue Line.

Bob earned his 3rd Aeronautical Rating and Pilot Wings on 22 November 1958 at Webb AFB, where he also served as an Instructor Pilot. During his flying career, Bob flew 6,002 hours in aircraft including the T‑29, B-25, T‑34, C-47, T-28, F‑89, T‑33, T-37, T-38, T-39 and C-123.

During his service to the nation, Bob served with distinction in South Vietnam, Korea and bases across the United States.  In Vietnam, he spearheaded testing on night, low-level, blacked out paradrop tactics in support of US Special Forces in Southeast Asia using modified C-123s.  As the Director of Plans and Programs at USAFA, he wrote and executed the plan that brought women to the Academy in the Class of 1980.  Also, while at USAFA, Bob served as Gen Chappie James Chief Pilot and flew Bob Hope to the Academy to perform one of his famous USO shows.  In his last assignment, he helped stand up US Central Command in the aftermath of the Iranian Hostage Crisis.  Following his military career, Bob continued to serve his community for 22 years as a realtor, where he won Colorado Realtor of the Year honors for Coldwell Banker and was Vice President of Sales and a Distinguished Service Award winner for Moore and Company.

Bob is survived by his wife of 66 years, Kaye Hess; three children, Derek (Barb), Daren (Jayne), and Diana (Ron); eight grandchildren, Austin (Kat), Amanda (Rob), Alex (Sami), Rob (Jordan), Joe, Mike, Seiler (Claire), and Cullen; and two great-grandchildren, Holly and Mei.  His loved ones will remember his dedication to duty, leadership, integrity, and love of his large close-knit family.  In lieu of flowers, the family requests you consider donations to the Parkinson’s Foundation, the American Diabetes Foundation, or the Friends of the Library at the Air Force Academy.

A service honoring the life of Colonel Robert C. Hess will be held at the United States Air Force Academy Cemetery on 31 August 2023 at 1000.  A Celebration of Life Reception at the Falcon Club at his beloved Air Force Academy will follow immediately after his interment.

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This Obituary Has 10 Condolences

  1. It was an honor to have known Colonel Robert Hess

  2. Dear Diana and family, reading the accounts of your grandfather and his remarkable life. You must be so proud and I know you are. I’m sorry for your loss of this great man. He lived a great lives and served his country well.

  3. Prayers and condolences to the Hess family. Col. Hess was an impressive man with such a distinguished career. We are blessed to have met him.

  4. The Buckley SFB military Retiree Activities Office (RAO) would like to offer our sincere condolences and our gratitude for Col Hess’ distinguished service to our country in the Air Force. If you would like help with any matters related to casualty assistance, Defense Finance & Accounting Service, Survivor Benefit Plan (SBP), Veterans Affairs (VA), etc. you can contact our office on Buckley SFB at 720-847-6693 or The RAO is staffed by volunteers, all military retirees themselves, and our sole purpose is to provide assistance to any military retirees and surviving spouses/family members with anything related to their military service and/or benefits, in particular during difficult times such as this. We are deeply sorry for your loss.

    Steve Young
    Lt Col, USAF, Ret
    Director, Buckley SFB RAO

  5. On behalf of Major John R. Englehart, USAFA ATO, USMA 1953, (deceased) and Ellen Englehart, we extend our condolences on the loss of a great man. A pillar in the ATO community, his willingness to “scribe” for all is a testament to his lifelong commitment to service. The Long Blue Line lives on in the sons and daughters of these pioneers. Godspeed to Bob Hess and tailwinds to Kaye as the entire Hess Family journeys onward. Robert Englehart, USAFA 1983.

  6. I will surely miss talking to my brother and remembering the advice he gave me whenever I needed it.

  7. My utmost respect goes to a man with such a distinguishing and honored career. Heartfelt condolences for the family and friends of Colonel Hess.

  8. Then Lt Hess served as one the Air Training Officers (ATOs)–stand-ins for a yet to be available upper class–during our early training at the U. S. Airforce Academy. He is remembered by those of us who had the honor of serving under him as one of the most considerate and helpful among the ATOs. He was always firm but fair, and he had compassion for those who struggled during the transition from civilian to military life. The example he provided served as a superior role model to us all. Our thanks to him for putting us on the right path, and our condolences go to his family and fellows.

  9. I can’t even begin to express my heartfelt condolences to Kaye and to Bob’s wonderful and loving family. It was an honor to have been a Realtor alongside “The Colonel” for many years. He blessed so many people with his passionate mentoring, fun, laughter, jokes, and above all . . . his incredible integrity! He will truly be missed by many but never forgotten. God Bless the Colonel!

  10. How fondly we recall the ATOs that met us and introduced us to the Academy in those years long ago in time but instantly recalled in memory.

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