Robert “Bob” Olshen Caldwell, 85, of Stephens City, VA, passed away Friday, December 26, 2025, at Inova Fairfax Hospital.

Mr. Caldwell was born in 1940 in Chico, CA, son of the late John P. Caldwell and Bertha Caldwell Cowden. He attended the Academy of the New Church in Bryn Athyn, PA, and graduated from the University of Montana in 1963, earning a bachelor’s degree in economics. Mr. Caldwell was a retired veteran of the United States Air Force, achieving the rank of Lt. Colonel. He was awarded the Distinguished Flying Cross for his extraordinary achievement while participating in aerial flight during the Vietnam War. Mr. Caldwell flew the F-4 during his service in Vietnam, and his final flight was in the F-111. He was only the fifth pilot to earn Iron Man status for achieving 3,000 flight hours in the F-111. He retired from the Air Force in 1987. He was a member of the Air Force Association and the 20th Tactical Fighter Wing Association, and he attended Opequon Presbyterian Church.

After his service to his country, Mr. Caldwell was an IT Director at Rivkin Radler Law Firm, retiring in 2010. He enjoyed his time in retirement reading, learning how things worked and how to fix them, helping his wife in the garden, supporting her activities with the garden club, painting class, volunteering at the Belle Grove Historic Plantation, traveling to see his family, and spending time with his children and grandchildren.

He was the devoted husband of Kay Kintner, whom he married in 1987 in Port Washington, NY. He was the love of her life.

He was a wonderful husband, father, and grandfather—a beautiful person and a fine man in every way. He was gentle, kind, patient, funny, and loyal, with a strong character and a generous spirit. Everyone who knew him agreed. He was an epic storyteller, had a great sense of humor, and was good at everything he did. He was the best of men and will be greatly missed.

Surviving with his wife are children Brent Caldwell (Suzie) of Bellingham, WA, Teri Caldwell Johnson (David) of Cranston, RI, Geoffrey Bogie (Michelle) of Seeley Lake, MT, and Caitlin Bogie Keelin (Cory) of Vienna, VA; grandchildren, Mindi Caldwell, Kara Johnson, Adam Johnson, Renee Caldwell, Maya Johnson, Cavanagh Keelin, and Chloe Keelin; brother, Alan Caldwell (Maggie) of Columbia, MD; and previous wife, Lody Caldwell, of Washington State.

There will be a celebration of life on Saturday, February 14, 2026, at 1pm at Opequon Presbyterian Church in Winchester, VA. Pastor David Witt will be officiating. A time of food and fellowship will follow the service.

Inurnment will occur at a later date, hopefully at Arlington National Cemetery.

In lieu of flowers, memorial contributions may be made in Mr. Caldwell’s memory to the Opequon Presbyterian Church’s Capital Building Campaign, the Belle Grove Historic Plantation, and WETA.