Flagg spent 25 years in the Army and 20 years as an educator, continuing to serve others even after retirement. He died Sept. 24, 2025.

“Colonel Jeff Flagg was always someone who cared for the people around him,” Randall Howard said. “If there were a way to help someone who needed it, he would do it, no questions asked. He knew the value of people. He treated everyone the same and shared his experiences with others in hopes he could help them find some peace themselves, whether it was veterans, teachers or students.”

Howard said Flagg’s willingness to talk about difficult moments in his life helped many people.

“Understanding the value of people is something I will always remember about him,” he said.

Flagg’s expertise on the Vietnam War made him a sought-after resource among educators. Colleagues at Omaha Burke High School regarded him as one of the strongest primary sources on the war in the area. Students were captivated by his presentations because of his engaging storytelling and the way he brought history to life.

“He was a phenomenal storyteller,” Howard said. “His stories would hold people’s attention for hours on end. The way he engaged with others while telling his stories was something to admire. I learned so much from him about Vietnam, but also several life lessons. I will always remember his character, integrity and kindness toward everyone. I will miss him.”

Each year, when Burke students studied the Vietnam War era, they heard Flagg’s firsthand accounts, often the highlight of the unit. His presentations offered a unique perspective, complete with photographs, anecdotes and vivid descriptions of wartime conditions. As a decorated veteran, he contributed history on a deeply personal level.

“He made an impact because he told his stories, and I think that’s really neat to remember,” Barbara Boltinghouse said. “We always hear about history, but these were his stories, and he made it come alive.”

Boltinghouse said students gained both historical perspective and respect for military service.

“He told the kids exactly what it was like and how he felt,” she said. “He told good times. He told some bad times. I think the kids got a view of what was happening in history, but also left with a very good impression of the military and the people who serve our country.”

Flagg’s connection to Omaha Burke began when he took charge of the school’s JROTC program. Under his leadership, enrollment doubled and the program’s achievements grew. His work helped build a strong foundation, eventually leading to his role as director of JROTC for all Omaha Public Schools. He served in that position for three years before retiring alongside his wife.

“He personally made an impact on me when I met him my freshman year,” Samantha Sikes said. “He was telling us about his experiences and showing us pictures. It became a yearly thing where I would see him and talk with him at events. He watched me grow in the program as I improved and learned new things.”

Sikes said his guidance went beyond the classroom.

“Honestly, just being a good instructor, he helped me realize different things about JROTC and about being a good person,” she said.