Kenyu Shimabukuro was very sickly as a child. “He wanted to prove to himself that he was strong and able to physically handle being in the military,” a relative stated. Shimabukuro graduated from Hilo High School in 1951, attended vocational technical school and enlisted in the Army National Guard. In 1954 he joined the Marines to make a career in the military. He was described as a quiet person who kept to himself. He enjoyed tinkering with cars and going fishing.

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During his service in Vietnam he became a member of an advisory team to the Vietnamese military. On Aug. 12, 1968, Shimabukuro was fatally wounded in the Quang Ngai Province when his armored vehicle came under artillery fire.