Following service in the South Pacific in World War II, Stewart completed his degree in English at Willamette. He started his teaching career at Myrtle Creek High School, but returned to North High in 1951 where he was an English teacher and counselor. In 1964, he became an assistant principal, holding that position at North, South, McNary, and Sprague. A beloved educator, Stewart was a lifelong scholar and poet. He passed away in 1910 at the age of ninety.