A 5'11" guard/forward, Armstrong starred at Central High School in Fort Wayne, Indiana, where he reached two state championship games while leading his team to a 50–6 record. In the late 1930s and early 1940s, Armstrong attended Indiana University, earning All-Big Ten Conference honors during his junior year. He then played, and briefly coached, for the Fort Wayne Zollner Pistons professional basketball team (today's Detroit Pistons). In 1943, he was named the World Professional Basketball Tournament's Most Valuable Player. He was inducted into the Indiana Basketball Hall of Fame in 1980.
He was head basketball coach at Wabash College in Crawfordsville, Indiana, for two seasons. His record in 1951–52 was 10 wins and 10 losses. His record in 1952–53 was 9 wins and 10 losses.

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