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Born in Aberdeen, South Dakota, Barry starred in basketball, baseball, and football in high school in Madison, Wisconsin. He continued his success at Lawrence College in Appleton, later completing his degree at the University of Wisconsin in Madison. He returned to Madison High School to begin his coaching career, and then became the athletic director at Knox College in Illinois from 1918 to 1922, where he also served as coach of football, basketball, baseball, and track.
In 1922, Barry was named basketball coach at the University of Iowa in Iowa City, and also became a football assistant under Hawkeyes head coach Howard Jones, an association which would continue for 15 years at two universities. Barry also coached the baseball team in 1923 and 1924. He led the Hawkeye basketball team to Big Ten Conference co-championships in 1923 and 1926—the first two conference titles in team history. In 1929, he wrote a handbook on the sport: "Basketball: Individual Play and Team Play" that featured University of Iowa players and facilities. He also helped Jones guide the football squad to an undefeated 7–0 season in 1922, winning a share of the Big Ten title—the last for Hawkeyes football until 1956.
In 1929, the University of Southern California in Los Angeles was in need of a new basketball coach, and Jones—at USC since 1925—recommended his old colleague for the position. Barry followed Jones out west, and took over the USC basketball program as well as the baseball team, while also resuming his duties as an assistant football coach under Jones. Barry's Trojan basketball teams won Pacific Coast Conference titles in 1930, 1935, and 1940—along with eight southern division titles between 1930 and 1940—and conference crowns in baseball in 1930, 1932, 1935, 1936, 1939, 1946, 1947, 1948, and 1949. In 1940, the USC basketball team was widely considered to be the best in the nation, and participated in the nascent NCAA tournament, but they lost their bid for the national title when they were upset in the national semifinal at Kansas City, against Kansas, when the son of opposing coach, Phog Allen, made a basket with seconds left for a one-point victory. Despite the loss, the Helms Athletic Foundation later retroactively selected USC as the 1940 national champions.
Barry was also a valued part of the USC football teams which claimed national championships in 1931, 1932, and 1939, as well as seven PCC titles and five Rose Bowl victories. He was Jones' top assistant on the sidelines from 1929 to 1940, also serving as the team's chief scout and coach of the "Spartan" scout team. Barry was often credited by the "Headman" with devising the strategies that proved most effective in shutting down opponents. Although such titles were not used at the time, Barry's position would likely have been equivalent to that of the modern defensive coordinator. The team's football successes included a 25-game winning streak from 1931 to 1933, and the undefeated 1938 team's 7–3 victory in the Rose Bowl over Duke — a team which had previously held every opponent scoreless.