Boucher graduated from Grantsville (Md.) High School after receiving a Senatorial Scholarship from Garrett County to go to St. John's College in Annapolis. In his freshman year (1925), he went out for football practice, which had already begun. He had never seen a football or lacrosse game before attending St. John's. He lettered in football in 1926, '27, and '28.
Long John played in the first lacrosse game he had ever seen, and played in every minute of every game of his college career. He was a 1929 first team All-American; the first student at St. John's ever to receive such an honor. By his senior year, he had perfected his "Long John Flip" - a move he had learned from teammate Ernie Cornbrooks in which the 210-pound defenseman flipped a dodging attackman over his knee. This obviously was a dramatic and dangerous spectacle, which was soon outlawed by a new holding rule intended to lessen the use of this move. Long John played on St. John's first national championship team in 1929.
After graduation in 1929, Long John accepted a position as freshman coach of football, basketball, and varsity lacrosse at Randolph-Macon College in Virginia for the season of 1929-30. In 1930 he returned to Baltimore to coach football and lacrosse and teach history at Woodbrook School. From 1931-33 he coached swimming and lacrosse and assisted in football at Tome School in Maryland. In 1930, Long John played some games for Penn Athletic Club in Philadelphia and in 1931 played for Mt. Washington Lacrosse Club. The summer of 1931 he played defense for the Cornwall Colts of the Canadian Professional Box Lacrosse League. In 1931 he played for the Baltimore Rough Riders in the newly formed professional league. The league broke up after two months with Baltimore in the lead without a loss. New Year's Day of 1930, he played an exhibition football game for the Virginia All-Stars in Richmond against the New York Giants of the National Professional Football League. Football seasons of 1930 and 1931, Long John played for Irvington Football in a semi-pro league in Baltimore. At the close of the school year of 1933, he left the coaching and teaching career to work for the fountain sales division of Coca-Cola Company.