Education
Webster was raised in Fairfield County, Connecticut, and attended Shelton High School and preparatory school at the Hotchkiss School in Lakeville, Connecticut.
Webster was raised in Fairfield County, Connecticut, and attended Shelton High School and preparatory school at the Hotchkiss School in Lakeville, Connecticut.
He played college football at Yale University and was a consensus first-team All-American at the guard position in 1927. Webster next enrolled at Yale University. He played for the Yale Bulldogs football team from 1925 to 1927 at the guard and tackle positions.
During the 1925 season, he was injured and saw only limited action as a substitute at the tackle position.
In September 1926, he again suffered an injury that limited his time with the team He returned to the team in mid-October 1926 and played at the right tackle position.
Despite a further injury in November 1927, Webster became a consensus first-team selection at the guard position on the 1927 College Football All-America Team. In 1928, he became an assistant coach to the Yale football team
After graduating from Yale, Webster was employed by the firm of Guggenheim Brothers in New New York
As a senior at the Hotchkiss School during the 1923-1924 school year, he was captain of the football team and a member of the Olympian gym team, dramatic association, class hockey team, debating union, Saint Luke"s board, track team and baseball team