Brickley's first coaching job was during his senior year at Harvard, where he served as an assistant to the
University of Virginia football team during the team's August practices. After graduating, Brickley was sought by many schools looking for head coaches, including
New York University and
Penn State. After initially refusing to coach, Brickley eventually accepted the head coaching job at
Johns Hopkins University. In 1916, he led Boston College to its first victory over rival
Holy Cross since 1889. He left Boston College in 1918 to join the
United States Navy Reserve. He was quartermaster for the
Naval Transport Service at the
Hoboken Port of Embarkation and both played and coached for the Naval Transport Service's football team. In January 1919, Brickley was named as the 1918 Collier's All-Service Team first squad fullback by
Walter Camp. Brickley was named head coach at
Fordham University in 1919, however the school later decided to cancel the season. He was an advisory coach for Fordham during the 1921 season when his younger brother, Arthur, was a member of the team. In 1922, Brickley was offered the position of head coach at
Northwestern, but the two sides could not agree on terms and the school hired
Glenn Thistlethwaite instead. ==Owner==