Career
He served as the head football coach at Texas Christian University (1915), Millsaps College (1921), Southern Methodist University (1922–1923, with Ray Morrison), and Texas Technical University (1925–1928), compiling a career college football record of 41–23–8. Freeland was also the head basketball coach at Texas Christian University for one season in 1915-1916 and at Millsaps for one season in 1921-1922. In addition, he was the head baseball coach at Texas Christian University (1916), SMU (1923–1924), and Texas Technical (1926–1927), amassing a career college baseball record of 50–47–3.
Freeland was born on January 1, 1887 in Turnersville, Texas and died on August 15, 1953 in Brownwood, Texas.
He played football and baseball at Vanderbilt University, from which he graduated in 1912. He was nominated though not selected for an Associated Press All-Time Southeast 1869-1919 era team
In 1915, Freeland coached football at Texas Christian University, compiling a 4–5 record. In 1922 and 1923, Freeland co-coached the SMU Mustangs football team with his former teammate at Vanderbilt, Ray Morrison.
The two effectively shared the heading coaching duties, with Morrison focusing on the backfield and ends, and Freeland mentoring the linemen.
In 1925, Freeland became the first coach of the Texas Technical Red Raiders football team, then known then as the Matadors. He coached football at Texas Technical from 1925 to 1928, where he had a 21–10–6 record. Freeland was also the first head coach of the Texas Technical Red Raiders baseball team and Texas Technical"s first athletic director
He is credited with designing Texas Technical"s Double T logo and had it put on the sweaters of football players.