In 1889, Crawford graduated from the United States Military Academy, where he was a classmate of future army general Charles Dudley Rhodes.

[2] Crawford served as a second lieutenant in the 10th Infantry on the United States frontier between 1889 and 1895, which included military police duty in Oklahoma City until 1890 and assisting the U.S. Commission in dealings with American Indian tribes; between 1891 and 1892 he organized an Apache Indian Company in the 10th Infantry.

Between 1903 and 1907 he taught at Fort Leavenworth, Kansas, in the Infantry and Cavalry School and the Army Staff College.

From 1913 to 1916 Crawford served on the General Staff of the U.S. Army, after which he was in Panama Canal Zone until 1917.

During World War I, Crawford served with the American Expeditionary Force as a brigadier general of the National Army.