After graduating high school in 1974, Captain Crawford joined the United Stated Army Military Police Corps. In 1977, he went to work for the Federal Bureau of Prisons and then joined the Terre Haute, IN Police Department in 1979. Captain Crawford attended Indiana State University during this time. In 1986, he joined the United States Marshals Service and served in multiple positions throughout his career with a duration as Interim Chief Deputy. Captain Crawford retired from the US Marshals Service as a Senior Inspector after 21 years of service.