University of Mississippi.
Massingale moved to Fort Worth, Texas in 1887 and was employed for a short time as a section hand while he continued to study law. He was admitted to the bar in 1895 and commenced practice in Cordell, Oklahoma, in 1900. During the Spanish–American War, Massingale served as a private in Company Doctorate, Second Texas Infantry.
He ran unsuccessfully for the Sixtieth Congress in 1906.
Massingale was elected as a Democrat to the Seventy-fourth and to the three succeeding Congresses and served from January 3, 1935, until his death on January 17, 1941. Massingale died in Washington, District of Columbia, January 17, 1941 (age 70 years, 168 days).
He is interred in Lawnview Cemetery, Cordell, Oklahoma.
He served as a member of the Oklahoma Territorial Council in 1902.