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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.[1]
During the Spanish–American War, Massingale served as a private in Company D, Second Texas Infantry. He served as a member of the Oklahoma Territorial Council in 1902. The following year he married Anna Canaday, and they had four children. He ran unsuccessfully for the Sixtieth Congress in 1906.[2]
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.[3]