[2] Because the chief and the council represented different parties, Smallwood was able to accomplish little politically during his years in office.

[2] Politically, Smallwood was very concerned about maintaining the independence of Choctaw Nation and resisting interference from the U.S.

[3] In 1888, the U.S. Government made a payment to Choctaw Nation, and Smallwood called a special session of the council, which authorized that the funds were to be dispersed without an audit by the Net Proceeds Commission.

[2] The payment was for the Leased District, which was originally owned by the Choctaw but had been granted to the United States by treaty in 1855.

[7] During his time in office, Smallwood had advocated for the expansion of Choctaw schools, but due to the divisive political situation, he made little progress.

[2] During the United States Civil War, Smallwood was Captain of the 2nd Choctaw Regiment in the Confederate Army.

[2] Smallwood owned a farm near Lehigh, raised cattle, and ran a dry goods store in town.