Small was born in Kankakee County, Illinois, and attended public education at Northern Indiana Normal School, now Valparaiso University,[1] through his senior year.

After schooling, he became a teacher and invested in real estate, eventually owning a farm, a bank, and Kankakee's daily newspaper.

He served as the assistant U.S. Treasurer in charge of the sub treasury at Chicago from 1908 to 1912, and was a delegate to Republican National Convention from Illinois in 1908, 1912, and 1932.

[7] As governor, Small pardoned 20 members of the Communist Labor Party of America, convicted under the Illinois Sedition Act.

[9] Small's reputation for corruption finally caught up with him at the ballot box when he was defeated in the 1928 Republican "Pineapple Primary" by a margin of 63% to 37% against Louis Lincoln Emmerson, the incumbent Illinois Secretary of State.