He left Kentucky in 1891, moving to Texas and attending Grayson College in Whitewright.

In 1903 he moved to Chickasha, Indian Territory (now Grady County, Oklahoma).

He was later elected the principal of a Chickasha grade school and taught 12 years in .

[1] He held the office until he defeated Evan Dhu Cameron in the 1910 Democratic primary for Oklahoma Superintendent of Public Instruction and won the general election.

[1] Wilson ran in the 1922 Oklahoma gubernatorial election with the endorsement of the Ku Klux Klan, but lost the primary to Jack C.