He taught school.
In 1885 he went to Wichita, Kansas, where he studied law in the office of G. W. C. Jones, and in 1888 was admitted to the bar.
In 1885 he was elected county attorney of Ford County, which office he held for two terms. On January 1, 1900, he was appointed judge of the Thirty-first Judicial District and served in that capacity until September 17, 1906, when he resigned to enter the race for Congress. He was elected as the representative of the Seventh Congressional District that year, re-elected in 1908 and again in 1910, but died suddenly from apoplexy while seated at the breakfast table on the morning of September 18, 1911, before completing his third term. While in Congress Mr. Madison was a stanch supporter of President Roosevelt's policies and was a member of the committee to settle the Ballinger-Pinchot controversy.
He was president of the Kansas League of Republican Clubs in 1896-97, was an active member of the Sons of Veterans; was frequently called upon to serve as delegate to conventions, and his services were in great demand as a campaign orator.
Madison was elected as a Republican to the Sixtieth, Sixty-first, and Sixty-second Congresses and served from March 4, 1907, until his death in Dodge City, Kansas,