During Cleveland's second term, Taylor was the first African American ever nominated for a diplomatic appointment to a predominantly white country, Bolivia, although he was not confirmed by the Senate.

After leaving Washington, Taylor edited an Atlanta newspaper, The Southern Appeal, and served as dean of the Law Department at Morris Brown College.

Taylor was born into slavery on a plantation near Marion, Alabama, possibly in 1856, although sources differ on the exact year of his birth, as well as other details of his life.

After the Civil War, he moved with his family to Savannah, Georgia, where he was educated at Beach Institute, a school operated by the American Missionary Association.

He stayed in Liberia for only five months, claiming he had returned to campaign for Cleveland’s re-election, although he later made statements strongly critical of Liberian politics and the emigration schemes of the American Colonization Society.

In the run-up to the 1888 presidential election, Taylor participated in founding the National Negro Democratic League at a meeting in Saint Louis, together with Herbert A. Clark and J. Milton Turner.

According to Bruce Mouser, the primary purpose of the League was to prepare lists of African American candidates for “high-level patronage positions” in the event of a Democratic administration.

[11] As the 1892 presidential election approached, Taylor spoke frequently in Kansas, Missouri, Iowa, and neighboring states against prohibition, the so-called “McKinley tariff,” and in support of Democratic candidates.