Taylor was born into a prominent family of plantation owners who moved westward from Virginia to Louisville, Kentucky in his youth. He was commissioned as an officer in the U.S. Army in 1808 and made a name for himself as a captain in the War of 1812. He climbed the ranks establishing military forts along the Mississippi River and entered the Black Hawk War as a colonel in 1832. He also bought a plantation in Louisville, as well as the Cypress Grove Plantation in Jefferson County, Mississippi Territory. These acquisitions included slaves, rising in number to more than 200.