[1] His paternal grandfather, John C. Calhoun, served as the Vice President of the United States from 1825 to 1832.

[1][2] In 1866, Calhoun entered in a partnership with James R. Powell, a businessman from Montgomery, Alabama, whereby he moved freedmen from the Southeast to Yazoo County, Mississippi, where they worked on new plantations.

[1] By 1869, Calhoun moved to the Florence Plantation in Chicot County, Arkansas, which was inherited by his wife through her mother.

[2] By 1881–1882, he acquired a few more plantations in Chicot County: Harwood, Hebron, Luna, Fawnwood, Patria, Hyner's, and Latrobe.

[2] He teamed up with investors J. Baxter Upham of Boston and Austin Corbin of New York City.