In 1900 he was working as a prominent lawyer in Lexington Kentucky when he was beaten for helping register black voters by a white man who opposed his efforts.

He attended compulsory schools until the age of eleven when he was sent to England for private tutoring, and then enrolled in Trinity College, Oxford University where he studied for three years.

He left Oxford without receiving a degree and made a two year tour of the East Indies including Sumatra and Java.

Ten days later he took a six month cruise to South America and the Caribbean as a cabin boy on the Lepanto captained by Cyrus E. Staples.

He then moved to Decatur, Alabama where he became principal of a public school, and then to Brinkley, Arkansas and finally Memphis, Tennessee.

[2] He returned to journalism, and owned and edited a number of papers throughout the country, including the Colored Citizen in Pittsburgh, Pennsylvania, the Chronicle in Evansville, Indiana, and the Negro American in Birmingham, Alabama, where he settled for some time.

[1] In Birmingham 1887, together with A. L. Scott, Samuel Roebuck, George Turner, J. H. Thompson, Sandy Goodloe, D. A. Williams, A. T. Walker, William R. Pettiford, and J. T. Jones he incorporated the Robert Brown Elliot School of Technology in Birmingham, the first school of its kind for blacks in the U.S.[3] He also was a pamphlet writer, writing pamphlets on African-American history and issues.

[8] Benjamin is claimed to have been admitted to the bar in 12 states,[9] including Virginia, Tennessee, California, Rhode Island, and Alabama.

[4] In 1895, while practicing law in Rhode Island, Benjamin, who was ordained in the African Methodist Episcopal Church, was nominated to the position of chaplain of the United States House of Representatives.

[6] That day he chastised a white man, Michael Moynahan, for harassing a group of black men registering to vote.