When Smith and his wife escaped on the Underground Railroad to Massachusetts, he wrote a letter to his daughter.

He remained in jail for twelve weeks and was sold in 1848 to a New Orleans man named Pipkin.

When a steamer blew up at the wharf in 1849, many were killed and Holmes had an arm dislocated and suffered head injuries.

[2] About that time, Mr. Pipkin committed suicide and when his daughter married, Holmes was sold to Royal Parrish.

He still owed $100 Confederate to the lawyer that drew the papers when the war ended and his freedom was assured.

He was an organizer and served as the first president of the Colored Home of Richmond formed to care for needy African Americans in the city.

[4] That year he was also elected an officer of the Educational and Historical Association of Virginia, an African American literary lyceum led by John W.

[5] Among his congregation was the first black woman to own a bank, Maggie L. Walker, who Holmes baptized in 1878.

[8] In 1896, Holmes appealed on the behalf of the widow of Solomon Marable for the return of his body after his execution and partial dissection by students at the Medical College of Virginia.

The case was subject to an exposé by Richmond Planet publisher John Mitchell, Jr.[10] In 1896, his third wife, Maria Holmes, died.