Linwood Stepp (1892-1990) was one of at least six children born in the Free Union district of Albemarle County to Lindsay Stepp, a blacksmith, and Jemima Stepp, a homemaker.

He may have commissioned this portrait as a gift to his family. Less than a year after having it made, he moved to Buffalo, New York, and found work in a steel mill.

During World War I, he served in France with the U.S. Army's 349th Field Artillery, rising to the rank of sergeant. He returned to Albemarle County in 1921 to marry Maggie Hansberry, with whom he had three daughters.

The family made its home in Buffalo. After Maggie's early death, Stepp married Gertrude Frazier of Cincinnati, Ohio. Stepp continued to work in Buffalo steel mills until he retired.