His father, Richard Head Welles, was a successful inventor and businessman who made a fortune inventing a carbide bicycle lamp. His mother, Beatrice Ives, was an accomplished pianist and spoken word performer. By the age of six, his parents were separated and Welles moved back to Chicago with Beatrice where she had family. Not long after they arrived in Chicago, however, his beloved mother would die of jaundice when Welles was just nine years old. His father, losing his battle with alcohol, would die when Welles was only 15.
In the wake of Ives’ death, Dudley Crafts Watson (1885-1972), a native of Wisconsin and a cousin of Beatrice Ives, became Welles’ guardian in Chicago. Watson, a vocal advocate for the arts, was the very first director of the Milwaukee Art Institute–which was renamed from the Milwaukee Art Society shortly after Watson’s arrival, and is known today as the Milwaukee Art Museum.