In one of the earliest letters to his son during that trip, Charles Chesnutt wrote on February 5, 1906: "Have as good a time as you like, within the limits of strict economy, remembering that I am not carrying you, but merely boosting you along." Edwin, a recent Harvard graduate, was having difficulty finding employment.
"We missed you very much for a day or two," Chesnutt's letter continues, "but are getting a little bit adjusted to your absence. The whole family has become wonderfully fond of you since you left... Much love and best wishes."
Less than 20 years later, in 1923, Chesnutt heard that his son's alma mater was trying to exclude blacks from its dormitories and dining halls. A local newspaper in Cleveland reported flippantly about the discrimination. Chesnutt responded to the editor in an angry letter that he expected more from a Cleveland man, "educated in the public schools where he went to school with colored children." The letter, which elicited an apology from the editor, continued:
Colored students have always lived in the dormitories and eaten in the dining halls at Harvard; I have paid the bills of one of them and ought to know. The "living together" and "eating with white folks" involves no more intimacy than life in a hotel, and you know or ought to know that colored men are received as guests at some of the best hotels in Cleveland.