Painting depicts a young boy, wearing a red sports jersey, jeans, white socks and black sneakers holding a tennis ball in his left hand and a racquet over his right shoulder walking off of a tennis court. In the back ground is a blue sky and a chain link fence with a wind screen and a "ghost" image of Arthur Ashe reaching out with a racquet.
According to the National Art Museum of Sport's catalogue, the artist's statement about this artwork is as follows: "Richard Wilson strives for his pastel paintings to tell stories of the subjects' optimism or introspection. In His Shadow does this by portraying a young tennis player walking off the court inspired by his idol, the great tennis player and humanitarian Arthur Ashe. Wilson sketches with hard pastel and fills in with layers of soft pastel."