Sir Simon is the ancient ghost that is haunting his ancestral home, Canterville Chase. For more than 300 years he has been successfully terrifying the occupants. Now, with the Americans moving in, he is at a loss as to how to frighten them. He died in the late 1500's when his wife's brothers starved him to death. They did this to him because he supposedly killed his wife (their sister) because she was a bad housekeeper and was plain. Before he crosses over, he gives Virginia a box of jewels.