Content Warning: This section features descriptions of child neglect.

Timothy is the eldest and boldest Willoughby sibling. He is 12 years old but tries to act as the parent to his younger siblings in the absence of their actual parents’ attention. Timothy has a “heart of gold, as many old-fashioned boys do, but [hides] it behind a bossy exterior” (2). He creates a point system for his siblings, giving and taking away points based on their behavior. For the most part, Timothy’s rules are unreasonable, and Jane, in particular, grows to resent him. The Willoughby children’s lack of structure and Timothy’s desperate attempts to control the chaos illustrate The Importance of Logical Rules in children’s lives. The nanny helps with this, allowing Timothy to enjoy being a child again without the heavy responsibility of looking after his siblings. Timothy is also creative and full of ideas; for example, he figures out a way to camouflage everyone when the buyers come to the house, and he is also the one who decides how to send Mr. and Mrs. Willoughby away to their deaths. When Timothy grows up, he becomes an attorney and marries Ruth.