The One with the Long Shadow" is a novel that revolves around the life of Jane Bister, a five-year-old girl living in London. She comes from afamily  that strongly advocates for women's rights, with her grandmother being a prominent fighter for gender equality and women's suffrage.

 Judy's parents passed away when she was a baby, and she was taken into the John Grier Orphanage in New York City. It is at the orphanage that Judy discovers her talent for writing, which eventually catches the attention of a trustee known as "John Smith." This trustee offers her a scholarship to attend Lincoln Memorial High School, but Judy has no idea who he really is and affectionately refers to him as "Daddy Long Legs." Despite not knowing his true identity, Judy considers him her only family and becomes deeply attached to him.

Throughout her time at Lincoln Memorial, Judy forms close friendships with her roommates, Sallie McBride and Julia Pendleton. Sallie, a shy but sweet girl, develops a strong bond with Judy, while Julia often teases her due to her short and chubby stature. Despite facing insecurities as an orphan, Judy finds solace in her friendships and her passion for storytelling.

Another important character in the story is Joanna Sloane, the manager of the dormitory where Judy resides. Joanna often puts up a facade of cruelty and anger to hide her true emotions. She despises being referred to as "Mrs." as she is still unmarried, but secretly desires to find love and get married.