Character Analysis
Henry is the eldest of the Alden children; though his age is never stated in the first book, we know that he's about 14 years old from later books in the series. From the first chapter, when he chooses bread over cake for the children's dinner, we understand that Henry is practical and responsible. Appropriately, then, once the children settle into the woods, Henry wastes no time in finding a job: "Today I'll go to town and try to get some work to do. I can cut grass or work in a garden or something. Then we'll have something besides milk for breakfast" (5.8). He sees providing for the family as his most important responsibility. Think of him as a mini dad.
The thing is, providing for his siblings isn't Henry's only responsibility. He also feels a strong urge to watch over his younger brother and sisters—like, with his own two eyes instead of his wallet. Sometimes, his urge to protect comes into conflict with his duties as the family breadwinner. When Benny begs for milk, for instance, Henry worries about leaving his family unprotected. He tells Jessie, "I don't want to leave you girls alone" (3.40). Finally realizing he can't be everywhere at once, Henry leaves to get the milk—and, of course, his family is fine without him. Contrary to gender norms of the day, the girls hold down the fort just fine on their own.
Henry's role as the family protector makes him cautious in other ways, too. (Hey, being on the lam can make anyone a little paranoid.) Even around friendly adults like Dr. Moore, Henry carefully chooses his words—when the doctor asks about the children's mother, "Henry did not know what to say" (9.20). He's just trying to be cautious, but he keeps things so close to the vest that it takes a crisis (Violet's illness) for him to open up and ask for, dare we say it, much-needed help.
Still, generally speaking, Henry does a good job taking care of his family. He's a good little father figure, forming a makeshift parental unit with Jessie. When there's a problem, like the possibility of an intruder in the woods, he and Jessie talk it over and deal with it: "The next morning Jessie and Henry talked about the queer noise. They did not tell Violet and Benny" (7.1). Though Henry's masculinity is emphasized through his job and his other attributes—he's a good runner, for instance—we also know that he's a caring big brother who's both generous and thoughtful. Whether it's a cookie or prize money, Henry pockets any reward he receives so he can share it with the rest of the gang. Aw.
Henry James Alden's Timeline