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After living in the Home, ten-year-old Bud Caldwell is placed with the Amos family. This marks his sixth foster home since his mother's death when he was six years old. Bud carries with him his cherished suitcase containing his special belongings and his mother's mysterious items.

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Bud has a terrible experience at the Amos house when Todd Amos, their son, plays a cruel prank on him. After being locked in a shed full of hornets and getting stung multiple times, Bud fights back against Todd. This leads to his decision to run away.

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After a night of wandering, Bud goes to the mission for breakfast. Here, he experiences the harsh reality of the Great Depression as he sees many other hungry people in line for food. He also receives valuable information about finding work.

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Bud visits the library where Miss Hill, a kind librarian who knew his mother works. He finds out that she is married and moved to Chicago, the new librarian shows him a atlas and how long it would take to get there.

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While planning his escape, Bud meets Bugs, another orphan boy, under a tree. They make plans to hop a train to Chicago, where Bugs hopes to find work. This shows Bud's first attempt at friendship and independence.

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Bugs and Bud visit their first Hooverville and meet all kinds of different people. Here they get the information they need for their plans to hop a train. Bud also gets his first kiss.

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Bud misses the train that Bugs successfully jumps onto, leading to a significant turning point. This failure forces him to change his plans and sets him on a different path toward finding Herman E. Calloway.