In 1942, Malcolm secures a job with a railway company as a dishwasher for their Boston to Washington, DC route. He soon gets promoted and starts selling food on the "Yankee Clipper," a train that travels between Boston and New York City. During his inaugural trip to Harlem, New York, he visits numerous nightclubs, encountering renowned Black celebrities like Dizzy Gillespie and Ella Fitzgerald. Feeling an instant connection, he decides he belongs in this world and becomes a regular at Harlem's most popular venues.

Malcolm is terminated from his railroad job after the company receives complaints about his discourteous behavior. Confident that he can easily find another job due to the thriving wartime economy in America, Malcolm visits his family in Lansing. His striking fire-red hair and zoot suits create quite a stir in Michigan.

Returning to New York, Malcolm takes on a job as a day waiter at Small's Paradise. He learns about Harlem's rich history as a sanctuary for various immigrant groups, including Dutch, German, and Irish. Additionally, he uncovers the reasons behind Harlem's infamy—such as number running, pimping, drug dealing, and theft.