After the 1941 attack on Pearl Harbor, more and more jobs are available to men like Malcolm who are too young to enlist in the U.S. Army. Having heard so much about New York, Malcolm gets a job on the wait staff of the Yankee Clipper, a train that runs between Boston and New York. Ella encourages this, given her disappointment over Malcolm’s ongoing relationship with Sophia. Nevertheless, Sophia and Malcolm continue to see each other often.

On his first trip to New York, Malcolm falls in love with Small’s Paradise, a historic Harlem nightclub. Later, he goes to see Dinah Washington and Lionel Hampton perform at the Savoy Ballroom, which dwarfs the Roseland in size and stature.

Malcolm’s insubordination and rudeness to customers cause him to be fired from the Yankee Clipper. He gets a job as a day waiter at Small’s Paradise where he thrives, learning various hustles from the old-timers who frequent the nightclub during the daytime.

Malcolm describes “the numbers,” the dominant betting system in Harlem in the 1940s. Like many young men and women, Malcolm bets his daily tips on guessing the last three numbers of the Stock Exchange’s daily U.S. sales. A winning dollar bet returns $600, and larger bets can win enough money to buy a controlling interest in a neighborhood bar or restaurant.