In The Great Gatsby Jay was very wealthy and successful, he was a Yachtsman Soldier Entrepreneur Bootlegger. He grew up dirt poor and at about 27 he returned home to New York, and took advantage of Prohibition by making millions from bootlegging, and built connections with various gangsters such as Meyer Wolfsheim, who Gatsby claims is "the man who fixed the World 's Series back in 1919". In The Black Boy, Richard grew up poor too. Richards’ dad leaves him and his family at a young age, and his mother because the only Income in the house while they live in poverty and hunger. As he grew older he left Memphis, Tennessee to go to Chicago. Working many unskilled jobs, he was given an opportunity to write. He joined the John Reed Club in Chicago,