This article examines relationships between men and the role of patriarchal capitalism in F. Scott Fitzgerald's novel The Great Gatsby. It discusses how the novel references two cultural myths about how boys become men - the Horatio Alger story of a boy being mentored by a wealthy older man, and the story of Trimalchio from Satyricon, which highlights connections between ancient traditions of slavery and homosexuality and modern economic practices. The article argues Fitzgerald drew on these references to critique how mentoring relationships in society construct sexuality and how men gain access to wealth and status through political and business connections rather than friendship or love.