This thesis explores the roles of art and technology in Don DeLillo’s novels Cosmopolis and Zero K. DeLillo’s works combine art and technology through their depictions of protagonists whom I characterize as rogue capitalists. In Cosmopolis, Eric Packer is a rogue capitalist who yearns to escape the world of financial speculation after seeing a horrific event, while in Zero K, the rogue capitalist figure, Ross Lockhart, wishes to leave the contemporary era by freezing his body. Both characters become “rogues” because they seek to escape the capitalist environment that has made them, and because they negotiate escape, in part, through the use of art. With this project, I hope to answer two questions: (1) Why does DeLillo use the rogue capitalist to bridge art and technology in the novels? (2) Using humanist and posthumanist theory, what is uncovered about how the rogue capitalist functions amid art and technology?