This dissertation examines the political and business career of H. R. “Bob” Haldeman. Scholars studying Richard M. Nixon’s presidency and administration have given very little attention to Haldeman’s career before and after his time as chief of staff. This dissertation argues that in order to understand Haldeman’s actions as chief of staff one needs to have a firm understanding of his career before he entered Nixon’s White House. In contrast to what many have argued, an overt interest in politics and overriding ambition to serve Nixon did not solely drive Haldeman. Instead, the development of Haldeman’s career is best understood through his consistent search for opportunities and activities in which he could alter, reform, or improve existing processes and organizations. Only a study of his entire career brings this motivation to the forefront. Using Haldeman’s recollections, his White House diaries, archival records relating to his business and political career, assessments of the Nixon presidency, and the recently published memoir of his wife, this dissertation provides an in-depth study of his career as a manager in business and politics. This study answers important questions regarding Haldeman’s background, intellectual makeup, and the trajectory of his career by reexamining Haldeman’s work for Nixon and his career in the advertising industry and analyzing how each of these experiences informed his life, skillset, and his managerial behavior. Providing the scholarship with a more complete picture of Haldeman’s life and career augments the understanding of Richard Nixon’s political career and presidency, by filling a critical void with a more comprehensive overview of a close aide and a major figure at the center of the Watergate scandal. An examination of Haldeman’s entire career, moreover, illuminates how significant developments in twentieth century United States political and business history impacted one individual.