This paper attempts to analyze the challenges facing the organization of the modern White House staff and their domestic and foreign policymaking processes. It acknowledges that while the president does exercise influence over his or her staff through personal management style, it find that it has also developed institutional traits since the establishment of the Executive Office of the President (EOP). These traits include the increasing trend towards internal and external forms of centralization in the White House staff over policymaking authority and direction. The effects from these traits often exacerbate inherent bureaucratic infighting and hamper substantive policymaking. Furthermore, the rise of political partisanship, along with changes in the media landscape due to technological advances, has shifted the political and policymaking environment in the 21st century. By assessing this environmental shift, this paper finds that it is now more difficult for presidents and their White House staffs to think critically and expansively about domestic and foreign policy issues. This paper argues that given these developments, it is more necessary than ever for White House staffs to be organized in a way that promotes a wide range of policy advice and options for the president and an honest broker to coordinate them. This paper argues that such an organization can be achieved through the application of Alexander George’s theory of multiple advocacy. It assesses George’s theory and the history of its application within both the operations of the White House policy councils and the functions of key aides, the White House Chief of Staff (COS) and the Assistant to the President for National Security Affairs (APNSA). Through this assessment, it concludes that a White House staff organized around the principles of multiple advocacy and honest brokerage is not only the best way to foster substantive domestic and foreign policymaking, but also that the principles can still be applied successfully in the 21st century environment.