This honors project was born out of a desire to understand individuals who abandoned political glory in favor of serving other leaders. I wanted to study and know who can go head-to-head with \u2014 and command the respect of \u2014 the U.S. President on a daily basis. I limited my search to friends of the presidents who held powerful positions: I identified Harry Hopkins, Robert McNamara, and Condoleezza Rice. This thesis is broken into the following sections. To begin, we follow each official in their rise to prominence and discover how they captured the attention of their respective presidents. Next, we delve into their relationships with the Oval Office -- what is similar or different about each of their connections with the presidents. The bulk of the work focuses on pivotal moments in our country's history \u2014 events that shaped the United States of today. Specifically, we look at the New Deal, World War II, the Cuban Missile Crisis, the Vietnam War, the Middle East, and nuclear weapons proliferation. Then, we dissect similarities and differences between their relationships with their presidents, and wrap up with some takeaways about how one could go about becoming a presidential advisor. Their distinctive styles can be grouped into doers or planners. Hopkins and McNamara were proud and self-proclaimed doers. Rice stands alone as a fantastic planner. If one seeks to emulate any of these three, there are three things to commit to. First, skills both matter and don't matter. Second, there are two paths to getting presidential attention and becoming close enough for them to seek one out for advice. The first is to understand which wheels need greasing, and grease them. The other is to have a potential solution to an unsolved problem -- that is powerful. Be great, a maverick, and public, or look to create your own role from scratch and hope that you are an expert when a time of great need comes. Third, once you are friends with and have the political ear of the president, know that loyalty is the only thing that truly matters. This thesis is an attempt to better understand leadership through the lens of powerful followers. This project strives to inform the reader of the context within which these actors played, the actions that they took, and the consequences that were incurred, all while being personally close to the most powerful position on the planet. I have tried to give context and understanding for pivotal moments in American history while shining a spotlight on a few underappreciated historical actors.