Chapter 3 details the intense and dynamic experience of Dick Goodwin during the 1960 presidential campaign, as he joined Senator John F. Kennedy’s team on his private plane, the “Caroline.” Named after Kennedy’s daughter, the aircraft served as a mobile campaign headquarters, equipped with all necessary amenities for a grueling schedule.

From September to November 8, 1960, Dick, part of the small traveling team, navigated the high-energy, relentless pace of the campaign trail. The “Caroline” was more than a plane; it was a luxurious flying office where speeches were crafted, strategies were discussed, and campaign logistics were managed. Alongside other key figures like Ted Sorensen and Dave Powers, Dick worked tirelessly, often sacrificing food and sleep, fully immersed in the campaign.

The campaign officially began on September 7 in Detroit, and the team quickly moved to various states, including Idaho and Oregon. Despite the exhaustion, moments of camaraderie and levity, such as playing historical recall games about presidential slogans, kept the team’s spirits high. Kennedy himself, with his charismatic presence, often participated in these games, using them as inspiration for his speeches.

A pivotal moment in the campaign occurred on September 9 at the Shrine Auditorium in Los Angeles, where Kennedy delivered a major speech on civil rights.