John F. Kennedy embarked on his White House responsibilities in January 1961 with a "youth-can-do-anything" outlook. He quickly discovered that confidence was not enough to ensure success, given the disastrous American invasion of Castro's Cuba and setbacks in Congress over his domestic agenda. Nevertheless, by the end of his first year, he had begun to establish his credibility as a world leader. Moreover, Kennedy's leadership style had matured as he acquired insights into the realities of the nation's highest office. It was that growth that prompted Time to name him 1961's Man of the Year and to commission this cover portrait from Italian painter Pietro Annigoni.
When Annigoni went to the White House to sketch Kennedy, he was struck by the president's pensive, often somber, demeanor, and it was this side of Kennedy that the artist decided to capture. Many readers of Time detested the final portrait, however, including the president himself.