Bradlee moved to Georgetown in 1957 and one year later a junior senator from the state of Massachusetts moved into the same block. In 1959, Bradlee stood in the backyard garden of John F. Kennedy as he positioned himself for a run for president the next year. Bradlee emerged as the primary method all Newsweek reporters used to get comments and coverage of the emerging political powerhouse. Bradlee traveled often with the candidate, flying to Charleston, W.Va. the day of Kennedy's critical triumph in the overwhelmingly Protestant state.

The night after he won the White House, Kennedy invited Bradlee and his wife over to their house in Massachusetts to celebrate at a quiet dinner.

Some four years later, Bradlee would pen an article entitled "That Special Grace" for the rushed special edition of Newsweek magazine to cover the assassination of President Kennedy. Bradlee would end his piece: "John F. Kennedy is dead, and for that we are a lesser people in a lesser land."