A member of the Boston Brahmin Crowninshield family, Bradlee was born in Boston, Massachusetts, and attended Dexter School before finishing at St. Mark's School. His father was Frederick Josiah Bradlee Jr., a direct descendant of John Bradley — the first of the Bradleys to come to America — who in 1630 helped build what is now Dorchester, Massachusetts. His mother, Josephine de Gersdorff, was awarded the Legion of Honor for helping keep children safe from Nazi Germany and France during World War II. Bradlee's maternal grandfather, Carl August de Gersdorff (1865—1944), was a wealthy New York lawyer and his maternal grandmother was Helen Suzette Crowninshield (1868—1941), a painter, author and scion of the noted Crowninshield family. His great-great-uncle was Joseph Hodges Choate, who was an American lawyer and the American ambassador to Great Britain from 1899—1905; and his great uncle was Francis (Frank) Welch Crowninshield, the creator and editor of Vanity Fair, and a roommate of Conde Nast.

Bradlee received his naval commission two hours after graduating in 1942, joined the Office of Naval Intelligence and worked as a communications officer in the Pacific Theatre during World War II. His duties included handling classified and coded cables. The main ship on which Bradlee served was a destroyer, the USS Philip. He fought off the shores of Guam and arrived at Guadalcanal with the Second Fleet; his main battles were Vella Lavella, Saipan, Tinian, and Bougainville. He also fought in the biggest naval battle ever fought, the Battle of Leyte Gulf in the Philippines. He made every landing in the Solomon Islands campaign and Philippines campaign.

When Bradlee married for the first time, it was to Jean Saltonstall. They had one son, Ben Bradlee Jr., who was raised in Cambridge by his mother and her second husband, Bill Haussermann. Bradlee Sr. is estranged from Ben Bradlee Jr., former deputy managing editor at the Boston Globe.

After the war, in 1946, Bradlee Sr. became a reporter at the New Hampshire Sunday News, a venture he helped launch. In 1948 he started working for The Washington Post as a reporter. He got to know associate publisher Philip Graham, who was the son-in-law of the publisher, Eugene Meyer. On Nov. 1, 1950, Bradlee was alighting from a streetcar in front of the White House just as two Puerto Rican nationalists attempted to shoot their way into Blair House in an attempt to kill President Harry S. Truman. In 1951 Graham helped Bradlee become assistant press attaché in the American embassy in Paris, France.

In 1952 Bradlee joined the staff of the Office of U.S. Information and Educational Exchange (USIE), the embassy's propaganda unit. USIE produced films, magazines, research, speeches, and news items for use by the CIA throughout Europe. USIE (later known as USIA) also controlled the Voice of America, a means of disseminating pro-American "cultural information" worldwide. While at the USIE, according to a Justice Department memo from an assistant U.S. attorney in the Rosenberg Trial, Bradlee was helping the CIA manage European propaganda regarding the spying conviction and execution of Julius and Ethel Rosenberg on June 19, 1953.

Bradlee was officially employed by USIE until 1953, when he began working for Newsweek. While based in France, Bradlee divorced his first wife and married Antoinette Pinchot. At the time of the marriage, Antoinette's sister, Mary Pinchot Meyer, was married to Cord Meyer, a key figure in Operation Mockingbird, a CIA program to influence the media.

Antoinette Bradlee was also a close friend of Cicely d'Autremont, who was married to James Jesus Angleton. Bradlee worked closely with Angleton in Paris. At the time, Angleton was liaison for all Allied intelligence in Europe. His deputy was Richard Ober, a fellow student with Bradlee at Harvard University.

In 1957, while working as a reporter for Newsweek, Bradlee created controversy when he interviewed members of the FLN. They were Algerian guerrillas who were in rebellion against the French government at the time. According to Deborah Davis, author of Katharine the Great about Katharine Graham, this had all the "earmarks of an intelligence operation." As a result of these interviews, Bradlee was given an expulsion order from France; however, the order was suspended and finally repealed.

As a reporter in the 1950s, Bradlee became close friends with then-Senator John F. Kennedy, who lived nearby. In 1960 he toured with both Kennedy and Richard Nixon in their presidential campaigns. He later wrote a book, Conversations With Kennedy (W.W. Norton, 1975), recounting their relationship during those years. Bradlee was, at this point, Washington Bureau chief for Newsweek, a position from which he helped negotiate the sale of the magazine to the Washington Post holding company. Bradlee maintained that position until being promoted to managing editor at the Post in 1965. He became executive editor in 1968 and, in 1978, married fellow journalist Sally Quinn. Quinn and Bradlee have one child, Quinn Bradlee, who was born in 1982 when she was 41 and Bradlee was 61. In 2009, they appeared with Quinn Bradlee on the Charlie Rose show on PBS and spoke of their son's having been born with Velo-cardio-facial syndrome, also known as 22q11.2 deletion and Shprintzen syndrome (named after Dr. Robert Shprintzen who first identified the disorder in 1978 and also diagnosed Quinn Bradlee).

Bradlee retired as the executive editor of the "Post" in September 1991, but continues to serve as its Vice President At Large.

Under Bradlee's leadership, The Washington Post took on major challenges during the Nixon Administration. In 1971 The New York Times and the Post successfully challenged the government over the right to publish the Pentagon Papers. One year later, Bradlee backed reporters Bob Woodward and Carl Bernstein as they probed the break-in at the Democratic National Committee Headquarters in the Watergate Hotel. Ensuing investigations of suspected cover-ups led inexorably to Congressional committees, conflicting testimonies, and ultimately, to the resignation of Richard Nixon in 1974. For decades, Bradlee was one of only four publicly known people who knew the true identity of press informant Deep Throat, the other three being Woodward, Bernstein, and Deep Throat himself.

In 1981, Post reporter Janet Cooke won a Pulitzer Prize for "Jimmy's World", a profile of an eight-year-old heroin addict. Cooke's article turned out to be based on a fiction: there was no such addict. As executive editor, Bradlee was roundly criticized in many circles for failing to ensure the article's accuracy. After questions about the story's veracity arose, Bradlee (along with publisher Donald Graham) ordered a "full disclosure" investigation to ascertain the truth. At one point during the investigation, Bradlee angrily compared Cooke with Richard Nixon over her attempted coverup of the fake story. Bradlee personally apologized to Mayor Marion Barry and the chief of police of Washington, D.C., for the Post's fictitious article. Cooke, meanwhile, was forced to resign and relinquish the Pulitzer.

Bradlee published an autobiography in 1995, A Good Life: Newspapering and Other Adventures. He had an acting role in Born Yesterday, the 1993 remake of the 1950 romantic comedy.

On May 3, 2006, Bradlee received a Doctor of Humane Letters from Georgetown University in Washington, D.C.. Prior to receiving the honorary degree, he taught occasional journalism courses at Georgetown.

In 1991 he was persuaded by then-Governor of Maryland William Donald Schaefer to accept chairmanship of the Historic St. Mary's City Commission and continued in that position through 2003. He also served for 12 years as a member of the board of trustees at St. Mary's College of Maryland, and endowed the Benjamin C. Bradlee Annual Lecture in Journalism there. He continues to serve as vice chairman of the school's board of trustees.

In the fall of 2005, Jim Lehrer conducted six hours of interviews with Bradlee on a variety of topics...from the responsibilities of the press to the differences between Watergate and the Valerie Plame case. The interviews were edited for an hour-long documentary called Jim Lehrer and Ben Bradlee, which premiered on PBS on June 19, 2006.

Bradlee serves on The Washington Post's editorial board as vice president at large. Bradlee lives at his home, the Todd Lincoln House in Georgetown, Washington, DC, The middle part of the house was built in 1792.

Actor Jason Robards portrayed Bradlee in the film All the President's Men, winning a Best Supporting Actor Oscar for his performance. G.D. Spradlin played the role of Bradlee in Dick, a spoof of Watergate. Henderson Forsythe played Bradlee in the romantic comedy Chances Are.