Everything changed on December 8 with the declaration of war by Congress. That day Roosevelt wired Churchill: “Today all of us are in the same boat . . . and it is a ship which will not and cannot be sunk.”¹ Churchill immediately began making travel plans to Washington, even though Roosevelt worried about his future guest’s safety on the Atlantic crossing. Protected by three destroyers and weathering gale-force winds, the Duke of York arrived at Norfolk Navy Yard in Virginia on December 22—with the president meeting the prime minister at a Washington airfield shortly thereafter.

How concerned was Roosevelt that there might be a leak about Churchill’s voyage? First Lady Eleanor Roosevelt remembered being told by her husband “that we would be having some guests visit us” that December. “He told me that I could not know who was coming, nor how many, but I must be prepared to have them stay over Christmas,” she wrote years later in The Atlantic. “He added as an afterthought that I must see to it that we had good champagne and brandy in the house and plenty of whiskey.”²

Once he was safely inside the White House, news of Churchill’s visit prompted banner headlines in newspapers around the world, and radio stations interrupted their broadcasts to announce his arrival. The two comrades in arms lost no time settling down for the first of many long discussions to plan military operations. Thus began the first of the prime minister’s five sojourns on American soil for consultations with FDR about the course of the war and its aftermath. The two leaders spent 113 days together between 1941 and 1945, and Churchill stayed at the White House on four different occasions. He also traveled with Roosevelt to the presidential retreat in Maryland (then called Shangri-La and today Camp David), as well as to Roosevelt’s beloved home in Hyde Park, N.Y.

Having Churchill as a guest in the Rose Bedroom of the White House meant that the president and his staff adapted to Churchillian ways. The Monroe Room on the Second Floor was converted into a map room to display the movement of troops and ships. His personal secretaries set up workspaces in the Lincoln Study. The visitor did much of his work—dictation of correspondence, reports, and speeches—after dinner and into the early morning hours. A self-described “tardy riser,” he liked to lounge in bed reading newspapers and catching up on affairs until lunchtime, and following that meal usually retired to his suite for an afternoon nap. But when the sun went down, he came alive for long conversations with his host or for composing his endless stream of documents.

In her book, On My Own (1958), Eleanor Roosevelt registered some displeasure with Churchill’s long-established routine. “They could talk for hours after dinner on any number of subjects,” she observed. “My husband, however, was so burdened with work that it was a terrible strain on him to sit up late at night with Mr. Churchill after working until 1 or 2 A.M. and then have to be at his desk early the next day while his guest stayed in his room until 11 A.M.”³ Some memoirs detailing Roosevelt’s presidency mention that that he often needed time to recover from Churchill’s visits.

Both figures were outsized political personalities with immense confidence in themselves and what they were doing. Though Churchill was eight years older than Roosevelt, the prime minister understood that the president served as both head of state and head of government—and that Roosevelt had occupied this dual position since early 1933. Recognizing these realities, as well as America’s much larger population and capacity for resources, the prime minister tended to defer to Roosevelt, despite differences of opinion that occurred, particularly in the later years of the war. Interestingly and despite trips abroad to Casablanca, Tehran, and Yalta, Roosevelt never visited Britain as president. Churchill, whose mother was an American, kept crossing the Atlantic for conferences at the White House and elsewhere.

The first visit from late December 1941 through early January 1942 was not only the longest but also the one that aroused the most curiosity and public interest. On December 23, Roosevelt and Churchill held a joint press conference. The next day the pair participated in the annual lighting of the National Christmas tree. On Christmas Day, they attended morning church services—and ended a round of White House events with a 90-minute discussion in Churchill’s suite. On December 26, the prime minister addressed a joint meeting of Congress, the first of three times (between 1941 and 1952) that he spoke to members of both the House of Representatives and Senate.

The evening after his speech at the Capitol, Churchill experienced what he called “a dull pain over my heart.” During an examination the following day, his doctor Sir Charles Wilson, later named Lord Moran, found that the “symptoms were those of coronary insufficiency,” a diagnosis he didn’t share with his patient.⁴ Though Wilson suggested slowing down, Churchill kept to his busy schedule and headed to Ottawa for a speech to the Canadian Parliament on December 30. In his diary, published as Churchill in 1966, Lord Moran uses the phrase “heart attack” to describe the incident.⁵ Medical professionals who have more recently studied Churchill’s records dispute that assessment.

Besides his public activities and a succession of planning meetings with Roosevelt and his war council, Churchill supplied a constant flow of reports and memoranda back to government officials in London. One update he wired to Clement Attlee, the deputy leader of the House of Commons and Lord Privy Seal, on January 3, 1942 is revealing in its description of what it was like to reside and work in the White House. Each page of the prime minister’s account—now available in the National Archives outside London—is marked with a warning in red: “HUSH—MOST SECRET.”

“We live here as a big family in the greatest intimacy and informality, and I have formed the very highest regard and admiration for the President,” Churchill said. “His breadth of view, resolution and his loyalty to the Common Cause are beyond all praise.”⁶ Churchill’s opinion of the congenial domesticity is probably confirmed most dramatically by repeating an anecdote involving the president and his guest. In The Grand Alliance (1950), the third of six volumes comprising Churchill’s historical memoir, The Second World War, he notes that Roosevelt made a middle-of-the-night decision to call the Allies fighting the Axis countries the “United Nations” rather than the “Associated Powers.” In the prime minister’s account, “The President was wheeled in to me on the morning of January 1. I got out of my bath, and agreed to the draft.”⁷

Roosevelt’s recollection of what actually happened is somewhat more colorful. In F.D.R., My Boss (1949), his personal secretary Grace Tully remarked that the president later informed her about the incident, “You know, Grace, I just happened to think of it now. He’s pink and white all over.”⁸

Margaret (Daisy) Suckley, a distant relative and confidante of President Roosevelt, corroborated the story. In her diary, published as Closest Companion (1995), Suckley says the president “called to W.S.C. & in the door leading to the bathroom appeared W.S.C.: a ‘pink cherub’ [FDR said] drying himself with a towel, & without a stitch on!”⁹

Though Churchill denied ever uttering the quip often attributed to him during the encounter—“You see, Mr. President, I have nothing to conceal from you”¹⁰—the prime minister did, indeed, report to King George VI after his return later that January: “Sir, I believe I am the only man in the world who has received the head of a nation without any clothes on.”¹¹

The extended White House stay as the war began nurtured a personal bond between Churchill and Roosevelt. The president, in fact, sent a “Dear Winston” letter in March 1942 that included this advice: “I know you will keep up your optimism and your grand driving force, but I know you will not mind if I tell you that you ought to take a leaf out of my notebook. Once a month I go to Hyde Park for four days, crawl into a hole and pull the hole in after me. I am called on the telephone only if something of really great importance occurs.”¹²

Churchill, however, relished action to the point of being somewhat of a daredevil and made more than two dozen trips abroad for meetings or battlefield visits during the war. But his time in Washington was special and sometimes quite out of the ordinary.

In the memoirs of the prime minister’s chief military assistant, General Hastings Ismay relates what happened in September 1943 during Churchill’s fourth visit to the White House. “The President had to go to Hyde Park before Churchill finished all that he wanted to do,” Ismay notes. “On leaving, he said, in so many words, ‘Winston, please treat the White House as your home. Invite anyone you like to any meals, and do not hesitate to summon any of my advisers with whom you wish to confer at any time you wish.”¹³

Churchill seized the opportunity, later stopping at Hyde Park to report what he’d done. Ismay’s comment on Churchill’s decision to continue to conduct business at 1600 Pennsylvania Avenue without the president in residence is striking: “I wonder if, in all history, there has ever existed between the war leaders of two allied nations, a relationship so intimate as that revealed by this episode.”¹⁴

When Churchill became prime minister for a second time in 1951, he made trips to the United States on three different occasions—in 1952, 1953, and 1954. For the last one, the then-79-year-old leader wrote President Dwight Eisenhower, “My dear Friend,” proposing to “stay four or five days . . . at the [British] Embassy.”¹⁵ Eisenhower, who had served as Supreme Allied Commander in Europe during World War II and worked closely with Churchill, came up with a different plan, which he expressed in an incomplete sentence: “Am desirous that you stay with me . . . at the White House.”¹⁶ From the morning of June 25 until the afternoon of June 29, the prime minister engaged in his usual round of meetings, conversations, and meals with American officials. Despite being increasingly frail, the guest valued his return to 1600 Pennsylvania Avenue, wiring Eisenhower, “We have many pleasant and enduring memories of our visit to the White House.”¹⁷

Five years later (in May 1959), President Eisenhower welcomed Britain’s most prominent statesman—and still an incumbent member of Parliament—back to Washington for yet another White House stay. Ike even took Churchill, a student of the American Civil War, to his farm in Gettysburg via helicopter to show him the nearly century-old battlefield from the air. Describing Churchill’s departure at the end of this stay, John Eisenhower, the president’s son and a noted historian, remarked that the years and several strokes had taken their toll on Britain’s bulldog. But he still commanded respectful attention: “When he left the White House after the visit, the entire presidential staff poured out to the northwest gate to send him off in his limousine, the members viewing him half in affection and half in awe.”¹⁸

That affection and awe only increased during Churchill’s final years. President John F. Kennedy considered Churchill a hero and invited him to return to the White House a few months after the young president’s inauguration in 1961. By that point such a journey was impossible and the offer was politely declined. Yet, two years later at a White House ceremony, Kennedy awarded Churchill honorary American citizenship, the first time a native of another country was so recognized by an Act of Congress. In his remarks, Kennedy, himself a Pulitzer Prize-winning author, praised the honoree’s ways with words: “In the dark days and darker nights when England stood alone . . . he mobilized the English language and sent it into battle.”¹⁹

Even though Churchill could not make the journey to Washington, he composed a statement that his son, Randolph, read. In the eight-volume collection of Churchill’s “complete speeches”—8,917 pages in total—this address is the final one, and it combines both personal and historical reflections. “In this century of storm and tragedy,” he wrote, “I contemplate with high satisfaction the constant factor of the interwoven and upward progress of our peoples. Our comradeship and our brotherhood in war were unexampled. We stood together, and because of that fact the free world now stands.”²⁰

Churchill died on January 24, 1965, and Eisenhower traveled to London for the state funeral. In his tribute, he called his friend a “soldier, statesman, and citizen that two great countries were proud to claim as their own. Among all the things so written or spoken, there will ring out through all the centuries one incontestable refrain: Here was a champion of freedom.”²¹ Freedom’s champion felt right at home in America, and the phrase he coined in 1944 to describe the enduring alliance between the United Kingdom and United States—“a special relationship”—also characterized his own personal association with the White House.

Robert Schmuhl is the Walter H. Annenberg-Edmund P. Joyce Professor of American Studies and Journalism at the University of Notre Dame. He recently served as a Visiting Research Fellow at the Rothermere American Institute at the University of Oxford, where he worked on his forthcoming book, Mr. Churchill in the White House.