On the morning the president and his party made their way up the gangplank to the deck of the USS Quincy, the weather was brisk. A strong wind from the northwest prevented the heavy cruiser from reaching full speed for about fifty minutes. As the ship made its way past Hampton Roads and out beyond the mouth of Chesapeake Bay to the open Atlantic, three escort destroyers formed an anti-submarine screen ahead of the Quincy, while the light cruiser USS Springfield sailed behind. Overhead, a squadron of P-38 fighters provided air cover.⁸

Despite the high seas and inclement weather, FDR spent the first hour of the voyage taking in the sights as the ship passed the busy harbor and the bay beyond. (To facilitate FDR’s movement between decks, two special elevators had been installed on the Quincy.) At approximately 1:15 p.m., the task force increased the ship’s speed to 22.5 knots and started to zigzag—a standard anti-submarine maneuver. Although it was possible for the Quincy to receive messages, the U-boat threat also made it necessary for the task force to maintain radio silence. Hence, any outbound communication with Washington, London, and Moscow was possible only when one of the escorting ships broke away from the group to send a message.⁹

Gloriously cut off from the world, FDR settled into a day-to-day routine that included informal conversations with Admiral Leahy about the agenda for the coming conference, midday and evening meals taken in the company of the rest of his immediate party, and an after-dinner movie in Anna’s quarters. Aside from his talks with Admiral Leahy, which did not extend beyond an hour or so, and the occasional dinner conversation during which the conference was brought up, he mostly avoided lengthy discussions or formal meetings. Instead, he concentrated on getting as much rest as possible.¹⁰

Still, even in the middle of the Atlantic, it was not entirely possible to escape the exigencies of his job. On Wednesday, January 24, the president received word of a strike among the workers of the Bingham and Garfield Railroad, which served as a vital link between the massive open-pit copper mine at Bingham Canyon, Utah, and the mine’s smelters roughly twenty miles distant. Given that copper was crucial to the manufacture of ammunition and other critical war materials, a strike was out of the question. Hence, amid a driving rain and rough seas, FDR ordered the destroyer Satterlee to break formation to transmit an urgent radio message to Washington, informing the War Department of his approval of an Executive Order authorizing the US Army to take over the railroad.¹¹

Technically speaking, it was James Byrnes, in his capacity as director of war mobilization, who conveyed the message to Washington about the president’s order—a somewhat ironic development given Byrnes’s earlier insistence that instead of accompanying the president to Yalta it would be better for him to remain in Washington to handle just such an emergency. As a man of considerable ambition and pride, Byrnes assumed that FDR would take full advantage of his time at sea to consult with him on the host of political and economic issues facing the nation after the war. But much to Byrnes’s chagrin, FDR did not avail himself of this opportunity.¹²

Initially, Byrnes believed the president’s tendency “to stay in his cabin most of the time” was due to a worsening cold that FDR seemed to have contracted at the moment of their departure. But the more Byrnes observed the president, the more he feared that FDR’s appearance reflected an underlying condition. Byrnes raised his concerns with Anna and Dr. McIntire, both of whom assured him that the president did have a sinus infection and a cold—but, as Anna put it, “He was not really ill.”¹³

Byrnes was not the only person on board who was alarmed at FDR’s poor appearance. FDR’s longtime political associate Edward J. Flynn also expressed concern, deeming the president’s physical condition “very bad.” Indeed, Flynn was “shocked at the toll that had been taken [on FDR] by years of labor.” At Yalta, his concern would be transformed into amazement when he noted FDR’s ability, through “a supreme effort of will,” to become “completely alive and alert to what was going on.”¹⁴

That FDR was completely “alive and alert” to the larger issues at stake can be seen in the fact of Flynn’s presence itself. FDR’s decision to bring Flynn—a veteran of New York City machine politics and a former chairman of the Democratic National Committee—to a conference with Winston Churchill and Joseph Stalin was a puzzle to the others in the party. The mystery surrounding Flynn’s mission was exacerbated by the secrecy FDR demanded, which included the requirement that Flynn not even fill out a passport application before their departure—a decision Flynn found more and more disconcerting as the days at sea went by. This soon became a source of great amusement for FDR; he brushed off Flynn’s concerns and took great delight in drafting an unofficial passport in the form of Letter Signed by the President, to which Flynn attached a photo of himself taken by the ship’s photographer.¹⁵

In fact, FDR’s lighthearted demeanor masked the entirely serious reason he had invited Flynn to the conference: as a Catholic politician in a multi-ethnic and multi-religious city, Flynn knew a good deal about how to bring a diverse group of constituents together around a common set of values. Always thinking about the future, and well aware that the issue of religious freedom was one of the key points of domestic opposition to the Roosevelt administration’s decision to recognize the “godless” Soviet Union in 1933, FDR had asked Flynn to attend the summit in the hope that he would be able to discuss this important question with both Stalin and Soviet Foreign Minister Vyacheslav Molotov. FDR was also convinced, he told Flynn, that there could never be a permanent peace unless the large Catholic populations in Poland, Lithuania, and the Balkans were permitted to practice their faith freely: hence he believed that the question of religious freedom would no doubt remain an important factor in whether the American public retained its positive wartime attitude toward the Soviets—an attitude that was already fraying as Moscow’s intentions in Poland became clearer. All of this was especially disquieting to the Catholic hierarchy in America, whose bishops had sent a vigorously worded letter to FDR in December 1944 arguing that “a strong stand for justice in our relations with the Soviet Union is a postulate for our winning of the peace and for setting up an international organization which will command the support of our people.”¹⁶

Mulling all this on board the Quincy, FDR decided that Flynn should not only meet with Stalin and his foreign secretary at Yalta but continue on to Moscow for further discussions, and that he should subsequently travel to Rome in an effort to encourage Pope Pius XII to seek an improvement in relations between the Holy See and the Soviet Union. The latter would not be an easy task given the pope’s staunch anti-communism and unequivocal support of the London Polish Exile Government with whom the Soviets had broken off relations.¹⁷

AS FDR TRIED HIS BEST TO RECOVER HIS STRENGTH IN HIS CABIN, Anna made the most of this highly unusual “cruise.” Part of her delight in the voyage was the result of her being granted the admiral’s quarters, which were located next to her father’s and included a bedroom, bath, and sitting room. Given that Admiral Leahy was aboard, Anna’s lodgings represented a breach of protocol, necessitated not only by her desire to remain close to her father but also by the fact that Captain Elliott Senn thought it inappropriate to lodge her on the lower decks where the men often ran around in their skivvies!¹⁸

By the third day out, Thursday, January 25, the task force was approaching the island of Bermuda, which allowed for an exchange of escort destroyers, as the smaller vessels could not hold enough fuel to complete the crossing. The exchange of ships also afforded the Quincy the opportunity to transfer to one of its sister ships a “mail pouch” that, once it reached Bermuda, would then be flown by air to Washington. The arrival of the new escorts would also mean that for the first time since their departure from Virginia, FDR and Anna would be able to receive mail.

Curious about the means by which the mail pouch would be transferred in such high seas, Anna asked the officer in charge if she could observe the procedure. Not one to be outdone by his daughter, FDR insisted “that he would like to watch, too!” For a man in a wheelchair, though, such a request is easier said than done. The handover would take place at the stern of the nearly 700-foot-long Quincy, and knowing FDR’s sensitivity to being seen in public in his wheelchair, his naval aide, Vice Admiral Brown, cautioned Anna that he did not think “the boss would like to be watched by all the gun crews and other members of the ship’s party.”

“This was no matter,” Anna argued, “as long as we ignore this and tell him that he will not be under the gaze of the entire crew but just a few sailors manning the gun emplacements.” Equipped with this fallacious argument, she and Brown wheeled FDR to the stern. Anna immediately began to wonder if she had made a huge mistake. Her father’s wheelchair, which he himself had designed to be as unobtrusive as possible, amounted to little more than a narrow kitchen chair with wheels attached. It had no arms and no brakes to lock it into place. The Quincy, virtually dead in the water, pitched wildly while FDR clung to the wire railing “for dear life,” watching in fascination as the mail was placed into an empty torpedo canister attached to a long rope and then dropped over the stern. Meanwhile, on board the destroyer, a small group of sailors perched on the bow flung a grappling hook forward to try to catch the canister, not securing it until the sixth attempt.¹⁹

The exchange of mail brought the first in a series of “disconcerting” messages that FDR received from Winston Churchill while crossing the Atlantic. These included a note from Harry Hopkins, who had been sent to London in advance of the Yalta conference to mollify Churchill, still fuming at Secretary Stettinius’s earlier criticism of British policy in Greece and Italy. In the letter, Hopkins reported that Churchill had expressed the opinion that “ten years of research… could not have found a worse place in the world” to hold the conference than Yalta. The prime minister nevertheless felt they could “survive” the experience “by bringing an adequate supply of whiskey,” which he understood is “good for typhus and deadly on lice which thrive in those parts.”²⁰

The second message, a more serious one, arrived by wire on January 26. In it Churchill conveyed his “great concern” regarding the “extreme difficulty” involved in reaching Yalta via mountain roads. Indeed, he was compelled to advise that two attempts made by a combined group of British and American officers “resulted in failure to pass mountainous track in blizzard,” with one British officer describing the journey as “a most terrifying experience.”²¹

Churchill’s cables, coupled with the fact that the American delegation had not yet received word from the US advance team, sparked considerable discussion about what sorts of conditions they would confront once they reached the Crimea. Yet FDR remained confident that all would be well. He tended to brush off many of Churchill’s concerns out of suspicion that the prime minister was still annoyed at Stalin’s refusal to meet somewhere in the much more accessible—and warmer—Mediterranean.²²

THE APPROACH OF THE GULF STREAM BROUGHT WARMER WEATHER and renewed air cover, provided by an escort carrier that had positioned itself ahead of the task force as the convoy entered the waters to the southwest of the Azores. These remote far-flung vestiges of the once-powerful Portuguese Empire held special meaning for FDR, for it was to these largely forgotten outposts that he took his first official trip overseas as a young assistant secretary of the Navy in the closing days of World War I. FDR was astonished by the abundance of flora and fauna that blanketed this rugged volcanic archipelago. It seemed to him that “anything” would grow in the Azores. “One sees bamboo next to English Oak and even White Pine,” he noted in his diary—“a wonderful scene” of picturesque villages, volcanic craters, and “deep blue lakes and springs that threw off clouds of steam.” Not wanting to forget the thrill he felt as “his ship,” the USS Dyer, first made its way into the harbor of Ponta Delgada, the administrative capital of the Azores, FDR commissioned a painting of the scene that hung in his study for the rest of his life. In more recent times, he even entertained the thought that the Azores might serve as the headquarters for the Trusteeship Council of the United Nations.²³

In keeping with his ardent desire to get away from the day-to-day pressures of the Oval Office, FDR had left his key aides and staff with strict instructions not to bother him during the voyage unless it was a matter of extreme importance. It would not be long, however, before the tranquility FDR enjoyed at sea was disturbed by news from Washington—now becoming more accessible as the slate of escort vessels changed with greater frequency. Once again, the matter at hand concerned a domestic issue: on Monday, January 29, FDR received a long telegram from Samuel Rosenman informing him that Henry Wallace’s confirmation as secretary of commerce appeared “doomed.” Rosenman urged FDR to tell Congress that he would transfer the federal lending agencies out of Commerce, as Wallace’s critics had insisted. Otherwise, Rosenman insisted, there was no chance that Wallace would be confirmed. And even such a transfer might not be enough to save him. A missive from Eleanor received two days later more or less made the same case.²⁴

Keenly aware of the pressure that FDR was under due to the urgent demands of the war, Admiral Leahy was of the opinion that the president “is now faced with too many difficult and vital international problems to permit his getting into an acrimonious disagreement with the Congress, or even to warrant his being bothered by the personal troubles of any individual.” Indeed, given the “equally impractical… idealistic attitudes” of both Eleanor Roosevelt and Wallace, Leahy regarded the president’s decision to nominate Wallace as a mistake and had little sympathy for Wallace’s plight. Leahy’s view was that FDR should let matters take their course and “accept the decision of the Congress” whatever the outcome. But unwilling to abandon his former vice president, FDR sent word back to Samuel Rosenman indicating his support for the pending resolution.²⁵

On Tuesday, January 30, FDR celebrated his sixty-third birthday. To mark the occasion, the crew presented him with a special gift: a brass ashtray fashioned out of a five-inch shell casing fired during the Normandy invasion. Anna organized a small convocation that evening. Five cakes were baked for the occasion; the first four represented FDR’s four terms in office, and the fifth, procured at the last minute, was graced by a large question mark to represent the possibility of a fifth term, which brought hails of laughter from FDR. Unbeknownst to his assembled guests, FDR also enjoyed a more private celebration in his cabin that day, when Anna presented him with a series of little gifts and trinkets from Lucy Rutherfurd and his cousin Daisy.²⁶

Now more than a week at sea, the task force was nearing the North African Coast and the Strait of Gibraltar. Passing through the strait, which is a mere nine miles wide at its narrowest point, would be the most dangerous moment of the entire voyage. Adding to the captain’s concerns, on two occasions in the past forty-eight hours the escort destroyers believed they had detected a submarine in the vicinity, which raised the possibility of a security breach concerning the likely route of FDR’s vessel and the location of the conference.

The responsibility of maintaining the safety and security of the Yalta party fell to Vice Admiral Brown. Fit, trim, and born the same year as the president, Brown first met Roosevelt in 1912, shortly after the latter had been appointed assistant secretary of the Navy. Brown went on to a distinguished naval career and for a brief time served in the White House as a naval aide to President Calvin Coolidge. In 1934 he returned to the White House to take up the same position for FDR; however, in accordance with the normal rotation between sea and shore duty, he was offered the command of the Atlantic Fleet in the summer of 1936—a move that FDR enthusiastically endorsed, telling Brown: “You are the luckiest man on earth. I would give anything in the world to change places with you.”²⁷

The bond that FDR and Brown shared became even stronger when the latter returned to the White House yet again to resume his duties as naval aide in February 1943. By this point, active duty experience had imprinted on Brown the value of secrecy for a vessel plying the Atlantic. Brown repeatedly stressed the importance of maintaining an absolute lockdown on any information regarding the president’s voyage aboard the Quincy. Adding to his anxiety was the somewhat “lukewarm” attitude that FDR seemed to hold about the dangers involved. Brown was upset, for instance, when FDR sent the members of a Secret Service detail ahead as an advance team because they were always in pictures taken of the president and might be recognized abroad, providing a clue as to where and when the president might be meeting with the other members of the “Big Three.”²⁸

Brown was equally alarmed when he overheard Harry Hopkins explain that he would be traveling ahead of the party to London, Paris, and Rome for meetings with Churchill and de Gaulle before joining the president at Malta. This, too, might alert the enemy. More problematic still, Hopkins wanted to use the president’s plane. Unable to contain his worry, Brown confronted Hopkins with the demand that he use the president’s aircraft only as far as Gibraltar and then switch to a regular army transport to finish what Brown called a “most unfortunate venture.”²⁹

In the interests of security, Hopkins had received strict instructions to keep his mission to London secret and to say nothing to the press while he was in Paris or Rome. But as the task force steamed ever closer to the strait, report after report arrived about Hopkins’s activities in Europe, including numerous press pieces and radio broadcasts describing his itinerary. These notices included rampant speculation that his presence in London, Paris, and Rome was part of the administration’s effort to send key advisers aboard in advance of another meeting of the “Big Three.” Hopkins also made himself freely available to reporters and even staged a press conference in Rome on the evening of January 29, during which he all but admitted that a meeting of Churchill, Roosevelt, and Stalin was imminent.³⁰

On board the Quincy, news of Hopkins’s parley with the press infuriated FDR’s press secretary Stephen Early, upset the president, and seriously alarmed Brown, who felt that Hopkins’s interviews seemed “to give warning that something was going on in the Mediterranean.” To make matters worse, US naval intelligence had determined that German U-boats had indeed taken up positions in and around the strait. Whether this was a coincidence wasn’t known, but there can be no doubt that tensions ran high on the bridge in the wee hours of Wednesday, January 31, when Captain Senn spotted the historic Cape Spartel Light on the north coast of Morocco that marked the entrance to the strait.³¹

To reduce the chances of even a “lucky hit” by a U-boat, the chief of US naval forces in the Mediterranean had increased the Quincy’s stable of escorts to six destroyers and a light cruiser. He also ordered a pair of the famous “Black Cat” Catalina Flying Boats to provide nighttime air cover. In addition, a K-Class Navy Blimp equipped with sonar flew above the strait ahead of the force. In the meantime, Captain Senn increased the speed of the task force, still zigzagging, to an extraordinary 30 knots.³²

Just after 4:00 a.m., underneath a bright but waning moon, the task force finally entered the narrow waters that separate Europe and Africa. Having never sailed through the famous passage before, Anna decided that despite the hour she wanted to witness the occasion. From the flag bridge, as her father slept soundly below, she was able to make out the Rock of Gibraltar in the moonlight, the twinkling lights of the British naval base, and even the outline of a hospital ship. On the opposite shore was the stunning sight of Tangier, where it seemed that “every light in the town were lit.” As dawn broke, the snow-covered mountains of the Spanish coast came into view, followed by the outline of the rugged North African shore near the Spanish enclave of Ceuta.³³

Thursday, February 1—the last full day at sea before the landing at Malta—brought more warm weather. In an effort to conserve his strength before arriving at the ancient port of Valletta, FDR spent most of the afternoon on deck lounging in the Mediterranean sun. At home in Rhinebeck, meanwhile, his cousin Daisy waited anxiously for any word from “F” while she tended to his beloved Scottie, Fala. Due to the various communication restrictions placed on the presidential party, it would be some time before Daisy received a note from FDR. It came in the form of a brief diary that FDR had penned for her, sketching out his day-to-day routine and some of the high points of the voyage. Knowing that Daisy would be concerned about his health, FDR dutifully reported that he had made a point of getting plenty of rest. But the brevity of his descriptions and the overall lack of detail seemed uncharacteristic of him. His note showed none of his usual vitality, perhaps reflecting some of the dread he felt about the responsibilities he would soon confront as the relative quiet of his time at sea came to an end. “An awful day ahead,” he wrote as the Quincy finally reached Malta on the morning of February 2, 1945, before “tonight at 10, we are off by air for the final destination.”³⁴