On March 10, Averell Harriman left New York for Britain aboard the Atlantic Clipper with his secretary, Robert Meiklejohn. The journey was slowed by weather delays in Bermuda and then by a backlog of passengers in Lisbon, where higher-ranking officials such as Ambassador Anthony J. Drexel Biddle Jr. took priority on onward flights. While Harriman waited in Estoril, Roosevelt signed the Lend-Lease Bill, Harriman briefly encountered Colonel Donovan, and Harriman made two small but revealing decisions: he sent out his clothes to be cleaned, and he bought a bag of tangerines for Clementine Churchill, knowing how scarce fresh food had become in Britain.

While Harriman struggled to reach England, Churchill faced worsening military pressures. Bulgaria joined the Axis, Germany moved closer to invading Greece, and Churchill chose to honor Britain’s commitments by sending troops to assist the Greeks despite the strain this placed on British forces in North Africa. At the same time, Erwin Rommel arrived in Libya with the Afrika Korps, and Hermann Gring launched heavy new bombing attacks on Liverpool and Clydeside, killing large numbers of civilians. These developments underscored the danger Harriman was coming to assess and the urgency behind Churchill’s need for American support.

Harriman finally flew from Lisbon on March 15, noticed a stark German aircraft on the tarmac, and reached Bristol five days after leaving New York. Churchill had arranged a personal gesture of welcome: Harriman was met by naval aide Tommy Thompson, flown in Churchill’s own Flamingo aircraft, and taken straight to Chequers in time for dinner. Churchill and Clementine greeted him warmly, and Clementine’s genuine delight at the gift of tangerines made the realities of rationing vivid to Harriman.

After dinner at Chequers, Churchill began a frank, strategic conversation that defined Harriman’s mission. Harriman said he could only help effectively if Churchill fully disclosed Britain’s condition and needs, and Churchill promised that nothing would be hidden. Churchill described the danger of invasion, but emphasized that the most immediate threat was the Battle of the Atlantic: U-boats, aircraft, and mines were sinking shipping faster than Britain could replace it. Harriman came away impressed both by Churchill’s resolve to continue fighting even alone and by Churchill’s blunt recognition that Britain could not achieve final victory without eventual American participation. Mary Churchill sensed that these talks marked a historic strengthening of Anglo-American ties.

Once in London, Harriman saw a city marked by both ordinary routine and recent devastation. He and Meiklejohn made lodging choices based on raid survival as much as comfort, and Meiklejohn noted that the blackout created eerie but often orderly streets. Harriman quickly built the Harriman Mission into a substantial office operation near the U.S. embassy, received a flood of social and political invitations, and began learning London’s wartime rhythms. A friendly note from David Niven showed how Britain’s public figures mixed military service with social life, while Harriman’s first press conference revealed that reporters found him attractive but overly cautious and formal.

The chapter closes on March 19, when Harriman joined Churchill for dinner in the armored basement dining room at 10 Downing Street. By then, Harriman had moved from distant observer to trusted intermediary, positioned to witness both the physical danger of Britain’s war and Churchill’s conduct under pressure at close range.