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The Asian giant had a powerful hold on the president’s imagination— one that shaped his wartime policy for the worse.

Tourists trudging through the Roosevelt family seat in Hyde Park, New York, pass by Ming vases, a dinner gong, and porcelain elephants—lasting evidence of the family’s deep, long-ago ties to China. Franklin D. Roosevelt’s grandfather, Warren Delano II, had gone there in 1833 and made a fortune in the tea and the opium trade, the latter infinitely more profitable. He came home to America, lost his fortune in more respectable enterprises, and went back and made another fortune.

These riches underwrote a lavish lifestyle for FDR’s mother, Sara Delano Roosevelt, and her eight siblings. The family occupied a sumptuous villa overlooking Hong Kong Harbor, staffed by platoons of Chinese servants whose language Warren Delano forbade his children to learn. Later, as a mother, Sara would stir in her highly imaginative only child a nostalgia for a world he would never see yet never forget. The Delano roots left an indelible mark on the future president. “What vitality I have is not inherited from the Roosevelts,” he once admitted. “Mine, such as it is, comes from the Delanos.”

The Delanos’ Asian connection also gave the president a vicarious belief in his expertise on China. He once told his treasury secretary, Henry Morgenthau Jr.,“I have a background of little over a century in Chinese affairs.” Roosevelt believed that the most populous nation on earth, with a culture stretching back more than 5,000 years, belonged among the other great powers, and that it could be a strong American ally. But his sentimental, romanticized vision of China led to the creation of semidelusional policies toward that country—policies that, over the span of the war, cost much and gained little.

From the outset, Japan’s barbarism in its war against China outraged Roosevelt—the Rape of Nanking, the bombing of defenseless cities, the strafing of civilian refugees as if for sport. Well before America entered World War II, the president entertained schemes to bomb Japan. The Lend-Lease bill he maneuvered through Congress in March 1941 to make America “the great Arsenal of Democracy” was intended to prop up a beleaguered Great Britain, but FDR soon swept China in as an arms beneficiary.

Just two weeks after the attack on Pearl Harbor, the president began considering how to put spine into the 5.7 million strong—but battle averse—Chinese army of Generalissimo Chiang Kai-shek. Major General Joseph Stilwell, an ornery cuss with a biting tongue that had won him the nickname Vinegar Joe, found himself snatched overnight from his West Coast command and summoned to Washington. Though FDR did not know Stilwell personally, he allowed himself to be persuaded by Morgenthau and Secretary of War Henry Stimson that Stilwell was just the soldier to lead China’s legions for Chiang.

Stilwell was an old China hand, with four earlier tours of duty in that country, beginning in 1938 as military attaché to the American embassy. He had met the Generalissimo at that time, and quickly judged him as “utterly ignorant of what it means to get ready for a fight with a first class power.”

Vinegar Joe had his first meeting with FDR at the White House on February 9, 1942. It was not love at first sight. As Stilwell recorded in his diary later that day, the president monopolized the conversation, rambling on about his love of China and embellishing his monologue with stories of his mother’s life there. Stilwell, a staunch conservative, failed to succumb to the legendary Roosevelt charm, and wrote that he found his commander in chief “just a lot of wind.”

Chiang initially appeared receptive to Stilwell when the general arrived in China in late February, assigning him nominal command of certain divisions. The honeymoon, however, was short lived. The Generalissimo fired off orders to his generals without informing Stilwell—even countermanding him. “You see,” one of Chiang’s commanders admitted, “we Chinese think that the only way to keep the Americans in the war is to give them a few commands on paper.” Chinese generals ignored Stilwell while they pursued what seemed to be their primary mission: enriching themselves. As the Americans later learned, a unit commander would receive the payroll for his men and decide how much to dispense to them—and how much to keep for himself. Another favorite scheme was exorbitantly padding the cost to the Chinese government of coffins for dead soldiers. Commanders kept most of the money and paid carpenters a pittance.

The next February found a hopeful FDR awaiting the report of his Army Air Forces chief, Lieutenant General Henry “Hap” Arnold, who had gone to assess the air war in China. Arnold’s observations included his view of the Generalissimo, who, he wrote, “does not impress me as being a big man,” and “casts aside logic and factual matters as so much trash.” Chiang’s only strategy, Arnold concluded, was “Aid to China! Aid to China!”

Despite these dreary assessments, FDR remained convinced that something could still be made of the dozing giant. He told U.S. Army Chief of Staff George C. Marshall that Chiang “after all cannot be expected to use the same methods we do. When Stilwell speaks about the fact that the Generalissimo is very irritable and hard to handle, upping his demands, etc. he is of course correct, [but] Stilwell has exactly the wrong approach in dealing with Generalissimo Chiang”: tactless and short-sighted.

One American whom the President believed did understand Chiang and the Chinese mentality was Major General Claire Chennault, who had led the American volunteer fighter pilots known as the Flying Tigers in China in 1941–42 and who now commanded the U.S. Fourteenth Air Force there. While Stilwell confronted Chiang, the flier wooed him. The two Americans, however, clashed from the start. Chennault had opened a brothel served by Indian prostitutes after noting the number of his men put out of action by venereal disease. “The boys have got to get it, and they might as well get it clean as get it dirty,” he reasoned. When the straight-arrow Stilwell learned of the enterprise, he exploded. American planes, crews, and gasoline were not intended for carting whores over the Himalayas, he charged. As Chennault’s nominal commander, he ordered the bordello shut down.

Niceties employed to boost troop morale did not trouble Roosevelt; all he wanted was a fighting China. During a May 1943 meeting in Washington with British Prime Minister Winston Churchill, he summoned Stilwell and Chennault to the White House to iron out their conflicts. The flamboyant Chennault charmed the president, who afterward told the pilot to skip channels and communicate directly when he had something important to say. But Roosevelt found Vinegar Joe as charmless as his moniker. At one point, a peevish Stilwell had written in his diary, “FDR doesn’t like me to call Chiang Peanut.” He further referred privately to the crippled president as Rubber Legs.

During this Washington conference, Stilwell had a brief private meeting with the president and the prime minister. When “I tried to speak my piece,” he wrote in his diary, Roosevelt waved him aside, and “Churchill kept pulling away from the subject [of China] and it was impossible.” Churchill later noted that “the accepted belief in American circles was that [Chiang] would be the head of the fourth great power in the world after the victory had been won”—a conclusion the prime minister did not share.

With no alternate representative to send in his place, FDR shipped Vinegar Joe back to China to continue prodding Chiang to fight. When career diplomat and China specialist John Paton Davies, then a military attaché to Stilwell, asked the president what he would do if Chiang fell, Roosevelt revealed his near-bottomless faith in China. He replied unhesitatingly that he would support whoever succeeded the Generalissimo.

During his summit meeting with Churchill in Cairo that November, the president invited Hap Arnold to visit the Sphinx with him. There he got another earful on Chiang. As Arnold later wrote, “We talked over the air problem and what I could give the Generalissimo. Each time I said I could increase their tonnage over the Hump to 8,000 tons, [Chiang] would reply, ‘I am not satisfied. I must have 10,000 tons.’ If I said I will build the lift up to 10,000, the Generalissimo would say,‘not enough. I want 12,000.’”Arnold’s advice to the president was:“Don’t take the demands of the Generalissimo too serious.”

By 1944, Japanese forces were falling back almost everywhere else. But as General Marshall pointed out, they were “overrunning eastern China and rapidly eliminating the air fields of the Fourteenth Air Force,” which the United States had spent untold millions to build. On April 3, his patience tried, Roosevelt fired off a radiogram to Chiang harsher than any he had ever addressed to a foreign leader. “It is inconceivable to me,” he wrote, “that your…forces, with their American equipment, would be unable to advance against the Japanese 56th Division in its present depleted strength. Your advance to the West cannot help but succeed.” Chiang failed to reply.

At the root of the impasse were two irreconcilable views dividing the Chinese leader from General Stilwell. As chief of staff to the Generalissimo, Stilwell assumed that he had been given genuine authority over Chinese forces. Chiang, on the other hand, saw the United States simply as his quartermaster corps, with Stilwell as the supply sergeant—expected to deliver, as Henry Stimson put it, “clouds of war planes and swarms of tanks…. But they would not help themselves.” From Chiang’s vantage point, the stance made sense. He assumed that the United States would defeat Japan whether his armies fought or not. Consequently, his primary objective was to stave off his real enemy: the Chinese Communists under Mao Zedong. With prescience, Stilwell noted in his diary,“If this condition persists, China will have civil war immediately after Japan is out.”

Several months earlier, Roosevelt—having concluded that the Chinese Communists under Mao Zedong were scrappier than Chiang’s Nationalists—had sent the Generalissimo a request.“It appears to be of very great advisability that an American observer’s mission be immediately dispatched to North Shensi and Shansi provinces”—both territories under Mao’s control— to conduct intelligence operations.“May I have your support and cooperation in this enterprise?”he had asked. Chiang held off his reply for almost two weeks. When he did answer, he said that of course he was ready to support a mission in the north, but only in“areas where the political authority of the national government extends or wherever our army is stationed.” In other words, he wanted no Americans in contact with the Communists.

As Stilwell noted,“We were fighting Germany to tear down the Nazi system—one party government, supported by the Gestapo and headed by an unbalanced man with little education.” He found the situation in China little different: one-party rule in Chiang’s Nationalist Party, a Chinese Gestapo under Chiang’s intelligence chief, Dai Li, and a government “headed by an unbalanced man with little education.”

Through the fall of 1944, Japanese advances continued in China. Critical airfields fell to the enemy and still Chiang failed to fight back. FDR’s next communication to the Generalissimo adopted the hectoring tone of a Hyde Park squire dressing down a wayward gamekeeper. “I have urged time and again in recent months that you take drastic action to resist the disaster which has been moving closer to China.” He warned that China was lost unless Chiang placed “General Stilwell in unrestricted command of all your forces.” Chiang replied that giving Stilwell so much power would incite mutiny in the Chinese army.

To George Marshall, the sinkhole that Chiang ruled affected the war effort well beyond China’s borders. He told the president that the aid squandered on China “has been done at a heavy cost to our effort in other theaters,” most critically in Europe, where General Dwight D. Eisenhower needed more air power “to secure the Rhine crossings…, which involves the lives of American soldiers.”

China had Roosevelt in a bind. The president knew by now that Marshall and the impolitic Stilwell were right about Chiang. But he faced re-election in November 1944 and the China Lobby wielded political power in the United States. He could not appear to be abandoning the Generalissimo, a leader who had been portrayed to the American people in the news media as a valiant soldier and statesman. Nevertheless, the disastrous Chiang-Stilwell marriage could not continue.

In mid-November, Marshall informed Stilwell that FDR was going to give him the boot. “You will be ordered home,” Marshall wrote. No public announcement was to be made of his dismissal, and Vinegar Joe himself was to “make no comment.” Pestered by reporters as to what had really happened between Chiang and Stilwell, an impatient Roosevelt brushed the question aside, calling it “just a case of personalities.” What he could not say was that the United States had poured over $380 million in Lend-Lease aid to China (equivalent to billions in 2012), had provided a fighting American general to inspire Chinese forces—and had nothing to show for it.

Ironically, China was to become a great power one day, but not as Roosevelt had imagined. He had been dead nearly five years when, in 1949, the Chinese Communists took over a China that would eventually become a world player and an economic giant, if hardly the American ally that the president had dreamed about.


Originally published in the August 2012 issue of World War II. To subscribe, click here.