A Brief Biography of Chiang Kai-Shek:  The Misunderstood Nationalist Leader of China







“Seek truth from facts.”  -Chinese Proverb

Imagine losing the most populous country on earth.  That would not look good on a resume.  This was the fate of Chiang Kai-Shek (nicknamed the Generalissimo), the Nationalist Leader of China from 1927-1949 who lost the Chinese Civil War to Mao’s communists.  History doesn’t tend to look kindly on losers and even today Chiang is often regarded with less favour than Chairman Mao who may have killed more people than Hitler and Stalin.

Myths and Historical Context:

However, many of the negative perceptions of Chiang have been shown to be myths thanks to more than a decade of scholarship via books like The Generalissimo by Jay Taylor, Forgotten Ally by Rana Mitter, and China at War by Hans Van De Ven.  Rather than being corrupt Chiang ate and drank simply, lived a Spartan lifestyle and constantly upbraided less scrupulous subordinates.  Often dismissed as incompetent Chiang made great strides towards modernizing China during the Nanking Decade, scored diplomatic triumphs to put China back amongst the great powers, began the road to Chinese unity and kept the country together during 8 years of hell fighting the Japanese (1937-1945).  Accused of preferring to fight the Chinese Communists (the CCP) rather than Japan throughout the conflict it was actually the other way around as Mao let Chiang’s forces do the lion-share of the fighting, and dying, while the CCP laid low and built up strength for the postwar showdown with the Nationalists (the KMT).

Chastised by the Americans for supposedly doing little with the lend-lease they provided to China Chiang in reality received a tiny amount of it compared to Britain and Russia while American promises and commitments to China were watered downed or broken from Pearl Harbor to Yalta (at Yalta America agreed to let Russia have heavy influence in Manchuria behind China’s back).  A generation of American and Westerners including Joseph Stilwell, Margaret Tuchman, liberal correspondents, fellow travelers and “useful idiots,” have attempted to discredit Chiang’s reputation for decades with much success.  By contrast inconvenient truths such as America giving Japan far more weapons and resources than to China from 1937-1941, or the imperious and haughty attitude of American officials, including President Roosevelt, towards China at the time are less acknowledged.

Perhaps best known as “the man who lost China” much of the tone of Chiang’s detractors suggests he had countless advantages which he inevitably bungled to lose China and then was forced to flee to Taiwan to live out the rest of his days in ignominy.  A more objective analysis suggests Chiang Kai-Shek had too many enemies to fight and too many problems to tackle.  Chinese warlords constantly challenged his authority and progress, Japan attacked his regime on and off for nearly a decade then attempted to conquer China outright, and Mao’s small but disciplined communists provided the only real, viable alternative vision for the Chinese Nation.

Other countries were hardly more accommodating.  To say Stalin’s policy towards China was cynical would be an understatement.  The Soviet Union backed Chiang’s nationalists in the early 1920s (planning to betray them), then switched support to the CCP during the Nanking decade, later provided weapons to Chiang during the first part of the Second Sino-Japanese War to keep Japan from eyeing Siberia, cut off this crucial support in early 1941 after signing a non-aggression pact with Japan, and hedged its bets after World War Two by signing a peace treaty with Chiang while also providing support for the CCP.  As seen above, American hypocrisy towards Chiang was rife and when they finally started providing a good flow of weapons and material to his regime AFTER World War 2 they soon discontinued it in the subsequent last phase of the Chinese Civil War, abandoning their erstwhile ally to his fate as it did so later in Vietnam.

Besides this, Chiang ruled China only nominally upon coming to power in 1927.  Despite theoretical unity, the warlords and communists controlled much of China, the infrastructure, industry, and economy were backwards and sometimes nonexistent compared to the West and Japan.  Chinese education, technology, or even a sense of nationalism was limited outside of bigger cities such as Shanghai, Beijing, Wuhan and Guangzhou.  The countryside, then as now, was relatively poor and neglected (which gave Mao his decisive opening by cultivating Chinese peasants, 90% of the population at the time, as the vanguard of the revolution).  China’s military forces were divided between warlords, the CCP, and Chiang’s nationalists and were generally poorly trained, equipped, motivated, and led.  The old Chinese proverb “don’t waste good iron for nails or good men for soldiers” was hardly destined to be a wise philosophy against Japan’s samurai culture/hyper militarism that would result in the Rape of Nanking, millions of deaths and nearly 100,000,000 war refugees during the Second Sino-Japanese War.

Speaking of war and death there was far more of that during Chiang’s time on the mainland than the 8 year conflict against Japan.  Chiang’s Northern Expedition to unite China has been described as the largest military campaign in the interwar period.  There was of course the first (1927-1936) and second (1946-1949) parts of the Chinese Civil War.  There were countless conflicts amongst warlords, as well as the warlords attacking Chiang’s regime including the Central Plains War which probably saw more than 250,000 casualties.  There was also a brief Sino-Soviet War in 1929 over control of railways in Manchuria.

Japan was not exactly restrained before the Marco Polo Incident, which started all-out war in 1937 either.  In the preceding decade there were numerous “incidents” between China and Japan.  S.C.M. Paine noted the Japanese penchant to label skirmishes, battles, full blown wars, and even war crimes as “incidents.”  This is hardly surprising from a country that to this day continuously perverts its military history rather than face a harsh historical reckoning.  Japan’s rule of thumb could easily be “when it doubt deny and if you cannot deny minimize.”  What other country would call the Second Sino-Japanese War the “China Incident” or the Rape of Nanking the “Nanking Incident?”  Thus, there was the Jinan Incident in 1928, the Mukden Incident in 1931 (which saw Japan seize Manchuria), the Shanghai Incident in 1932, Japan’s Great Wall Campaign of 1933 and Japanese support of proxies fighting against KMT rule including an inner Mongolian leader with the unique name of Demchugdongrub.  Whatever can be said about Chinese history during this period you would not call it uneventful!

Against these multiple enemies and domestic issues, it is not surprising Chiang failed to tackle many of them but that he got anything done at all.  Unsurprisingly in such dangerous circumstances Chiang constantly had to guarantee the weak foundations of his regime.  Political survival is the first priority of any national leader and whatever Chiang’s flaws he became a master of this by striking quickly and decisively against threats, playing enemies (even subordinates) off each other, and relying upon an intelligence chief so vile he was nicknamed “China’s Himmler.”  Even his worst American critic, Joseph Stilwell, admitted that Chiang was “the most astute politician of the twentieth century.  He must be or he wouldn’t be alive.”


As for leadership qualities, Chiang’s toolbox was mixed.  He was generally calm during a crisis, great at analyzing geopolitical and diplomatic developments, was a model of discipline and frugality, and as Jay Taylor wrote knew “how best to play a weak hand.”  Given the disadvantages listed above he must have had many weak hands indeed.  On the other hand his leadership suffered from a propensity to micromanage, the willingness to take on too many roles (perhaps over 80 during wartime), often promoted officials based on loyalty over merit, his inability, or unwillingness, to clamp down on widespread corruption, and not adequately focusing on Chinese social and economic issues that would eventually undermine his legitimacy to rule China according to the Mandate of Heaven.

Chiang’s rise to power was no less colourful than his reign.  Apparently, he was a cantankerous, difficult child who relished war games and enjoyed ordering his classmates around.  The son of a salt merchant with some financial means he received the traditional Confucius education, studied for a while at a Chinese military academy and lived in Japan for a few years, learning Japanese and serving in Japan’s Army for a stint.  Disgusted by the decadent Qing dynasty during his youth he became a revolutionary and was involved in many of Sun Yat-sen’s (often depicted as the spiritual father of China on both sides of the Taiwan Strait) abortive and successful revolutionary coups.  Heeding the historical truth that “the enemy of my enemy is my friend” he would accumulate or expend allies when needed including revolutionaries, Shanghai gangsters, merchants and financiers, Russian, German and American advisors, temporary alliances with the CCP and the Soviet Union, Chinese warlords and landlords, etc.  If anyone ever needed an extensive rolodex it would have been Chiang Kai-Shek.

Sun Yat-sen maybe seen as China’s spiritual leader and Mao Zedong as the founder of modern China, but Chiang Kai-Shek was the individual to get the ball running.  Sun Yat-sen was charismatic and a visionary but he was a poor statesman, let alone politician.  He spent much of his time in China playing chess, planning railroads, and making ill-advised alliances with unscrupulous warlords who consistently outmaneuvered and outwitted him.  Mao Zedong was less honourable (to say the least) than Sun Yat-sen and ultimately outfought Chiang to win mainland China, but he was a relatively minor character in Chinese history until after World War 2 by which time Chiang had already done the lion-share of the work to unify, modernize and put China back on the world stage.  It was Chiang Kai-Shek who launched the Northern Expedition that would unify China (nominally at least) in 1926 and who presided over the Nanking Decade which saw unprecedented modernizing efforts and considerable economic, industrial, and infrastructure growth in the country.  He renegotiated customs duties and previously unfavourable agreements with the western powers, ultimately quashed the unequal treaties imposed by the West, and gave China diplomatic triumphs such as becoming one of the great four allies in World War 2 and gaining China a permanent seat on the United Nations Security Council.  He consistently outfought and eroded the influence of the self-interested Chinese warlords and steered China through the bloody, tragic, but eventually successful war against Japan.

However, despite all of this he miscalculated his chances against Mao’s communists in the postwar period, lost the last part of the Chinese Civil War and fled to Taiwan in 1949.  The worst part being that over a decade earlier Chiang was on the verge of annihilating the CCP while it licked its wounds from the Long March as it hunkered down in Yan’an in Shaanxi province (which could only be described as part of the boonies of China).  Chiang only needed to launch one last major effort against the CCP to crush it or push it across the border into the Soviet Union.  Instead, in what became known as the Xi’an Incident, he was kidnapped by some of his generals, including the playboy, opium smoking Zhang Xueliang, who wanted Chiang to fight the Japanese rather than fellow Chinese.  This was a popular sentiment in China, at least among the urban population, but it was naive given the relative strength Chiang had over the CCP but militarily weak position he had vis a vis Japan.  As S.C.M. Paine would sardonically remark in The Wars for Asia “China’s idealistic and privileged students got the war they demanded, fought by China’s legions of underprivileged peasant youth.”

In reality, Chiang was pursuing his longstanding policy of “internal pacification before external resistance” by trying to curb or eliminate the Chinese warlords and CCP to achieve real unity, build up strength, and then confront Japan later.  From a strategic and military point of view Chiang Kai-Shek was 100% correct regarding this, but Chinese domestic opinion and Japan’s occasional aggression against China made such a priority politically difficult.  During the Nanking decade he slowly built up the KMT’s military with foreign (usually German) aid and expertise for what he assumed would be a showdown with Japan after he crushed the CCP.  In reality, the Xi’an Incident and the outrage by Chinese students forced his hand to fight Japan in mid-1937 despite his German advisors stressing he’d need at least 2 more years to improve his army to have a chance of success.

The idea that Chiang Kai-Shek should, let alone could, have decisively confronted Japan’s military with any likelihood of success during his time on the mainland is quickly discredited by a serious study of military history for the time.  China had more territory and manpower than Japan, but that was its only advantages.  Japan was a unified country, had a strong economy and industrial base that could support strong, advanced armed forces, and a relatively educated populace eager to support the war effort.  China had none of this at the time.  Japan’s air force and navy completely outclassed the minuscule Chinese equivalents while Japan’s ground forces were supplied with far more, and usually better tanks, artillery, machine guns, and small arms.  Japanese divisions had considerably more troops, support services, firepower and its officers and soldiers were aggressive, motivated and usually better trained than the Chinese.  Despite Chiang’s efforts at unification and building armed forces during the Nanking decade a big percentage of the Chinese order of battle in 1937 were from warlords and the CCP who were seldom reliable or loyal to him.  Japan was also not above using chemical weapons against the Chinese which was continuously sanctioned by Emperor Hirohito himself.

Even Chiang’s best forces were not a 1 to 1 match for the Japanese and after years of lost battles it was calculated they would need a numerical superiority of 6-1 against Japanese forces to guarantee success in a stand-up fight.  As the war against China unfolded, Japan’s leaders estimated a Japanese regiment could take on even one the best Chinese divisions while a Japanese battalion could handle a more standard Chinese division.  Depending upon the Chinese forces they faced, it is thought Japanese divisions had 3-12 times the firepower vs. Chinese ones.  The historical record itself shows how often the Chinese were successful when fighting Japan.  During the Jinan Incident in 1928 the Japanese inflicted approximately 6000 Chinese casualties versus suffering 200 of their own.  In the initial fighting in Mukden in September 1931, which led to the annexation of Manchuria, Japan killed 500 Chinese while losing 2 soldiers.  Chinese forces likewise took disproportionate casualties at Shanghai in 1932 and during the Great Wall Campaign in 1933 and lost these contests as well.  

Even four years of relative peace between China and Japan (1933-1937), and Chiang’s considerable efforts to improve his military did not even the odds for the Second Sino-Japanese War.  In most battles numerically superior Chinese forces were routed with disproportionate casualty ratios from perhaps 4-1 at Shanghai in 1937 (one of the more hard-fought battles) to up to 20-1 or more during much of Japan’s Ichigo offensive in 1944.  China managed a few battlefield triumphs such as Taierzhuang in 1938, the first Three Battles of Changsha, and the Alamo like defense of Hengyang in 1944, but the general rule was Japanese operational victories and Chinese retreats.

Thus, the idea Chiang Kai-Shek should have concentrated on Japan rather than the CCP and had a good chance of beating the Japanese Army during the Nanking Decade was appealing, but ultimately naive, misguided and disastrous according to what actually happened.  In The Art of War Sun Tzu suggests “he will win who knows when to fight and when not to fight.”  Chiang knew it wasn’t time to fight Japan, but Zhang Xueliang and China’s idealistic students did not.

However, Zhang and the students got their way, Chiang was forced to ally with the CCP to confront Japan prematurely, China and Japan went to war the next year and the result was 8 years of destruction, rape, famine, floods, the overrunning of most of China’s main cities, railways, coastal areas, perhaps 14 million Chinese deaths, 100 million refugees, the evisceration of Chiang’s modernizing efforts during the Nanking Decade, the decisive weakening of Chiang’s regime, and the resurgence of a much stronger CCP.  Which of course helped result in the aforementioned CCP victory against Chiang in 1949 which left him with the crying trophy of Taiwan (at least it wasn’t Disappointment Island in the South Pacific).  In the end Chiang Kai-Shek was correct in believing that Japan, whatever its strength and ruthlessness could never overrun China but the CCP with its appealing (although false) ideology and discipline could and eventually did.  To paraphrase Chiang, Japan had been a disease of the skin, but the Communists were the disease that killed the heart.





After Chiang’s humiliating retreat to Taiwan many accounts of his life end but ironically it was his time on the island that would cement his legacy and later to a certain extent rehabilitate his reputation.  To be fair there were missteps such as the February 28th Incident of 1947 that witnessed the ruthless quashing of an anti-government uprising that saw at least 20,000 Taiwanese deaths.  Likewise, Chiang never instituted democracy, martial law existed throughout his reign, and while the white terror on the island may have been considerably lower (in numbers and in proportion to population) than Mao’s excesses on the mainland, but it was still an unforgivable blemish for his record.

However, without the countless external and internal enemies he had on the mainland, and with the superior infrastructure and conditions which existed on Taiwan, Chiang had more peace, flexibility, and opportunities for state building than during his tenure in mainland China.  As such he finally eliminated the widespread corruption in the KMT establishment, enacted widespread land reform, supported considerable industrial and economic growth which made Taiwan into one of the richest countries in the region, and did other civil and domestic initiatives which significantly improved the island nation.  While he never supported democracy, his son who succeeded him, began the process which would lead to Taiwan becoming one of the most free, open, and liberal democracies in Asia.  With the advent of democracy and more representation of the native Taiwanese population who had less love for the KMT than the Chinese who fled the mainland in 1949, Chiang’s reputation has suffered in Taiwan recently even as it has improved drastically in the west and even in mainland China!

Yet looking at Taiwan and China during the mid-1970s when Chiang and Mao died the Taiwanese model for China, and by extension Chiang’s legacy, comes off looking good by comparison to Mao’s.  Mao may have won the civil war, fought America to a standstill in Korea, made impressive strides in infrastructure, health care and other governmental initiatives, and gave China nukes.  However, regarding economics, industry, freedom, culture, and relative oppression, Mao’s China experiment was a failure versus Chiang’s Taiwan equivalent.  The countless Chinese murdered during land reform and the anti-righteous campaign, the tens of millions who starved to death during the Great Leap Forward, the Cultural Revolution that saw society tear itself apart, the traditional Chinese culture purged on the mainland, and the stagnation of industry and the Chinese economy which meant China’s stupendous economic takeoff was delayed for an entire generation are perhaps the 30% of things Mao did wrong (Deng Xiaoping once said Mao was “70 percent right and 30 percent wrong”).  By contrast Chiang’s relatively peaceful, prosperous, and increasingly positive rule in Taiwan appears superior indeed.

The fact Taiwan was in a good position to continue its successes and move towards democracy after Chiang died while Deng Xiaoping and his officials had to quash countless of Mao’s flawed policies before they could put China on the right path to stability and economic development (ironically by copying Taiwan’s economic model) suggests that in terms of ideology, governance and overall results, and since Mao’s communist vision with Chinese characteristics has been judged a failure by history, means Chiang’s Confucius and modern vision for Taiwan provides the superior China model.  China’s economy may still surpass that of America’s, but with its cynical blend of political communism and rapacious capitalism, along with demographic, cultural and social ills, China will probably become grey before it becomes rich and thus decline like Soviet Russia, and Japan before it (both of whom were assumed to eclipse America to superpowerdom eventually).  As Robert D. Kaplan once remarked:

History is a battle of ideas. Confucianism has triumphed over communism. Democracy and enlightened authoritarianism has triumphed over totalitarianism. And Chiang’s humanity, however imperfect, will triumph in Chinese minds over Mao’s epic cruelty.

Personality and Relationships:

That said, Chiang Kai-Shek was not always noble, let alone a particularly pleasant man.  As Simon Whistler, the host of Biographics, noted “while it’s tempting to hold him up as a saint compared to Chairman Mao being less of a colossal dick than Mao Zedong is kind of a low bar to clear.”  What was Chiang Kai-Shek’s character like?  Or what about his relationships and how he saw other peoples and countries?  Unsurprisingly these are as varied and conflicting as his successes and failures.

In his youth, he drank heavily, visited brothels, and was a womanizer.  As he aged, he settled down and enjoyed no drink, vices, and indulged in few luxuries despite his power.  Although dedicating himself to a disciplined version of Confucianism, he also converted to Christianity which he apparently took very seriously.  Indeed, he read the bible often, was fond of sermonizing his troops and officials, and even compared himself to Jesus Christ in his diary multiple times.  Despite this, he could be ruthless when he felt it necessary as seen by his decision to breach the Yellow River dykes in June 1938 to stem the Japanese advance which drowned at least 400,000 Chinese civilians.  Likewise, he ordered Changsha to be burned rather than fall to the Japanese the same year which was not only tragic as it killed 30,000 people but, ultimately pointless as the Japanese stopped short of the city.  While generally not as vindictive as the average dictator he was not above cruelty as seen by the unnecessary murder of one of the warlords (along with most of his family) who had kidnapped him during the Xi’an Incident, or the massacre of communists and labor activists alike in Shanghai in 1927.

As noted above, he was usually calm during a crisis but at other times, according to Brian Crozier, he could succumb to rage, yelling uncontrollably, pounding a table, or throwing a teacup at a bearer of bad news.  He once had a projectionist beaten simply because the hapless fellow showed him a film that offended him.  Perhaps more justly, on another occasion, he physically assaulted an officer he met who was leading conscripts along who were bound to each other by rope.  He was also prone to sobbing such as when he was severely chastised in 1926 for putting Canton under Martial Law, as well as when General Joseph Stilwell humiliated him, with the connivance of President Roosevelt and General Marshall, while trying to coerce Chiang to put all Chinese forces under the command of Stilwell in 1944!  That he was usually quiet, courteous, rigid, and controlled in most circumstances does not explain how quickly his emotions could change.  His supporters could call him “complicated” while detractors could suggest he was “emotionally unstable.”

One thing that should be stressed was despite his authoritarianism and flaws he was no Fascist.  Whatever Chiang was he did not advocate racial hierarchy, glorifying war, or a cult of personality.  That he had a tiny following of Blue Shirt Fascists and admired Germany’s disciplined society and military was one thing.  But there is no evidence he espoused the kind of expansionist, violent, and revisionist agenda Nazi Germany advocated.  According to his biographer, Jay Taylor, Chiang never praised Hitler or noted the Führer’s achievements in his diary (unlike many historical characters who later denied admiring Hitler).

That said, Chiang was not above stereotypes or prejudices.  Despite his time in Japan, serving in its army and admiring its orderly society, he had plenty of unkind words for the Japanese including calling them “dwarf pirates” and listing ways to kill them in his diary at one point.  For Chiang, the British were generally politically astute but cynical and the Americans the exact opposite.  Given Britain’s imperial history, Chiang’s diary has plenty of slurs against it including “how can we emancipate mankind if we cannot annihilate the English?”  After initially being snubbed by the British regarding his offer to provide troops to defend Burma after Pearl Harbor Chiang angrily replied “resisting the Japanese is not like suppressing colonial rebellions” and “for this kind of job, you British are incompetent, and you should learn from the Chinese how to fight against the Japanese.”

Chiang had interesting personal relationships as well.

He had 3-4 wives depending upon the source.  His first marriage was arranged when he was 14, he generally hated her, and it was rumoured Chiang beat her.  Yet he remained married for many years, even bearing a child with her out of loyalty to Chiang’s mother who threatened to kill herself if he divorced her.  Chiang got rid of her eventually and married a much younger girl, he was nearly 35 and she was 15, which appears reprehensible although such age gaps in marriage were not uncommon at the time.  What was definitely reprehensible was infecting her with syphilis (Chiang likely having contracted it from one of the many prostitutes he associated with in his earlier days) on their honeymoon!  Despite this, she was loyal and loving only to be dumped later in favour of his final wife Soong Mei-ling (often referred to as Madame Chiang Kai-Shek).

Madame Chiang Kai-Shek was in many ways the polar opposite of Chiang.  If he dressed simply and lived Spartanly, she was always flashy and enjoyed luxury.  Chiang appeared cold, aloof, even unworldly while she was gregarious, friendly and cultured.  Having been educated in America and speaking excellent english she provided him with good insight into the western world as well as being a charming ambassador and competent translator.  She also belonged to one of the most powerful, influential families in China and while they were in love there was no doubt a cynical calculation in his decision to dump his previous wife and marry Soong Mei-ling.  Much like Princess Diana, Madame Chiang Kai-Shek became a world celebrity and engaged in multiple philanthropic and charitable causes such as opening orphanages and visiting hospitals during the Second Sino-Japanese War.  Also, like Princess Diana she could be a prima donna and often succumbed to depression.  Unlike Princess Diana she didn’t have countless affairs and was loyal to her husband.  When Chiang was kidnapped at Xi’an in 1936 she went to join him in captivity and she stood by him throughout the whole war against Japan, the Chinese Civil War, and even after losing China.  No doubt not every husband would be so lucky!

Chiang had two sons:  Chiang Ching-kuo, from his first marriage, as well as an adopted son named Chiang Wei-kuo.  Perhaps illustrating Nationalist China’s constant switching of allies the former was sent to the Soviet Union to study while the latter went to Nazi Germany and temporarily served in the Wehrmacht.  Stuck in the Soviet Union when Chiang Kai-Shek betrayed the CCP (who were planning to betray him first) Chiang Ching-Kuo disowned his father and they were not reunited until Stalin brokered the Second United Front between the KMT and CCP in lieu of the Xi’an Incident a decade later.  Although Chiang initially favoured his adoptive, more attractive, son it was Chiang Ching-Kuo who would consolidate power in Taiwan after Chiang Kai-Shek died and would lead the island nation until his death in 1988.  Although a dictator like his father he did institute more freedoms and liberalization of society, as well as giving more opportunities to the native Taiwan population who had been neglected in favour of the mainland Chinese who had fled to the island at the end of the Chinese Civil War.  These actions put Taiwan on track to becoming the strong liberal democracy it remains today.

Perhaps Chiang’s most challenging relationship was not within his family, regime, or country but with an outsider:  General Joseph Stilwell, picked as the main American liaison to China after Pearl Harbor.  Whereas Mao Zedong is seen as Chiang’s arch nemesis Stilwell was unequivocally his most obnoxious and annoying antagonist.  Having the ear of General Marshall in Washington, controlling American lend-lease bound for China, and given the fact American policy regarding China during the war was simply to keep it in the fight to bog down the majority of the Japanese army with the least amount of financial and material investment possible, meant Stilwell had considerable leverage over Chiang, his titular superior.  This along with Stilwell notoriously difficult character (hence his nickname “Vinegar Joe”) made it inevitable his relationship with Chiang would be a tumultuous one.

Like Chiang’s complicated position in China which required considerable political and diplomatic acumen to deal with the countless factions and contexts involved Stilwell was given an extremely sensitive position in the overall allied war effort in World War 2.  The China/Burma/India theatre in which Stilwell was dropped into required considerable patience, understanding and diplomacy given the differing interests and visions China, America and Britain had in mind not only regarding the war effort but the future of Asia.  This isn’t even counting the Japanese who they were all supposed to be fighting!

Unfortunately, Joseph Stilwell was singularly incompetent to manage such a vital role as liaison between the Americans, British and Chinese for the war against Japan.  Hans Van De Ven, in China at War, provides a damning quote regarding Stilwell in this regard:

It did not help that General Stilwell was a difficult man.  With the exception of General Marshall, he held everybody in contempt, not just Chiang Kai-Shek (‘the Peanut’) or the Nationalist commander-in-chief He Yingqin (‘graced by no distinction in combat command’), but also, on the British side, General Archibald Wavell (‘a tired, depressed man pretty well beaten down’); General Alexander (‘astonished to find ME – mere me, a goddam American – in command of Chinese troops.  Extrawdinery!  Looked me over as if I had just crawled from under a rock’); and Mountbatten (one of the ‘Kandy Kids’, that is, someone enjoying life at the splendorous headquarters of South East Asia Command at Kandy on Sir Lanka).  His fellow Americans fared no better.  Stilwell could not stand General Chennault, of course, but he had as little regard for his successor, General Wedemeyer: ‘Good God – to be ousted in favour of Wedemeyer – that would be a disgrace.

He also sometimes referred to the wheelchair-bound President Franklin Roosevelt as “Rubber Legs.”

Stilwell had some laudable qualities such as having remarkable physical endurance for his age, not hesitating to speak truth to power, and most likely believed in his mission.  But his difficult personality meant he was all but impossible to work with and unable to take valid criticism, while his inability to understand the complexities of the political and social conditions in China dictated his relationship with Chiang would be untenable.  Thus, Stilwell’s command of Chinese troops in Burma in 1942 ended in disaster, that his refusal to provide Chiang and Chennault’s forces with material support (remember Stilwell controlled US lend-lease in China) would hinder China’s war effort in 1944, and that Stilwell’s arrogant emasculation of Chiang who was about to give him control of ALL Chinese forces in the latter part of that year arguably began the distrust and bad will that plague Sino-American relations to this day.

While it is tempting to at least suggest Stilwell was a gung-ho, old fashioned soldier willing to attack the Japanese head on history confirms him going AWOL during the Burma campaign in 1942, abandoning the Chinese forces Chiang had readily provided him.  Despite rejecting Chiang’s suggestion about adopting a defensive posture, and his advice regarding the proficiency of Japanese forces, Stilwell pushed through an attack, it went badly, the allies were routed, and Stilwell ran away and abandoned his troops.  Had he been leading an American unit he would have faced a court-martial.  Had he been a Chinese commander he would have faced a firing squad.  Instead, he turned abandoning his soldiers into the celebrated “March out of Burma” and wooed the press with his simple, tough talking language that magically obscured the reality of his incompetence.  Apparently, there is an equivalent to Donald Trump in every generation.

In the end Stilwell was fired and recalled but he found many allies and open ears to attack Chiang’s regime and up until the last decade his version of events in China has been the preferred one in textbooks, schools, and the media.  On the other hand, Chiang had some champions including the China Lobby in America and Time Magazine which had enough sympathy to put him on the cover 10 times.

Unique among great men of history Chiang had plenty of introspection and self-awareness. Despite being extremely Machiavellian, sometimes ruthless, and constantly composed in public his diary portrays a more self-critical side.  Perhaps this was a product of his combined Confucius, Christian worldview that stressed self-improvement and admitting one’s sins or maybe it was simply the case he was human enough to realize his many flaws.  Either way you wouldn’t see other historical leaders such as Winston Churchill, who once said “I am prepared to meet my maker.  Whether my maker is prepared for the ordeal of meeting me is another matter,” denigrate themselves as harshly as Chiang Kai-Shek.  It was hardly likely Hitler would have included “maybe I should have listened more to Guderian and Manstein” in the harangue that was his last will and testament.  By contrast as Andrew J. Nathan once wrote:

Chiang exceeded his critics in beating up on himself. In his diary, which he kept from 1918 until he was incapacitated by a heart attack in 1972, he berated himself as “ruthless and tyrannical; irritable; conceited; stubborn; wicked; … extravagant; jealous; stingy; lascivious; arrogant; full of sorrow and indignation.” The key to his character was patient revenge—the ability to “endure great humiliation” and prevail. Of course, striking that posture before the world was a sure way to look like a loser.

What if?:





Could Chiang Kai-Shek have consolidated his rule on the mainland and avoid being banished to Taiwan?  Like most questions regarding alternate history, it is more entertaining debating this than being able to provide a satisfactory answer.  It is easy, with hindsight, to point out mistakes and bad policies on Chiang’s part but not always easy to suggest what he should have done otherwise.  Given the many enemies, strained relations with other countries, and countless domestic issues Chiang faced it was not particularly easy to find ideal solutions much of the time.  For instance, attacking the CCP could lead him open to warlord and Japanese threats, or vice versa.  Trying to solve domestic issues such as land reform or confronting colonial interests could win over many Chinese but also alienate landlords, the western powers, and Japan.  Focusing on reforming his regime could have made it better at solving issues in the long-term, but risked considerable internal conflict even as the regime struggled to survive day by day against multiple enemies.

For most of his reign on the mainland Chiang was like a man juggling too many balls (the Japanese, Warlords, CCP, Americans and the Russians) in a violent windstorm (the many domestic ills facing China) while drunk (his own personal flaws).  In this regard Chiang could be compared to a functioning alcoholic who does better than expected in difficult circumstances, but whom we all know will fall flat on his face eventually. 

That said, what could Chiang Kai-Shek potentially have done differently?

Chiang failed to win over China’s peasants, partly due to relying on landlords as part of his powerbase, but mostly due to the CCP’s superior aptitude at winning over and mobilizing the rural population.  Perhaps better policies and more efforts could have borne fruit in this area, but it was always going to be playing catch up with the communists.  Likewise, the corruption and misdeeds of his regime which became worse after the Northern Expedition, and especially after World War 2, did Chiang no favours and his personal honesty and occasional chewing out of subordinates did little to alleviate this.  Chiang was always too focused on crushing the CCP and other enemies and assumed he could put off a severe overhaul of his regime until they were dealt with.  In the end, it compromised his regime from within, along with its chances against the CCP, and while he recognized this after fleeing to Taiwan it was too late to save the mainland.

He probably could have picked better officials and subordinates at many points and refrained from micromanaging those who were competent as well.  A better understanding of how media worked in a democracy like America could have given Chiang a chance against Stilwell and correspondents who won the battle of the narrative against him countless times.  Although China during his reign was remarkably open with much of the media critical of his regime it never had real power to topple Chiang or significantly change his policies.  As such, Chiang Kai-Shek’s attitude towards public opinion mimicked Frederick the Great who once said, “the people say what they like and then I do what I like.”

Regarding key decisions there are at least two that may have proven decisive had he chose differently.  In the aftermath of the Xi’an Incident, he could have ignored the agreement to ally with the CCP and instead launched a final offensive in early 1937 to crush them or kick them across the border into the Soviet Union.  Perhaps this would have displeased Stalin but given the latter’s overriding priority of having China distract potential Japanese aggression, and the Soviet leader’s constant cynical policies towards China, it is likely Stalin would have supported China against Japan in the subsequent war even had Chiang moved against the CCP in early 1937.  Either way at this junction Chiang decided to forego his best chance of eliminating the Chinese Communists and it would eventually prove costly indeed.

The second instance was after World War 2 when Chiang decided to go all in by trying to contest Manchuria with the CCP.  On paper, it looked possible given Chiang’s superiority in troop levels, population, territory, and temporary foreign aid.  In reality, his regime was broke, largely corrupt, and his soldiers and officers poorly motivated versus their CCP equivalents.  Realistically, Chiang could have held onto most of Southern and Central China, perhaps even much of the North, but Manchuria was a region too far.  Given the CCP forces’ main sphere of power was Manchuria, that the neighbouring communist regimes in the Soviet Union, Outer Mongolia, and North Korea could support the communists in Manchuria and given the sheer size of the region (as big as Western Europe) and its distances from Chiang’s powerbase in central China suggests it was overly ambitious for him to contest Manchuria.

Manchuria was a tempting prize due its significant industrial base (still the most extensive in China even after the Russians had dismantled and stolen much of it after 1945) and it would have been difficult not to fight for it for domestic reasons, but with hindsight, it would have been the right decision.  Chiang’s American advisors were against it due to military and logistical reasons and Chiang himself realized the potential risks but ultimately he went ahead hoping his larger, better equipped army could defeat the CCP and win the Civil War in short order.  In reality, Manchuria became a death trap for his forces who became bogged down in the cities at the end of tenuous lines of communication and surrounded by Mao’s forces in the countryside.  Chiang’s forces won many battles in Manchuria, but the CCP had the main advantages in the region and inevitably cut off the KMT garrisons in the cities and reduced them one by one.  By the time the communists took Manchuria Chiang’s best forces had been lost, his regime was thoroughly discredited at home and abroad, and the rest of China would fall to the CCP relatively easily.  

Thus, trying to fight for all of China, especially Manchuria, was folly when Chiang could probably have held onto most of the rest of it given the CCP’s weakness outside of Manchuria.  This would have given a rich and significant part of China to Mao, but much like the situation with North and South Korea, as well as West and East Germany, Chiang’s part of China was geopolitically stronger and with American aid it would have easily outperformed Mao’s Manchurian equivalent that would likely have stagnated into oblivion, or irrelevance, as these other communist regimes eventually did.  While much of this is speculation it was still more probable than winning a complete political and military victory over Mao post-1945.

The Jury is Out:

The question remains:  Was Chiang Kai-Shek a visionary leader who was overwhelmed by insurmountable odds or to quote Rana Mitter a “politically gifted but tragically flawed” leader who couldn’t rise above survival mode or his own shortcomings?  The truth is a combination of both.  Chiang’s vision regarding governance and society holds more currency in East Asia, China, and especially Taiwan than the all but discredited ideals of Mao Zedong.  The accomplishments Chiang managed in China and Taiwan were not inconsequential and were impressive given the circumstances he was presented with.  Indeed, there is no denying the bad luck, numerous enemies, and countess obstacles he faced.  As Paul H. Tai and Tai-chun Kuo have noted “ruling China and Taiwan for nearly half of a century, from 1928-1975, in an era of unprecedented international and domestic upheavals, the man must have possessed a level of administrative-military competence to meet the exigencies of his days and must have substantial achievements to warrant the support of his millions of followers.”

On the other hand, he usually put his loftier goals on hold, inevitably concentrating on ensuring his regime’s survival one day at a time and muddling through one crisis after the other.  Likewise, only Chiang, not his enemies or historical circumstances, can be held responsible for personal failings such as micromanaging, tolerating widespread corruption, neglecting social and economic issues in China, and a propensity to gamble in risky situations hoping either a lucky break, a turn of events, or an outside force would see him through.  Such gambles had eventually paid off during the Northern Expedition, his scuffles with Chinese warlords, the first part of the Civil War with the CCP, and even the conflict with Japan, but everything came crashing down afterwards when he went all in by fighting the communists over Manchuria.  There would be no Deus ex machina such as American intervention, or Stalin restraining Mao, to turn the tide in the last part of the Chinese Civil War.

Chiang’s reputation and legacy might be undergoing an overdue rehabilitation, and caricatures about him are slowly evaporating, but losing all of mainland China will always count against him.  History glorifies few who lose.  It may champion great generals who still lost like Hannibal Barca, Napoleon Bonaparte, and Erwin Rommel but not Chiang Kai-Shek.  Apparently losing China is in a whole other category than losing Carthage, France, or Germany!

Whatever one’s viewpoint on Chiang Kai-Shek what cannot be denied was his historical significance.  As Simon Whistler said after some harsh words regarding Chiang’s legacy:

What Chiang Kai-Shek was though was significant.  As the general who ended the warlord era, oversaw the Nanking decade, steered China through a Japanese invasion, and a civil war, then founded modern Taiwan, Chiang has an outsized impact on Eastern Asian history.  Perhaps more so than anyone else.

Likewise, Chiang’s importance was recognized throughout his career, even by rivals and enemies.  It wasn’t Sun Yat-sen who launched the Northern Expedition, Wang Jingwei (Chiang’s main political competitor) who managed the Nanking decade, or Mao Zedong who led the fight against Japan or overturned the unequal treaties with the western powers.  To prove a point Chiang was not above resigning to show when he was irreplaceable.  When his detractors in the KMT tried to outmaneuver him in the Northern Expedition, and in the aftermath of the Mukden Incident, Chiang temporarily stepped down and watched as others failed to govern and waited to be called back to power.  Stalin, who usually schemed against Chiang with the CCP, realized he was the only person who could lead China in a war against Japan; a reality that China’s warlords and even Mao Zedong had to swallow with considerable bitterness.  Churchill and the Americans concluded likewise despite many reservations they had about him.  Chiang realized all of this and in one of his less humble moments said “wherever I go is the Government itself.  I am the State.”

Perhaps it is fair to end with some words by Chiang Kai-Shek himself:  “If when I die, I am still a dictator I will certainly go down into the oblivion of all dictators. If, on the other hand, I succeed in establishing a stable base for a democratic government, I will be remembered forever in every home in China.”

Chiang did die a dictator and his democratic credentials were dubious to say the least, but his efforts did establish the conditions which allowed Taiwan to become a vibrant, prosperous democracy.  As China becomes more oppressive and belligerent under Xi Jinping, who has been confirmed as China’s leader for life, along with the likelihood China will become grey before it becomes rich, and the fact the China model with its ideologically barren mix of political communism and rapacious capitalism will ultimately prove unappealing and incapable of winning over people across the world over the admittedly imperfect, but still adaptive system of liberal democracy, the CCP’s vision for China and the world will eventually be consigned to the ash heap of history.  Whatever the last word on Chiang Kai-Shek in history will be there is every indication that his model for China (based on Taiwan) will prevail in the end.  That is a bet the Generalissimo himself would not have hesitated to take.


Biographics, “Chiang Kai-Shek:  The General who Created Modern China,” YouTube Video, 25:15, November 6, 2020, https://m.youtube.com/watch?v=fu8YCCA0UTI

Bix, Herbert P.  Hirohito and the Making of Modern Japan.  New York:  Harper Perennial, 2016.

Cowley, Robert.  What If?:  The Worlds Foremost Military Historians Imagine What Might Have Been.  New York:  Berkley Books, 2000.

Crozier, Brian.  The Man Who Lost China:  The First Full Biography of Chiang Kai-Shek.  New York:  Charles Scribner’s Sons, 1976.

Drea, Edward.  Japan’s Imperial Army:  Its Rise and Fall, 1853-1945.  Lawrence:  University Press of Kansas, 2009.

Eastman, Lloyd E.  “Who Lost China?  Chiang Kai-Shek Testifies.”  The China Quarterly, No. 88 (December 1981):  658-668.  URL:  https://www-jstor-org.libproxy.uregina.ca/stable/653752?seq%3D1=&seq=1#metadata_info_tab_contents

Fenby, Jonathan.  Chiang Kai-Shek:  China’s Generalissimo and the Nation He Lost.  New York:  Carroll & Graf Publishers, 2004.

Hays, Jeffrey.  (2015).  “Taiwan Under Chiang Kai-Shek and the Kuomintang,” [Online].  Available:  http://factsanddetails.com/southeast-asia/Taiwan/sub5_1a/entry-3800.html [2021, February].

Kaplan, Robert D.  (2014).  “Mao Won the Battle, Chiang Kai-Shek Won the War,” [Online].  Available:  https://foreignpolicy.com/2014/03/24/mao-won-the-battle-chiang-kai-shek-won-the-war/ [2021, February].

Kurtz-Phelan, Daniel.  The China Mission:  George Marshall’s Unfinished War, 1945-1947.  New York:  W.W. Norton & Company, 2018.

Military History Visualized, “Second Sino-Japanese War (1937-1945) – The Basics – featuring Justin,” YouTube Video, 1:02:57, July 10, 2017, https://m.youtube.com/watch?v=pMVc-w1orUM

Military History not Visualized, “The worst US General in World War 2?,” YouTube Video, 24:34, August 16, 2019, https://m.youtube.com/watch?v=TBNZqC3h_Y4&list=RDCMUChImwmytehS5SmlqMkXwoEw&start_radio=1&t=53

Mitter, Rana.  Forgotten Ally:  Chinas World War 2 1937-1945.  New York:  Houghton Mifflin Harcourt Publishing, 2013.

Nathan, Andrew J.  (2011).  “The Counter-Revolutionaries,” [Online].  Available:  https://newrepublic.com/article/85792/chiang-kai-shek-pakula-taylor [2021, March].

Ness, Leland and Bin Shih.  Kangzhan:  Guide to Chinese Ground Forces 1937-1945.  Solihull:  Helion & Company, 2016.

Paine, S.C.M.  The Japanese Empire:  Grand Strategy from the Meiji Restoration to the Pacific War.  Cambridge:  Cambridge University Press, 2017.

Paine, S.C.M.  The Wars for Asia 1911-1949.  Cambridge:  Cambridge University Press, 2012.

PBS, “China A Century of Revolution 1 China In Revolution 1911-1949,” YouTube Video, 1:53:18, 1989, https://m.youtube.com/watch?v=I5cl0GjPjy4&t=6035s

Peattie, Mark, Edward Drea and Hans Van De Ven.  The Battle for China:  Essays on the Military History of the Sino-Japanese War of 1937-1945.  Stanford:  Stanford University Press, 2011.

Spence, Jonathan D.  (2009).  “The Enigma of Chiang Kai-Shek,” [Online].  Available:  https://www.chinafile.com/library/nyrb-china-archive/enigma-chiang-kai-shek [2021, February].

Tai, Paul and Tai-chun Kuo.  “Chiang Kai-Shek Revisited.”  American Journal of Chinese Studies, Vol. 17 (April 2010):  81-86. URL:  https://www.jstor.org/stable/44288010?seq=1#metadata_info_tab_contents

Taylor, Jay.  The Generalissimo:  Chiang Kai-shek and the Struggle for Modern China.  Cambridge:  The Belknap Press of Harvard University Press, 2011.

The USAHEC, “‘China in World War II:  New History; New Perspectives for Today’ by Richard B. Frank,’” YouTube Video, 1:10:26, August 19, 2014 https://m.youtube.com/watch?v=bZREvulH55Y&t=225s

Van De Ven, Hans.  China at War:  Triumph and Tragedy in the Emergence of the New China.  Cambridge:  Harvard University Press, 2018.

Yiyao Alex Fan, “Chinese Civil War,” YouTube Video, 32:35, March 31, 2019, https://www.youtube.com/watch?v=M0L3XGrLWSg&t=1147s







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