His military studies were terminated by the outbreak of the Republican Revolution in 1911. Chiang returned to Shanghai, and began a vigorous military career under the local military commander, pro-Sun in politics. Chiang himself had come into contact with the Republican-Nationalist group while in Japan. There was already no question of where his loyalties lay. He made rapid progress, and saw something of fighting. He took part in the abortive Second Revolution, of 1913, which was the military attempt by Sun Yat-sen and his first military coadjutant, Huang Hsing, to check Yüan Shih-k'ai and to save the newborn Republic by force. In this time, while the enthusiasm of his military studies had not yet worn off, Chiang wrote prodigiously. No Westerner has, so far as the present author knows, taken the trouble to go through Chiang's writings in order to study him. Chinese commentators praise them as full of military acumen, a sense of the novel and important forces in Chinese society, and a vigorous moralism—modern-military in form, but archaic in language—which animated Chiang's youthful desire to improve the world with good, technically apt gunfire. He was at this time twenty-three or twenty-four.
Between this early career and the later years of Chiang's life—the years in which his star rode incessantly ascendant—there is a gap of several years, 1913 to 1918. In this time Chiang lived a life primarily civilian, although he remained under the patronage of his first military leader, General Chen Ch'i-mei, murdered in 1915. Chiang went on a military intelligence trip for the Sun Yat-sen group, travelling through Manchuria in 1915. He opposed Yüan's moves, and stayed in close contact with the patriotic organization. Yet, the total picture of his life in these years lacks the connecting linkage which binds his childhood, his school days, and his mature career. His activity, while considerable, was diffuse.
He went down to Canton in 1918, and fought under the command of Sun Yat-sen, with the inferior troops and hopeless expeditions which the Leader, politically adept but strategically inexpert, kept throwing against the confusion of the tuchün wars, with the result that the war-lords, counting him as another element in their balance of power, did not even set up a united front against him. Chiang, a Central Chinese, was unsympathetic to the intense provincialism of the Cantonese, and was hopelessly tactless in criticizing old-type soldiers upon whom Sun then relied. Disillusioned but still loyal, he went back to Shanghai and wrote letters of advice to his friends in the South, including Dr. Sun. Throughout this time he was simply one more among the dozens of bright young military men who were, in the existing crudity of warfare, unneeded in China. (Chu Tê, Chiang's present colleague and rival who heads the Soviet Chinese military system, was at this time besotted in Yünnan—a petty war-lord of landlord family, trapped hopeless on his little island of power amidst ruin.)
The period in the Shanghai years was filled in with business activity. Chiang was acquainted with some of the most influential merchants of the city, among them the crippled Chang Ching-chiang, a Paris merchant whose personal wealth was an informal treasury of Sun's movement. Chiang entered brokerage, and is supposed to have made a great deal of money. He became acquainted with the modernized, Westernized young Chinese of the metropolis, and left many friends behind him among the Chinese business men and industrialists.
Speculative or unfriendly writers asseverate that Chiang joined the Green Gang, an association which combined the features of a protection racket and a benevolent society. (Such a society, common in China during periods of disturbance, is the archetype of the American-Chinese Tong [tang] in its more violent phases.) If so, membership gave Chiang the key to an underworld as well organized as François Villon's Paris, wherein beggars, thieves, pickpockets, kidnappers, labor contractors, burial societies, and legitimate associations merged under the extra-legal government of a Masonic-like hierarchy. (The author is acquainted with a Chinese League of Nations official who joined the Gang as a necessary implement of social research, and was afforded genuine courtesy in preparing a report, general but accurate as to prevailing conditions, through the assistance of his fellow-members.)
Chiang's marriage, which had been made Chinese-fashion in his late boyhood, had given him posterity—a son, now the pro-Communist, Soviet-trained Major-General Chiang Ching-kuo—but little companionship. His wife and son remained most of the time at his native home, whence he returned to see them and his mother, at Fenghua in Chekiang. Social contacts, acquaintance with capitalism, looseness of family connections, spasmodic work for the Revolution, and some military work—this, combined with the making and the losing of a fortune, fill the early maturity of Chiang.
He appeared upon the national and the world scene by his selection in 1923 to go to Moscow under the terms of the Nationalist-Soviet understanding, there to receive military training. He had definitely cast in his lot with Sun Yat-sen, making soldiery his vocation, and the selection implied that Sun began to see in him a military aide, to replace Huang Hsing of the first revolution. Chiang spent four months in the Soviet Union. The Communists, whom he was to fight six years later, showed him their combination of political and military warfare applied in Trotsky's Red Army. Chiang, already the beneficiary of Japanese training, had found Japanese military science dependent upon the framework of a stable constitutional system. In China his earlier training had been superior to its environment and did not have the practical utility of five years' banditry. Chiang, professional by spirit, restless under the drive of conscience and ambition, now found in Moscow the intermediate steps between modern warfare and government-building. He found that an army, from being the tool of pre-existing order, could become the spearhead of an accompanying order. Returning to China via the Trans-Siberian Railroad, he met General Galens (Vassili Bluecher), later his chief Soviet military aide at Canton.
In Canton, the first military creation on Soviet models was the Whampoa (Huangpu) Academy. Decreed by Sun Yat-sen, who made Chiang chief, the Academy had Soviet advisers, eager to instill revolutionary and civil-war techniques. Chiang began the development of a modern army, and the real accretion of his own power. Even before he commanded full armies, Chiang used his cadets to good purpose in actual combat.
From this point on, Chiang's career becomes a part of the military history of the revolution. In his earlier years of power, Chiang emerged to leadership by cooperating with various intra-Kuomintang groups. He stood with the Left and utilized the Communists, although he managed to provoke, suppress, and appease the Communists in a way which no one else managed. He led the victorious Northern Expedition in 1925-27, carrying his forces on the crest of the Great Revolution. He was little known, but seen to be ambitious, zealous, incalculable, and a political strategist of ruthless genius. He soon found himself one of the triumvirate of Sun Yat-sen's successors: Hu Han-min, the Right Kuomintang leader, editor of Sun's works; Chiang; and Wang Ch'ing-wei, the Left Kuomintang leader.
At Shanghai, in 1927, Chiang's troops turned suddenly against the Communists and Left groups, quenching the uprising which had taken the city under his flag. This coup was undertaken because Chiang felt that the Communists were outrunning their promises. The Soviet advisers, who had come to help the Nationalists, had professed their concern for China's national struggle, and for the desirability of a fight against imperialism. They had not told Sun himself that he was a mere precursor to the proletarian revolution, nor informed the Nationalists that they were being given the privilege of fighting a war to advance the historical necessity of Nationalist extinction, as the next step in China's dialectic progression. Trotsky talked openly in Moscow about overthrowing the Chinese revolutionaries, and hijacking the Chinese revolution with the Chinese Communists, while Stalin believed in appeasing the Nationalists longer before discarding them. Of this Chiang was fully aware, and he struck at the sources of Communist power, labor and peasant unions, using a ruthlessness comparable to theirs. He went further, establishing the National Government (in the five-power form) at Nanking, and leaving the Left Kuomintang uneasily in the company of the Communists at Hankow. When the Communists proceeded to debate the question of monopolizing the remnants, even the Left-Kuomintang had had enough. They suppressed the Communists, and dissolved, coming down river to Nanking and joining the new government, while Chiang stepped technically out of the picture to ease the healing of the schism. Chiang's legitimacy in the leadership of the Kuomintang and the Sun Yat-sen revolution is shown by the fact that within two years he had an overwhelming majority of the veteran Kuomintang leaders at his capital.