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Born in Zhejiang, Chiang received a military education in China and Japan and joined Sun Yat-sen's Tongmenghui organization in 1908. After the 1911 Revolution, he was a founding member of the KMT and head of the Whampoa Military Academy from 1924. After Sun's death in 1925, Chiang became leader of the party and commander-in-chief of the NRA, and from 1926 to 1928 led the Northern Expedition, which nominally reunified China under a Nationalist government based in Nanjing. The KMT–CCP alliance broke down in 1927 following the KMT's Shanghai Massacre, starting the Chinese Civil War. Chiang sought to modernise and unify the ROC during the Nanjing decade, although hostilities with the CCP continued. After Japan's invasion of Manchuria in 1931, his government tried to avoid a war while pursuing economic and social reconstruction.
Chiang grew up at a time in which military defeats, natural disasters, famines, revolts, unequal treaties and civil wars had left the Manchu-dominated Qing dynasty unstable and in debt. Successive demands of the Western powers and Japan since the Opium War had left China owing millions of taels of silver. During his first visit to Japan to pursue a military career from April 1906 to later that year, he describes himself as having strong nationalistic feelings with a desire, among other things, to 'expel the Manchu Qing and to restore China'.[12] In a 1969 speech, Chiang related a story about his boat trip to Japan at nineteen years old. Another passenger on the ship, a Chinese fellow student who was in the habit of spitting on the floor, was chided by a Chinese sailor who said that Japanese people did not spit on the floor, but instead would spit into a handkerchief. Chiang used the story as an example of how the common man in 1969 Taiwan had not developed the spirit of public sanitation that Japan had.[13] Chiang decided to pursue a military career. He began his military training at the Baoding Military Academy in 1906, the same year Japan left its bimetallic currency standard, devaluing the Japanese yen. He left for Tokyo Shinbu Gakko, a preparatory school for the Imperial Japanese Army Academy intended for Chinese students, in 1907. There, he came under the influence of compatriots to support the revolutionary movement to overthrow the Manchu-dominated Qing dynasty and to set up a Han-dominated Chinese republic. He befriended Chen Qimei, and in 1908 Chen brought Chiang into the Tongmenghui, an important revolutionary brotherhood of the era. Finishing his military schooling at Tokyo Shinbu Gakko, Chiang served in the Imperial Japanese Army from 1909 to 1911.
After learning of the Wuchang Uprising, Chiang returned to China in 1911, intending to fight as an artillery officer. He served in the revolutionary forces, leading a regiment in Shanghai under his friend and mentor Chen Qimei, as one of Chen's chief lieutenants.[14] In early 1912 a dispute arose between Chen and Tao Chengzhang, an influential member of the Revolutionary Alliance who opposed both Sun Yat-sen and Chen. Tao sought to avoid escalating the quarrel by hiding in a hospital, but Chiang discovered him there. Chen dispatched assassins. Chiang may not have taken part in the assassination, but would later assume responsibility to help Chen avoid trouble. Chen valued Chiang despite Chiang's already legendary temper, regarding such bellicosity as useful in a military leader.[15]
Chiang's friendship with Chen Qimei signaled an association with Shanghai's criminal syndicate (the Green Gang headed by Du Yuesheng and Huang Jinrong). During Chiang's time in Shanghai, the Shanghai International Settlement police observed him and eventually charged him with various felonies. These charges never resulted in a trial, and Chiang was never jailed.[16]

Clockwise from top-left: Chiang inspecting soldiers of the National Revolutionary Army; NRA troops marching north; an NRA artillery unit in combat; civilians showing support for the NRA; peasants volunteering to join the expedition; NRA soldiers preparing to launch an attack.
Chiang became a founding member of the Nationalist Party (a forerunner of the KMT) after the success (February 1912) of the 1911 Revolution. After the takeover of the Republican government by Yuan Shikai and the failed Second Revolution in 1913, Chiang, like his KMT comrades, divided his time between exile in Japan and the havens of the Shanghai International Settlement. In Shanghai, Chiang cultivated ties with the city's underworld gangs, which were dominated by the notorious Green Gang and its leader Du Yuesheng. On 18 May 1916 agents of Yuan Shikai assassinated Chen Qimei. Chiang then succeeded Chen as leader of the Chinese Revolutionary Party in Shanghai. Sun Yat-sen's political career reached its lowest point during this time—most of his old Revolutionary Alliance comrades refused to join him in the exiled Chinese Revolutionary Party.[17]

Sun Yat-sen and Chiang at the 1924 opening ceremonies for the Soviet-funded Whampoa Military Academy
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