Chiang was born in Xikou, a town approximately 30 kilometres (19 mi) southwest of downtown Ningbo, in Fenghua, Zhejiang. However, his ancestral home, a concept important in Chinese society, was the town of Heqiao (和橋鎮) in Yixing, Jiangsu, approximately 38 km (24 mi) southwest of downtown Wuxi, and 10 km (6.2 mi) from the shores of Lake Tai. Chiang's father, Jiang Zhaocong, and mother, Wang Caiyu , were members of an upper-middle to upper-class family of salt merchants. Chiang's father died when he was only eight years of age, and he wrote of his mother as the "embodiment of Confucian virtues.
Baoding Military Academy, in 1906. He then left for the Tokyo Shinbu Gakko , an Imperial Japanese Army Academy Preparatory School for Chinese students, in 1907. There he was influenced by his compatriots to support the revolutionary movement to overthrow the Qing Dynasty and to set up a Chinese republic. He befriended fellow Zhejiang native Chen Qimei, and, in 1908, Chen brought Chiang into the Tongmenghui, a precursor of the Kuomintang (KMT) organization. Chiang served in the Imperial Japanese Army from 1909 to 1911.
Returning to China in 1911 after learning of the outbreak of the Wuchang Uprising, Chiang intended 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. In early 1912, a dispute arose between Chen and a dissident member of the Revolutionary Alliance who opposed both Sun Yat-sen and Chen, and who sought to avoid escalating the quarrel by hiding in a hospital. When Chiang located him, Chen dispatched assassins, and although he probably did not take part himself, Chiang later assumed responsibility in order not to get Chen in trouble. Chen valued Chiang in spite of his now legendary quick temper, thinking that such bellicosity was useful in a military leader.
After the success of the 1911 Revolution, Chiang became a founding member of the KMT. After the takeover of the Republican government by Yuan Shikai and the failed Second Revolution in 1913, Chiang, like his KMT comrades, divided time between exile in Japan and the havens of the Shanghai International Settlement. In Shanghai, Chiang cultivated ties with the city's underworld gangs, dominated by the notorious Green Gang and its leader Du Yuesheng. On May 18, 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 career was at its lowest point then, with most of his old Revolutionary Alliance comrades refusing to join him in the exiled Chinese Revolutionary Party.
In 1917, Sun Yat-sen moved his base of operations to Guangzhou, and Chiang joined him in 1918. At this time Sun remained largely sidelined; and, without arms or money, was soon expelled from Guangzhou and exiled again to Shanghai. He was restored to Guangzhou with mercenary help in 1920. After returning to Guangzhou, a rift developed between Sun, who sought to militarily unify China under the KMT, and Guangdong Governor Chen Jiongming, who wanted to implement a federalist system with Guangdong as a model province. On June 16, 1923 Chen attempted to assassinate Sun and had his residence shelled. During a prolonged skirmish between the troops of these opposing forces, Sun and his wife Soong Ching-ling narrowly evaded heavy machine gun fire and were rescued by gunboats under Chiang's direction. The incident earned Chiang the trust of Sun Yat-sen.
Sun regained control of Guangzhou in early 1924, again with the help of mercenaries from Yunnan, and accepted aid from the Comintern. Undertaking a reform of the KMT, he established a revolutionary government aimed at unifying China under the KMT. That same year, Sun sent Chiang to spend three months in Moscow studying the Soviet political and military system. During his trip in Russia, Chiang met Leon Trotsky and other Soviet leaders, but quickly came to the conclusion that the Russian model of government was not suitable for China. Chiang later sent his eldest son, Ching-kuo, to study in Russia. After his father's split from the First United Front in 1927, Ching-kuo was forced to stay there, as a hostage, until 1937. Chiang wrote in his diary, "It is not worth it to sacrifice the interest of the country for the sake of my son." Chiang even refused to negotiate a prisoner swap for his son in exchange for the Chinese Communist Party leader. His attitude remained consistent, and he continued to maintain, by 1937, that "I would rather have no offspring than sacrifice our nation's interests." Chiang had absolutely no intention of ceasing the war against the Communists.
Chiang Kai-shek returned to Guangzhou and in 1924 was appointed Commandant of the Whampoa Military Academy by Sun. Chiang resigned from the office for one month in disagreement with Sun's extremely close cooperation with the Comintern, but returned at Sun's demand. The early years at Whampoa allowed Chiang to cultivate a cadre of young officers loyal to both the KMT and himself.
Throughout his rise to power, Chiang also benefited from membership within the nationalist Tiandihui fraternity, to which Sun Yat-sen also belonged, and which remained a source of support during his leadership of the Kuomintang.