Chiang Kaishek was born in Xikou, Fenghua, Zhejiang Province, China to Jiang Zhaocong and Wang Caiyu. He married Mao Fumei as arranged by his parents, and would have one son, Chiang Chingkuo (future president of the Republic of China) and one daughter with Mao. At this time, China was undergoing a tumultuous time; the monarch in Beijing was unable to hold the country together at the end of the Qing Dynasty, and foreign countries carved spheres of influence all along the coast. Chiang joined the call of the military in 1906 in hopes that he would be able to help the country. He attended Paoting Military Academy in China in 1906 and then studied at a Japanese military academy in 1907. He served in the Japanese Army from 1909 to 1911, and during this time he joined the movement to overthrow the Qing and set up a Chinese republic.

In 1911, the Wuchang Uprising marked the beginning of the Chinese revolution. Chiang returned to China as an officer in the revolutionary forces, and when the revolution was won, he was at the right place at the right time to become a founding father of the Guomingdang (Nationalist) Party that ruled the new republic. Dr. Sun Yat-sen, the visionary behind the new republic's constitution, took in Chiang as his protégé; additionally, Chiang broadened his support by befriending the powerful criminal underworld boss of the Green Gang and a local warlord in Guangdong (Canton). Though officially the revolution was won and a republic was born, China was actually in a state of anarchy. In 1923, Sun moved his base of operations to Guangzhou, Guangdong in southern China and re-established his government with the aid of Comintern. In the same year, Chiang was sent to Moscow to study Russian political ideals. He returned to China in 1924 and took over the Whampoa Military Academy as its commandant. By 1925, he had already developed a small army of officers at Whampoa who were fiercely loyal to Chiang and not necessarily to the government.

Sun passed away in 1925, and Chiang maneuvered himself into the position of power. Naming himself the Commander-in-Chief of the National Revolutionary Forces, he launched the Northern Expedition in Jul 1926 that pushed his government's boundaries into the rest of China. Although the Chinese Communists had helped him in his attempt to unify China, in Apr 1927 Chiang decided Communist influence in his government was not what he wanted, and suddenly turned against them brutally around the time he established himself in Nanjing. In 1927, Russian advisors attached to him were expelled back to Moscow, and by Jun 1928 his troops took control of Beijing. China proper was, at least nominally, finally re-unified. Around this time, he took on the title Generalissimo. 

On 1 Dec 1927, Chiang divorced his first wife and married Song Meiling, the younger sister of Sun's widow. To please Song's family, converted to Christianity in 1929.

Dr. Sun Yatsen (seated) posing with He Yingqin, Chiang Kaishek, and Wang Boling, Whampoa Military Academy, Guangzhou, Guangdong Province, Republic of China, 16 Jun 1924	Chiang Kaishek as the commandant of the Whampoa Military Academy, Guangdong Province, China, mid-1920s	Chiang Kaishek with the graduates of the second class of the Whampoa Military Academy, Guangzhou, Guangdong Province, China, 6 Sep 1925	Portrait of Chiang Kaishek, 10 Jan 1927

Chiang Kaishek and Song Meiling, Nanchang, Jiangxi Province, China, Oct 1927	Wedding photo of Chiang Kaishek and Song Meiling, Shanghai, China, 1 Dec 1927, photo 1 of 2	Wedding photo of Chiang Kaishek and Song Meiling, Shanghai, China, 1 Dec 1927, photo 2 of 2	Chiang Kaishek and Bai Chongxi, late 1920s