「勇敢、誠篤、知兵事」是孫中山對蔣中正的評語。此一評語不僅反映出孫中山長年對蔣中正的觀察所得，也為蔣中正為何能得到孫中山的青睞，在眾多青年革命同志中脫穎而出，提供最佳的註解。 　　蔣中正的勇於任事，首見於辛亥革命時期刺殺陶成章一事。陶成章原為同盟會大老、光復會首領，蔣殺陶不是因他反革命，而是因為陶擬爭取浙江都督，有意取代滬軍都督陳其美在上海的地位。鑑於陳其美為孫中山嫡系，保陳就等於保孫，蔣的果斷決行因此得到陳、孫的肯定。 　　蔣中正的知兵事，和他的軍事學歷背景以及他在中華革命黨東北軍及護法時期粵軍陣營的實際歷練，密不可分。尤其當孫中山總結中國革命失敗的原因在於革命黨沒有自己的武裝勢力，認為今後革命黨應以培養自己武力為首務，蔣的知兵事便成為孫特別借重的原因。 蔣中正一生事業始於陸軍軍官學校，已不容贅言。而蔣之所以能出掌該校，孫中山的賞識實扮演關鍵性角色，且符合時代對新領袖實踐能力的需求。

“Brave, faithful, and a strategic thinker”—such was Chiang Kai-shek in Sun Yat-sen’s eyes. This comment shows clearly how Chiang Kai-shek won Sun Yat-sen’s attention and promotion in competition with other revolutionary youths. Chiang Kai-shek’s bravery was first shown in his assassination of Tao Chengzhang, one of the important members of the National Alliance (Tongmenghui) and the former leader of the Restoration Society (Guangfuhui). Chiang killed Tao not because Tao opposed the revolution but because of his interest in the Zhejiang governorship and his desire to replace Chen Qimei, Sun Yat-sen’s close comrade and military governor of Shanghai. Given that Chen Qimei was part of Sun Yat-sen’s faction, and that resolutely killing Tao Chengzhang was to protect Chen Qimei, which was thus to protect Sun Yat-sen, both men would approve of the assassination. 　　Chiang’s skills at military strategy derived from his experience of military leadership with Northeastern National Army and the Guangdong Army during the periods of the Chinese Revolutionary Party and the Constitutional Protection War. His expertise on military matters was quickly noticed by Sun Yat-sen, especially after Sun determined that it was their lack of military capacity that had doomed the revolutionaries to defeat. It is clear that Chiang Kai-shek’s political rise began during his headship of the Huangpu Military Academy. Sun Yat-sen’s approval was the key to Chiang’s becoming academy head. And in addition to Sun’s approbation, Chiang also fit the needs of the time for new leaders with practical abilities.