Cao Cao, the imperial general at the end of the second century and the beginning of the third century probably ought to qualify, as he came back from defeat to ultimate victory more than once, although his defeat at the battle of the Red Cliffs could be seen as relegating him to a lower status. However, given that he had started with a demoralized imperial army during the collapse of the latter Han dynasty, and faced powerful enemies, his mere survival was quite an accomplishment. China went into the three kingdoms period after that, and Cao Cao had managed to hang on to his territory in the north, which became one of the three kingdoms. Red Cliffs was a naval battle, which he lost while employing and army of infantry and cavalry with no naval exparience.
Among the Japanese, Oda Nobunaga should rate highly, but so would his erstwhile friend and ally, Tokugawa Ieyasu. They both flourished during the Sengoku, or warrring states period of the late 16th century. Tokugawa (né
Matsudaira) defeated the army of Takeda Katsuyori (himself an accomplished officer) in about 1600, finally ending the long strife which had lasted since about 1560. That era saw the collapse of the Ashikaga shogunate, and eventually resulted in the foundation of the Tokugawa shogunal dynasty, which would rule Japan for the next two centuries. It was the beginning of the Edo period, referring to Tokugawa moving the capital from Kyoto to Edo, modern day Tokyo. Both Oda and Tokugawa employed large numbers of firearms, and both were brilliant at manipulating the constantly shifting loyalties of other Daimyos ("great lords") in Japan. Oda Nobunaga, for example, destroyed the Mt. Hiei Buddhist monastery near Kyoto, ending the more than two centuries of domination of the Imperial bureaucracy by the monks--this period, in addition to being called the Ashikaga shogunate, was known as the Muromachi bakufu, referring to the district in Kyoto where the monks had their offices.
Oda was sufficiently adroit that, although having destroyed their home monastery, he employed a large force of those monks as sohei
, warrior monks, to fight for him against the Ikko Ikki, another Buddhist sect which constantly fomented peasant uprising, and bitterly opposed the introduction of western arms and technology. Finally cornered in their castle-monastery at Honganji, and supported by the militarily powerful Mori clan, Oda used the Mt. Hiei sohei
as shock troops and assault troops to finally bring them down. Oda subsequently drove from Kyoto the puppet Ashikaga Shogun whom he had installed eight years earlier, ending the Ashikaga or Muromachi period.
It is a toss-up which one would choose. Neither Oda nor Matsudaira/Tokugawa came from powerful clans, and in fact Nobunaga was the despair of the Oda clan before he emerged as a warlord. Tokugawa took many pages from Oda's book, but was otherwise a largely conventional leader--after the establishment of his shogunate, western firearms were banned in Japan, the Christians were driven from Japan and western trade was restricted to a small, set number of ships at Nagasaki each year.
Oda Nobunaga probably deserves the most credit. He so effectivly tread the treacherous path of clan loyalties and daimyo ambitions in 16th century Japan, and rose from almost nothing to the very height of power. He frequently instigated petty, local warfare which weakened his enemies, and he frequently employed other people's private armies (or, for example, the sohei
) to do his fighting for him--but is that also not a measure of great leadership? Oda was assassinated by Akechi Mitsudhide, one of his retainers, plunging the country into another round of wars which lasted a generation, from which Tokugawa Ieyasu emerged victorious.