Lifespan: Eiroku 9 (1566) to 9/22 of Kanei 7 (1630)
Other Names: Heiemon; [Common] Saburō-tarō
Clan: Chimura Heiemon
Lord: Kiso Yoshimasa → Kiso Yoshitoshi → Tokugawa Ieyasu → Tokugawa Hidetada → Tokugawa Yoshinao
Father: Chimura Iemasa
Children: Shigenaga, daughter (wife of Baba Masatsugu)
Chimura Yoshishige served as a bushō during the Azuchi-Momoyama and early Edo periods.
In 1566, Yoshishige was born as the son of Chimura Iemasa. Initially, he served Kiso Yoshimasa. Yoshimasa followed Tokugawa Ieyasu and moved to the Kantō. On 12/12 of Tenshō 18 (1590), Yoshimasa appointed Yoshishige as a deputy official with a fief of 700 koku in Hebizone in Tōka in Shimōsa Province and 66 kanmon in Mihiro. After the demise of Yoshimasa, Yoshishige served Kiso Yoshitoshi, but in 1600, Tokugawa Ieyasu removed Yoshitoshi from his position for misconduct. Yoshishige became a rōnin, or wandering samurai, and was later engaged to serve as a retainer of Ieyasu.
Later in 1600, at the Battle of Sekigahara, Yoshishige affiliated with the Eastern Army led by Ieyasu. Owing to his prior service for the Kiso clan, he leveraged his knowledge of the Nakasendō (one of five major roads emanating from Edo) to serve as a guide. He rallied the Mio, the Hara, and other clans comprising the Kiso group dispersed across the area and, on 8/12, toppled a fortress at Niekawa, garnered control of the Kisodani area held by supporters of the Toyotomi, and assaulted Naegi and Iwamura castles in Mino Province. This is known as the Battle of Kiso and Eastern Mino.
Owing to these contributions, Yoshishige became a kōtai-yoriai, or high-ranking retainer of the Edo bakufu, who maintained a residence in his home province along with the obligation to make regular visits to Edo in service of the bakufu. Yoshishige was based in the village of Kukuri in the Kani District of Mino. In Nagoya, he was provided a residence on the north side of Buhei and, in Edo, in three locations in front of the gate to the Zōjō Temple. Further, he had a fief of 4,600 koku in the Ena, Toki, and Kani districts of Mino. Yoshishige managed 11 villages in the Ina District of Shinano that were in the demesne of the shōgun. He also served as the magistrate for logging on Mount Funagira in the Tenryū River Basin in Shinano and Tōtōmi.
In 1614, during the Winter Campaign of the Siege of Ōsaka, Yoshishige served as a guard at the Tsumago checkpoint and Iida Castle in Shinano. During the Summer Campaign in 1615, he participated in the Battle of Tennōji-Okayama.
After the Siege of Ōsaka, while en route to Edo Castle, Ieyasu stopped by Nagoya Castle, summoned Yoshishige and Yamamura Jinbei Yoshikatsu, and declared that Kiso would be added to the Owari domain. Apart from Kiso, Yoshishige also had landholdings in Inadani (in Shinano) and the northern part of Tōtōmi so it was a difficult proposition to accede exclusively to the Owari domain. On the grounds that the Chimura Heiemon family merely represented the Kiso group, Tokugawa Yoshinao sought for them to become exclusive to the Owari domain so he consulted with his older brother, Tokugawa Hidetada (the second shōgun of the Edo bakufu) to request that Yoshishige be ordered to affiliate with the Owari domain. As a result, in 1619, upon orders of Hidetada, Yoshishige served as a direct retainer of the bakufu to govern the demesne of the shōgun in the Ina District of Shinano in addition to serving the Owari domain as a magistrate for logging on Mount Funagira in Tōtōmi Province. Yoshishige inquired via the rōjū, or council of elders, to the shōgun in regard to the governance of Shinano and Tōtōmi. It was decreed that he continue to do so. Yoshishige requested and was permitted to continue to govern the territory in Shinano and in exchange for relinquishing mountainous areas in Tōtōmi desired to oversee logging in the village of Funagira in Tōtōmi.
The Chimura Heiemon family was affiliated with the Owari domain but, at the same time, held positions in the Edo bakufu so, in fact, served both at the same time.
After the Siege of Ōsaka, he affiliated with the Owari domain while also serving the Edo bakufu. Yoshishige was the first head of the Chimura Heiemon family in the Kiso group (former retainers or members of the Kiso clan of Shinano) of the Owari domain.
He died in 1630 at the age of sixty-five. His son, Chimura Shigenaga, inherited the headship of the Chimura Heiemon family.