Lifespan: Tenbun 22 (1553) (?) to Kanei 20 (1643) (?)
Title: Governor of Yamashiro, Governor of Harima, Chief of the Weaving Office
Clan: Hachijō-Uesugi → Jōjō-Uesugi
Lord: Uesugi Kenshin → Uesugi Kagekatsu → Toyotomi Hideyoshi → Toyotomi Hideyori → Tokugawa Ieyasu → Tokugawa Hidetada
Father: Uesugi Sadazane
Adoptive Father: Uesugi Yorifusa or Jōjō Sadanori
Wife: Daughter of Nagao Masakage
Adopted Children: Hatakeyama Yoshiharu
Jōjō Masashige served as a bushō from the Sengoku to early Edo periods. He was a retainer of the Uesugl clan and the head of the Jōjō-Uesugi family. Masashige served as the lord of Jōjō Castle in Echigo Province. According to one theory, Masashige was the underling of Uesugi Sadazane, the military governor of Echigo and a member of the Jōjō-Uesugi family.
Masashige was born as the son of Uesugi Sadazane of the Hachijō-Uesugi family.
The Jōjō-Uesugi family opposed Nagao Tamekage and collapsed. In 1571, however, it appears that Masashige inherited the headship of the Jōjō-Uesugi family which had been discontinued in the era of Tamekage’s son, Uesugi Kenshin. By the early years of the Tenshō era (1573 to 1593), he entered the priesthood and adopted the name of 宜順.
Masashige served Kenshin and engaged in battles across Kōzuke and Etchū provinces. According to a historical account of military service in the Uesugi family dating from 1575, Masashige was responsible for the military service of 96 individuals and was in the fourth rank among members of the Uesugi family. In 1577, in connection with the assault of Nanao Castle, the base of the Hatakeyama clan serving as the military governors of Noto, upon orders of Kenshin, Masashige adopted as his heir an orphan of the Hatakeyama clan (Hatakeyama Yoshitsugu (later known as Yoshiharu).
After the death of Kenshin, during the ensuing succession struggle known as the Otate Conflict, Masashige allied with Uesugi Kagekatsu and, after the conflict, continued to support Kagekatsu in the capacity of a senior retainer. In 1581, Kawada Nagachika of Matsukura Castle died whereupon Masashige entered the castle as his successor. In 1584, after sending hostages to Hashiba Hideyoshi, Kagekatsu did not have a natural son at the time so Masashige sent his grandson, Hatakeyama Yoshizane (Yoshiharu’s son), to be adopted by Kagekatsu and he was exempted from military service.
That same year, following the downfall of Yamaura Kagekuni of Kaizu Castle (later known as Matsushiro Castle) in Shinano, Masashige entered Kaizu Castle as his successor but, in 1585, he was replaced by Suda Mitsuchika leading to conflict with Kagekatsu. In 1586, Masashige absconded from the Uesugi family and turned to Toyotomi Hideyoshi. He was granted a fief of 500 koku in Suda and Hōya in the Takayasu District of Kawachi Province. Historical accounts thereafter refer to his adopted son, Yoshiharu, so it is presumed that Masashige died around this time. His reasons for leaving the Uesugi are understood to have been conflicts with Kagekatsu regarding the governance of Shinano, among other issues. Other theories include slander by Naoe Kanetsugu, a rising associate of Kagekatsu, or a close relationship with Shibata Shigeie who, at the time, was rebelling against the Uesugi clan.
According to other theories, Masashige resided at Nagoya Castle in Hizen Province during the Bunroku-Keichō Campaign. In 1600, he joined the Eastern Army at the Battle of Sekigahara. In 1614, at the Winter Campaign of the Siege of Ōsaka, Masashige departed the castle along with Katagiri Katsumoto who was suspected of colluding with the Tokugawa. In 1615, at the Summer Campaign of the Siege of Ōsaka, he joined the Tokugawa forces. After the war, he served the Edo bakufu and died in 1643. Later, he settled with the Uesugi clan and Yoshiharu’s second son, Uesugi Nagakazu, served as a hatamoto, or direct retainer of the bakufu, in the role of a kōke responsible for arranging ceremonies. His stipend exceeded that of hatamoto from the Takuma-Uesugi and the Fukuya-Uesugi families.