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In [[1582]] Kagekatsu led an army into Etchu and was defeated by Oda forces at the [[Battle of Tenjinyama]]. He hastily returned to [[Echigo province|Echigo]] when he learned that Oda general [[Mori Nagayoshi]] had raided Echigo in his absence. When [[Uozu castle]] in Etchu fell to the Oda, in the course of which a number of important Uesugi retainers were killed, Kagekatsu's fortunes appeared bleak. The Uesugi were given a reprieve with the death of Nobunaga shortly afterwards. Kagekatsu made friendly overtures to [[Toyotomi Hideyoshi|Hashiba (Toyotomi) Hideyoshi]], and attacked Shibata Kasuie's northern outposts during the [[Shizugatake Campaign]] ([[1583]]). He was therefore confirmed in his Echigo fief (worth 550,000 koku) and went on to support Hideyoshi during the [[Komaki Campaign]] ([[1584]]), in which he played a limited role by launching a foray into [[Shinano province|Shinano]]. He attacked Hojo forts in [[Kozuke province|Kozuke]] during the [[1590]] [[Odawara Campaign]] and in [[1598]] was transferred to Aizu (worth almost 1,000,000 koku), an area of western Mutsu controlled by the Ashina prior to [[1589]].  

In [[1582]] Kagekatsu led an army into Etchu and was defeated by Oda forces at the [[Battle of Tenjinyama]]. He hastily returned to [[Echigo province|Echigo]] when he learned that Oda general [[Mori Nagayoshi]] had raided Echigo in his absence. When [[Uozu castle]] in Etchu fell to the Oda, in the course of which a number of important Uesugi retainers were killed, Kagekatsu's fortunes appeared bleak. The Uesugi were given a reprieve with the death of Nobunaga shortly afterwards. Kagekatsu made friendly overtures to [[Toyotomi Hideyoshi|Hashiba (Toyotomi) Hideyoshi]], and attacked Shibata Kasuie's northern outposts during the [[Shizugatake Campaign]] ([[1583]]). He was therefore confirmed in his Echigo fief (worth 550,000 koku) and went on to support Hideyoshi during the [[Komaki Campaign]] ([[1584]]), in which he played a limited role by launching a foray into [[Shinano province|Shinano]]. He attacked Hojo forts in [[Kozuke province|Kozuke]] during the [[1590]] [[Odawara Campaign]] and in [[1598]] was transferred to Aizu (worth almost 1,000,000 koku), an area of western Mutsu controlled by the Ashina prior to [[1589]].  

That same year he was named one of Five Regents ([[Go-Tairo]]) and following Hideyoshi's death grew hostile to [[Tokugawa Ieyasu]]. In [[1600]] Kagekatsu began preparations for war, and in effect opened the [[Sekigahara Campaign]]. His army, which [[Ishida Mitsunari]] had hoped would tie down Tokugawa Ieyasu himself, clashed with the forces of [[Date Masamune]] and [[Mogami Yoshiakira]] and gained little in the battles conducted in and around Aizu. After the Tokugawa victory at the [[Battle of Sekigahara]], Ieyasu transferred the Uesugi fief to Yonezawa and reduced their income to around 300,000 koku.  

That same year he was named one of Five Regents ([[Go-Tairo]]) and following Hideyoshi's death grew hostile to [[Tokugawa Ieyasu]]. In [[1600]] Kagekatsu began preparations for war, and in effect opened the [[Sekigahara Campaign]]. His army, which [[Ishida Mitsunari]] had hoped would tie down Tokugawa Ieyasu himself, clashed with the forces of [[Date Masamune]] and [[Mogami Yoshiakira]] and gained little in the battles conducted in and around Aizu. After the Tokugawa victory at the [[Battle of Sekigahara]], Ieyasu transferred the Uesugi from their 1.2 million ''[[koku]]'' fief to [[Yonezawa domain]] (300,000 ''koku''). While this left the Uesugi still one of the wealthiest clans in the realm, despite their prominent place in opposition to Ieyasu, [[Morgan Pitelka]] argues that it was precisely out of respect for that prominence - i.e., for the Uesugi's status, power, reputation - that they deserved, perhaps even were entitled, to remain quite prominent; Pitelka emphasizes, too, that the drop by some 900,000 ''koku'' was still a massive loss, a heavy blow to the Uesugi, appropriate given their opposition and defeat, even if it did leave them still among the most wealthy.<ref>Morgan Pitelka, ''Spectacular Accumulation'', University of Hawaii Press (2016), 83.</ref>

Kagekatsu was able to redeem himself somewhat by taking part in the [[Osaka castle]] campaigns. At the [[Battle of Shigeno]] ([[1614]]) Kagekatsu led 5,000 men into action against the Osaka defenders and distinguished himself by refusing an offer by Ieyasu to retire for rest. Kagekatsu, who died at Yonezawa in [[1623]], was remembered as a dour, humorless man. Although considered a capable enough general, his record was clearly an uneven one.  

Kagekatsu was able to redeem himself somewhat by taking part in the [[Osaka castle]] campaigns. At the [[Battle of Shigeno]] ([[1614]]) Kagekatsu led 5,000 men into action against the Osaka defenders and distinguished himself by refusing an offer by Ieyasu to retire for rest. Kagekatsu, who died at Yonezawa in [[1623]], was remembered as a dour, humorless man. Although considered a capable enough general, his record was clearly an uneven one.