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In 1585 a quarrel between his father Masayuki and [[Hojo Ujimasa|Hôjô Ujimasa]] over [[Numata castle]] came to a head, and [[Tokugawa Ieyasu]] made plans to attack the Sanada castle of [[Ueda castle|Ueda]]. In response, Masayuki made overtures to [[Uesugi Kagekatsu]] of [[Echigo province]] and sent Yukimura as a hostage, where he was placed under the watchful eye of Uesugi general [[Suda Mitsuchika]]. A letter of from him dated 8/29 mentions Yukimura's arrival and says that in return, a force had been sent to aid the Sanada in their struggle against the Tokugawa. Ieyasu's [[First Siege of Ueda|attack on Ueda Castle]] ended in utter failure.  Towards the end of the year Masayuki made overtures to [[Toyotomi Hideyoshi]], guaranteeing a quick end to the quarrel with Ieyasu. Perhaps one result of submitting to Hideyoshi was that Yukimura was able to leave the Uesugi, who had also pledged allegiance to Hideyoshi.
 
In 1585 a quarrel between his father Masayuki and [[Hojo Ujimasa|Hôjô Ujimasa]] over [[Numata castle]] came to a head, and [[Tokugawa Ieyasu]] made plans to attack the Sanada castle of [[Ueda castle|Ueda]]. In response, Masayuki made overtures to [[Uesugi Kagekatsu]] of [[Echigo province]] and sent Yukimura as a hostage, where he was placed under the watchful eye of Uesugi general [[Suda Mitsuchika]]. A letter of from him dated 8/29 mentions Yukimura's arrival and says that in return, a force had been sent to aid the Sanada in their struggle against the Tokugawa. Ieyasu's [[First Siege of Ueda|attack on Ueda Castle]] ended in utter failure.  Towards the end of the year Masayuki made overtures to [[Toyotomi Hideyoshi]], guaranteeing a quick end to the quarrel with Ieyasu. Perhaps one result of submitting to Hideyoshi was that Yukimura was able to leave the Uesugi, who had also pledged allegiance to Hideyoshi.
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Yukimura served under Hideyoshi and married the daughter of a senior Toyotomi retainer [[Otani Yoshitsugu |Ôtani Yoshitsugu]]. In 1594 on the orders of Hideyoshi, Yukimura, along with his father and brother, played leading roles in the construction of [[Fushimi castle]].
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Yukimura served under Hideyoshi and married the daughter of a senior Toyotomi retainer [[Otani Yoshitsugu |Ôtani Yoshitsugu]]. In [[1594]] on the orders of Hideyoshi, Yukimura, along with his father and older brother, was ordered to provide men for the construction of [[Fushimi castle]]. Yukimura was a younger son, and he had still younger brothers, but the fact that he was named along with Nobuyuki shows his importance in the clan.
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In 1600, in the prelude to the [[Battle of Sekigahara]], the Sanada clan, now allies of the Tokugawa, began their advance against the Uesugi (who had relocated to Aizu). However, on 7/17 [[Ishida Mitsunari]] orchestrated an indictment against Ieyasu on 13 charges that was endorsed by three of the bugyô regents ruling on behalf of the Hideyoshi’s heir, the child [[Toyotomi Hideyori]]. With Ieyasu effectively named an enemy of the state, Mitsunari issued an invitation to the Sanada to rethink their current support for Ieyasu and join the Western, anti-Tokugawa coalition. Faced with a complex dilemma on the eve of an all or nothing struggle between Ieyasu and Mitsunari’s coalition, Masayuki complied with Mitsunari’s wishes and immediately withdrew his forces from the field and returned to Ueda, taking Yukimura with him. He left his older son Nobuyuki with Ieyasu, presumably to make sure that the clan would survive—no matter which side, East or West, won.  This was not an unusual move in Japan.  (Nobuyuki's father-in-law was a close retainer of Ieyasu's and Masayuki may have guessed or known that Yukimura's father-in-law Ôtani Yoshitsugu would support Mitsunari.)  Once word of Masayuki’s change of allegiance reached Ieyasu, he promptly told Nobuyuki he would be given his father's land once the Western coalition was successfully defeated.
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In 1600, in the prelude to the [[Battle of Sekigahara]], the Sanada clan, now allies of the Tokugawa, began their advance against the Uesugi (who had relocated to Aizu). However, on 7/17 [[Ishida Mitsunari]] orchestrated an indictment against Ieyasu on 13 charges that was endorsed by three of the bugyô regents ruling on behalf of the Hideyoshi’s heir, the child [[Toyotomi Hideyori]]. With Ieyasu effectively named an enemy of the state, Mitsunari issued an invitation to the Sanada to rethink their current support for Ieyasu and join the Western, anti-Tokugawa coalition. Faced with a complex dilemma on the eve of an all or nothing struggle between Ieyasu and Mitsunari’s coalition, Masayuki complied with Mitsunari’s wishes and immediately withdrew his forces from the field and returned to Ueda, taking Yukimura with him. He left his older son Nobuyuki with Ieyasu, presumably to make sure that the clan would survive—no matter which side, East or West, won.  This was not an unusual move in Japan.  (Nobuyuki's father-in-law was a close retainer of Ieyasu's and Masayuki may have guessed or known that Yukimura's father-in-law Ôtani Yoshitsugu would support Mitsunari.)  When word of Masayuki’s change of allegiance reached Ieyasu, he promptly told Nobuyuki he would be given his father's land (which was of course contingent on the defeat of the Western coalition).
    
Now with the Masayuki and Yukimura’s position clear, Ieyasu's son [[Tokugawa Hidetada|Hidetada]] attacked the father and son at Ueda Castle ([[Second Siege of Ueda]]) on his way to Sekigahara to support his father. The siege at Ueda lasted only eight days and ended in failure for Hidetada, whose 38,000-strong army arrived too late to take part in the fighting at Sekigahara and nearly jeopardized his father’s victory.  
 
Now with the Masayuki and Yukimura’s position clear, Ieyasu's son [[Tokugawa Hidetada|Hidetada]] attacked the father and son at Ueda Castle ([[Second Siege of Ueda]]) on his way to Sekigahara to support his father. The siege at Ueda lasted only eight days and ended in failure for Hidetada, whose 38,000-strong army arrived too late to take part in the fighting at Sekigahara and nearly jeopardized his father’s victory.  
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