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A noted administrator, Yoshimoto carried out a series of land surveys and transformed his capital of Sumpu into a cultural center. Yoshimoto himself was said to have had the habit of shaving his eyebrows and blackening his teeth in the manner of a Kyoto noble; one of his wives was of noble blood and is said to have assisted him in this area. Militarily, Yoshimoto worked towards consolidating the Imagawa domain and was greatly aided by his uncle, the monk-general [[Sessai Choro]] (aka. Taigen Sessai; d.[[1557]]). He secured Imagawa influence over Tôtomi and made a series of political maneuvers that led to the submission of the Matsudaira in [[1548]] and the acquisition of the future [[Tokugawa Ieyasu]] as a hostage.  

A noted administrator, Yoshimoto carried out a series of land surveys and transformed his capital of Sumpu into a cultural center. Yoshimoto himself was said to have had the habit of shaving his eyebrows and blackening his teeth in the manner of a Kyoto noble; one of his wives was of noble blood and is said to have assisted him in this area. Militarily, Yoshimoto worked towards consolidating the Imagawa domain and was greatly aided by his uncle, the monk-general [[Sessai Choro]] (aka. Taigen Sessai; d.[[1557]]). He secured Imagawa influence over Tôtomi and made a series of political maneuvers that led to the submission of the Matsudaira in [[1548]] and the acquisition of the future [[Tokugawa Ieyasu]] as a hostage.  

In his westward expansion, Yoshimoto came into conflict with the [[Oda clan|Oda]] of Mikawa, and fought with them on a number of occasions, including the [[Battle of Azukizaka]] in [[1542]] - which Yoshimoto lost. Yoshimoto was afterwards content to leave the fighting to Sessai, though he was not with military skill himself. Yoshimoto's greatest gifts, however, lay within the political realm, and in [[1545]] he engineered a three way union between the [[Takeda clan|Takeda]], Hôjô, and Imagawa. Yoshimoto was clearly respected by his peers, and was often in the position of mediator - such as when [[Hojo Ujiyasu|Hôjô Ujiyasu]] requested he ask [[Takeda Shingen]] not to attack Kozuke as the Hôjô were preparing to do so.  

In his westward expansion, Yoshimoto came into conflict with the [[Oda clan|Oda]] of Mikawa, and fought with them on a number of occasions, including the [[Battle of Azukizaka]] in [[1542]] - which Yoshimoto lost. Yoshimoto was afterwards content to leave the fighting to Sessai, though he was not without military skill himself. Yoshimoto's greatest gifts, however, lay within the political realm, and in [[1545]] he engineered a [[Hojo-Takeda-Imagawa Alliance|three way union]] between the [[Takeda clan|Takeda]], Hôjô, and Imagawa. Yoshimoto was clearly respected by his peers, and was often in the position of mediator - such as when [[Hojo Ujiyasu|Hôjô Ujiyasu]] requested he ask [[Takeda Shingen]] not to attack Kozuke as the Hôjô were preparing to do so.  

By the close of the 1550's, Yoshimoto enjoyed a strong position and began to consider marching on Kyoto. Sessai had died in [[1557]], but the Imagawa had been able to call on the talents of the young Matsudaira Motoyasu (Tokugawa Ieyasu) to check the activities of [[Oda Nobunaga]], and by [[1560]] Yoshimoto felt confident enough to call his entire army to arms. He mustered somewhere between 15,000 and 20,000 men from Suruga and Mikawa and in June 1560 departed for Kyoto. Two of Oda's forts (Marume and Terabe) were reduced, and a confident Yoshimoto called for his men to rest in the Dengakuhazama (near Okehazama) where he viewed the heads taken thus far and enjoyed a musical performance. Unbeknownst to the Imagawa, Oda Nobunaga had resolved to take the offensive, and had managed to creep right up on Yoshimoto's encampment. Following a terrific thunderstorm, Oda's men attacked, and such was the suddenness and violence of their charge Yoshimoto initially assumed a fight had broken out among his men. Amidst the growing confusion, Yoshimoto was set upon by a number of Oda warriors. He managed to cripple one with a blow of his sword, but was struck down by a certain [[Mori Shinnosuke]]. When word of his death spread, the Imagawa army fled precipitously, signaling not only the end of Yoshimoto but also an eventual end to the Imagawa. Indeed, his successor Ujizane ([[1538]]-[[1614]]) would suffer the loss of his lands to the Tokugawa and Takeda by [[1569]], and in the end retired to Kyoto, providing a certain element of irony to the demise of the once-proud Imagawa clan.  

By the close of the 1550's, Yoshimoto enjoyed a strong position and began to consider marching on Kyoto. Sessai had died in [[1557]], but the Imagawa had been able to call on the talents of the young Matsudaira Motoyasu (Tokugawa Ieyasu) to check the activities of [[Oda Nobunaga]], and by [[1560]] Yoshimoto felt confident enough to call his entire army to arms. He mustered somewhere between 15,000 and 20,000 men from Suruga and Mikawa and in June 1560 departed for Kyoto. Two of Oda's forts (Marume and Terabe) were reduced, and a confident Yoshimoto called for his men to rest in the Dengakuhazama (near Okehazama) where he viewed the heads taken thus far and enjoyed a musical performance. Unbeknownst to the Imagawa, Oda Nobunaga had resolved to take the offensive, and had managed to creep right up on Yoshimoto's encampment. Following a terrific thunderstorm, Oda's men attacked, and such was the suddenness and violence of their charge Yoshimoto initially assumed a fight had broken out among his men. Amidst the growing confusion, Yoshimoto was set upon by a number of Oda warriors. He managed to cripple one with a blow of his sword, but was struck down by a certain [[Mori Shinnosuke]]. When word of his death spread, the Imagawa army fled precipitously, signaling not only the end of Yoshimoto but also an eventual end to the Imagawa. Indeed, his successor Ujizane ([[1538]]-[[1614]]) would suffer the loss of his lands to the Tokugawa and Takeda by [[1569]], and in the end retired to Kyoto, providing a certain element of irony to the demise of the once-proud Imagawa clan.