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[[Otomo Sadamune]], the 5th head of the family, sided with [[Ashikaga Takauji]] during the latter’s struggle for power and in [[1336]] joined him in marching on Kyoto. Sadamune was involved in fighting with [[Nitta Yoshisada]] and later that same year lost his son Sadanori in a struggle with [[Yuki Chikamitsu]].

[[Otomo Sadamune]], the 5th head of the family, sided with [[Ashikaga Takauji]] during the latter’s struggle for power and in [[1336]] joined him in marching on Kyoto. Sadamune was involved in fighting with [[Nitta Yoshisada]] and later that same year lost his son Sadanori in a struggle with [[Yuki Chikamitsu]].

Later in the [[Nambuchuko Period]], Sadamune’s great-grandson Chikayo fought against his neighbors the Kikuchi, who supported the Southern Court. As a result of Sadamune’s activities, Otomo influence was extended into [[Chikuzen Province|Chikuzen]], [[Hizen Province|Hizen]], and [[Higo Province|Higo]]. During this period he assisted the [[Chinzei Province|Chinzei]] (Kyushu) Tandai [[Imagawa Sadayo]], but once the fighting was over, he banded with the Ouchi to have Sadayo removed. In [[1396]] Sadamune replaced Sadayo as Kyushu Tandai.

Later in the [[Nambuchuko Period]], Sadamune’s great-grandson Chikayo fought against his neighbors the Kikuchi, who supported the Southern Court. As a result of Sadamune’s activities, Otomo influence was extended into [[Chikuzen Province|Chikuzen]], [[Hizen Province|Hizen]], and [[Higo Province|Higo]]. During this period he assisted the [[Kyushu Tandai|Chinzei (Kyushu) Tandai]] [[Imagawa Sadayo]], but once the fighting was over, he banded with the Ouchi to have Sadayo removed. In [[1396]] Sadamune replaced Sadayo as Kyushu Tandai.

The Otomo weathered the [[Onin War]] ([[1467]]-[[1477]]) and entered the 16th Century in a stronger position than many other old Shugo clans. Tensions with the Ouchi of [[Suo Province|Suo]] and [[Nagato Province|Nagato]] brought a war in [[1501]], and a victory for the Otomo in Buzen at Uma-ga-take. Other feuds with other local clans followed, and at various points over the next five decades the Otomo clashed with the Shoni, Tawara, and Tachibana-the last two eventually becoming Otomo vassals. The Hoshino family of Chikuzen also submitted but later revolted, their bid for independence dragging the current Daimyo, [[Otomo Yoshinori]] (Yoshiaki) into a bitter civil war. In [[1550]] Yoshinori was murdered by one of his own retainers, a certain [[Tsukuni Mimasaka]], and his son Yoshishige became the 21st head of the Otomo. As it was said that Yoshinori had planned to disinherit Yoshishige, rumors circulated that patricide had claimed the old Daimyo. Regardless, Yoshishige proved a capable enough leader, and moved to expand the Otomo’s borders deeper into Kyushu. In [[1551]] Yoshishige fought and defeated the rebellious [[Kikuchi Yoshimune]] of Higo; in [[1557]] he invaded Chikuzen and forced [[Akizuki Kiyotane]] into submission. In September of [[1559]] he led an assault that recaptured [[Moji Castle]], which had been lost to the Mori in [[1558]]. The Mori retook Moji soon afterwards and in October [[1561]] Yoshishige attempted to reclaim this strategic prize with an all-out assault that included a number of cannon-equipped Portuguese warships. The warships were used to credible effect, but Yoshishige’s subsequent attack failed, and Moji remained in Mori hands.  

The Otomo weathered the [[Onin War]] ([[1467]]-[[1477]]) and entered the 16th Century in a stronger position than many other old Shugo clans. Tensions with the Ouchi of [[Suo Province|Suo]] and [[Nagato Province|Nagato]] brought a war in [[1501]], and a victory for the Otomo in Buzen at Uma-ga-take. Other feuds with other local clans followed, and at various points over the next five decades the Otomo clashed with the Shoni, Tawara, and Tachibana-the last two eventually becoming Otomo vassals. The Hoshino family of Chikuzen also submitted but later revolted, their bid for independence dragging the current Daimyo, [[Otomo Yoshinori]] (Yoshiaki) into a bitter civil war. In [[1550]] Yoshinori was murdered by one of his own retainers, a certain [[Tsukuni Mimasaka]], and his son Yoshishige became the 21st head of the Otomo. As it was said that Yoshinori had planned to disinherit Yoshishige, rumors circulated that patricide had claimed the old Daimyo. Regardless, Yoshishige proved a capable enough leader, and moved to expand the Otomo’s borders deeper into Kyushu. In [[1551]] Yoshishige fought and defeated the rebellious [[Kikuchi Yoshimune]] of Higo; in [[1557]] he invaded Chikuzen and forced [[Akizuki Kiyotane]] into submission. In September of [[1559]] he led an assault that recaptured [[Moji Castle]], which had been lost to the Mori in [[1558]]. The Mori retook Moji soon afterwards and in October [[1561]] Yoshishige attempted to reclaim this strategic prize with an all-out assault that included a number of cannon-equipped Portuguese warships. The warships were used to credible effect, but Yoshishige’s subsequent attack failed, and Moji remained in Mori hands.