Shima Kiyooki (島清興)
Kiyooki SHIMA was a busho (military commander) and vassal (strategist) of Mitsunari ISHIDA who lived during the Azuchi-momoyama period. He was widely known by the common name of 'Sakon SHIMA', and he was respected so much that it was said that 'Jibusho (Mitsunari) had two valuable things: Sakon SHIMA and Sawayama-jo castle' (his name is noted as 'Sakon (SHIMA)' in this section unless otherwise specified). It is commonly said that his real name was Katsutake, but Kiyooki is correct according to archives. His daughter was the second wife of Toshiyoshi YAGYU, and Yoshikane YAGYU who was famous as a kengo (a great swordsman) was his grandchild.
There is a theory stating that he was born in Tsushima Province, but it is now clear that he was born in Yamato Province (recently there has also been another theory that 'Sakon SHIMA' was a name of the Shima clan who served the Tsutsui clan and that there was another person named 'Sakon SHIMA' before Kiyooki).
Hatakeyama, Tsutsui, and Toyotomi Clan Periods
Kiyooki SHIMA was born in a family of local lords of Yamato Province. The Shima clan was considered to be a resident landholder around present-day Heguri-cho, Ikoma County, Nara Prefecture, and Kiyooki SHIMA was initially a shugo (military governor) of the adjacent province of Kawachi, and served the Hatakeyama clan who wielded their influence in Yamato Province as well. He took part in the Battle of Kyoko-ji Temple in which Takamasa HATAKEYAMA fought Nagayoshi MIYOSHI, but Takamasa HATAKEYAMA was defeated and Kiyooki SHIMA fled. Since he fought under command of Junsei TSUTSUI during this time, he became one of the local lords belonging to the Tsutsui clan after the fall of the Hatakeyama clan, gradually distinguished himself, and as a samurai taisho (a warrior who gives battle orders and maneuvers troops), he supported Junkei TSUTSUI who succeeded Junsei at the age of no older than two. He continued to fight an intense battle against Hisahide MATSUNAGA (Battle of Tsutsui-jo Castle, Battle of Daibutsu-den Hall [the Great Buddha hall] of Todai-ji Temple) for control of Yamato Province and continued to support Junkei even during a crisis in which the castle of the Tsutsui clan was temporarily lost. He and Shigenobu MATSUKURA (Ukon) were called the two wings (Ukon and Sakon) of the Tsutsui clan due to their conspicuous service. He defeated Hisahide MATSUNAGA, got over a life-or-death crisis at "the Honnoji Incident", and helped the Tsutsui clan to unify Yamato Province, but soon after that, his load, Junkei, with whom he shared joys and sorrows, succumbed to disease. He had a disagreement with the nephew of Junkei, Sadatsugu TSUTSUI, who succeeded Junkei, and left the Tsutsui clan. He went on to serve Hidenaga TOYOTOMI, Hideyasu TOYOTOMI and others, but after the fall of the Yamato Toyotomi family, he became a ronin (masterless samurai) and led a secluded life in Omi Province.
Ishida Clan Period
Mitsunari ISHIDA who became the local lord of Omi asked Sakon to serve him. Sakon, who had declined many requests until then, also declined that of Ishida but he finally accepted after his earnest persuasion and was employed with a horoku (stipend) of 200,000 koku. This was treatment unprecedented at the time because a half of Mitsunari's horoku of 400,000 koku was given to Sakon.
There is a reliable theory which states that Sakon SHIMA served Mitsunari ISHIDA after he had become lord of Sawayama, a 190,000 koku fief. Even so, it was still an unprecedented promotion. Because it is stated in "Tamonin nikki" (Diary compiled at Tamonin Temple) that the wife of Sakon was 'now in Goshu Saho no shiro (Sawayama-jo Castle)' in May, 1592, it is thought that he served Mitsunari at that time.
During war in Korea, Sakon SHIMA joined Mitsunari and traveled to Korea where he assisted with military affairs. When Hideyoshi TOYOTOMI died in 1598 and Ieyasu TOKUGAWA began to exert his power, Sakon considered it dangerous, and proposed a plan to assassinate Ieyasu to Mitsunari, but Mitsunari considered it unjustifiable and did not accept it. There was a famous plot in which it was planned that Masaie NAGATSUKA of Minakuchi-okayama-jo Castle in Omi Province would welcome Ieyasu who had traveled east to conquest Aizu before Sakon and others sneaked into the castle and killed him. Masaie reluctantly agreed to Sakon's plan, and succeeded in making a promise with Ieyasu but he received a report from kancho (spy) during the previous night and broke the promise, causing the Sakon's plan to fail.
Battle of Sekigahara
To encourage the soldiers of the 'western' army, who were frightened by a report that Ieyasu arrived at Akasaka, Mino Province, though he was considered not to be able to move from Edo in fear of betrayal of Kagekatsu UESUGI of Aizu and Masamune DATE in the north region, Sakon led a squad of 500 soldiers to fight against the 'eastern' army of Kazuhide NAKAMURA and Toyouji ARIMA (Battle of Kuise-gawa River) in the evening before the Battle of Sekigahara in 1600, and his squad and the squad of Takenori AKASHI (vassal of Hideie UKITA) won a complete victory. However, the night attack proposed by Sakon, Yoshihiro SHIMAZU and Yukinaga KONISHI at that night was not approved by Mitsunari (there is also a theory that states that no night attack was proposed. The plan of the night attack was written in the 'History of Japanese Warfare (Old Japanese Military staff headquarters)'. In the final battle of the Battle of Sekigahara, the 'western' army was the first to gain an advantage and Sakon took the lead and fought bravely, but he was shot from the flank by Nagamasa KURODA's firearm unit and made a temporary retreat (it is also said that he died at this time). After noon, the 'western' army collapsed completely due to betrayal by Hideaki KOBAYAKAWA. Sakon prepared to die in battle and once again departed for the front where he attacked the armies of Yoshimasa TANAKA, Nagamasa KURODA and others in assault in which it is said that he fought bravely but was shot dead by the enemy. In the early Edo period, busho (Japanese military commanders) who fought in Sekigahara and witnessed Shima told young samurai about the clothes of Shima, but their memories of his measurements, jinbaori (sleeveless campaign jacket worn over armor) and armor differed, and it is said that this was because their memories were hazy due to the horrible appearance of Shima.