Date Masamune became head of his family in October 1584. At that time his father's loyal retainers, some who had earlier helped raise Masamune and teach him as a child, pledged loyalty to him as they once did his father. They pledged total obedience, to serve without question, to fight his enemies with all their strength and be victorious.

Over the next years, Masamune's retainers advised and helped expanded his territory through wars with Hatakeyama, Ashina, Nambu, Iwaki, Satake, Shirakawa, Mogami, and Uesugi, making Masamune one of the most powerful Daimyo in Japan and drawing the attention and fear of Hideyoshi, who asked for his hand in uniting Japan. Such achievement could not have been possible without the loyalty of his trusted retainers.

Below is a biography of Some of Date's retainers.

Ishikawa Akimitsu (1550-1622): He was born as the 4th son of Date Harumune (1519-1577) who was the 15th head of the Date family, and was adopted by Ishikawa Harumitsu. He fought against the Date at Hitodori and afterwards joined Masamune. In the battle of Domyoji he followed Masamune's example and took 5 enemy heads.

Izumida Shigemitsu (1529-1596): He joined Masamune at the Battle of Soma (1582) and the attack on Nihinmatsu Castle (1585). At the Battle of Oosaki (1588) he went into battle as a leader of one of Date's divisions, but was defeated and held as hostage. In July 1588 he was released after peace negotiations. He was later sent to join Hideyoshi's forces in the Korean campaign.

Katakura Kagetsuna (1557-1615): He was the chief of the general staff of Date's Corps. He achieved many great deeds in battle, especially at Hitadori Bridge and Suriagehara. He was a foresighted person who helped Masamune to strengthen the Date family. During the Korean expedition he was given a battleship for his deeds by Hideyoshi. However, he was also cold-blooded. In a council of discussing the relief of Yamagata Castle, where Masamune's mother was, he proposed deserting the fortress and leaving her to her fate. Masamune was outraged.

Katakura Shigenaga (1585-1659): He was the son of Kagetsuna and was also known as Kojurou. It was said that he was just like his father in respect to his bravery and cleverness. In the Osaka campaign he led the vanguard of Date's army at Domyoji and defeated Goto Motosugu and Susukida Kanesuke. Afterwards, he became known as "Kojurou the devil." At Tennoji he took 5 enemy heads in battle, however, his father scolded him saying "You should have behaved as a general. It's so stupid of you to fight in person." It was also said that he was so handsome that he was chased after by Hideyoshi's adopted son when he made visits to Osaka Castle.

Shiroishi Munezane (1553-1599): In 1586 he was given land by Masamune and the castle of Shionomatsu. In the Battle of Aizu (1589) he achieved a great deed as co-leader with Date Shigeazne and was given Mizusawa Castle along with more land. He was also involved in the Korean expedition.

Suzuki Motonobu (1555-1620): He worked as the Finance Minister and Director General of the Economic Planning Agency in Sendai-han. He was a competent person in administration, management, and battle. Masamune recognized his value and recruited him. Motonobu expected Masamune to control all Japan and prepared a constitution for "Date Shogunate," however, his dream never came true. On his deathbed he ordered all documents destroyed to avoid Tokugawa suspicion.

Date Shigezane (1568-1646): His father was the 3rd son of Date Tanemune (1488-1565) who was the 14th head of the Date family, and his mother was the daughter of Date Harumune, so he was a pure Date by blood. His bravery was second to none. At Hitadori Bridge his corps played a vital defensive role and he was given Nihonmatsu Castle as a reward. He also served with gallantry at the Battles of Kooriyama (1588), Suriagehara (1589), and Sukagawa.

After returning from the Korean campaign, he rebelled and went to Koya-san secretly in 1595 (probably because he was dissatisfied with the reward he got following the campaign). he was later persuaded to come back in 1600 and Masamune gave him Watari Castle. He also joined battle at Osaka in 1615 where he performed admirably. When he visited Edo Castle in 1638, the Shogun, Iemitsu, gave him clothes in admiration of his bravery.

Tsuda Kageyasu (1564-1638): He played an active part in the Battle of Hitadori Bridge, Suriagehara, and Sanuma, and was given Sanuma Castle for his deeds. During the Korean Campaign he fought with distinction. When Masamune was suspected of treason in the Hidetsugu accident, Tsuda made an appeal to Hideyoshi and got Masamune cleared. For his loyalty he was given control of some of some land.

Hasekura Tsunenaga (1571-1622): He was sent to Europe as a mission in 1613. In January 1615 he got to meet the King in Madrid and was baptized. In September he met the Pope in Rome and was given citizenship. However, he failed to achieve Masamune's purpose for the mission. In 1621 he returned to Japan.

On a side note, there is some difference to the letters sent to the Pope by Ieyasu and Masamune. In Ieyasu's letter he stated "I don't mind if you take advantage of coming to Japan to make a profit but don't spread Christianity." On the other hand, Masamune's letter said "I'll offer my land for a base of your missionary work. Send us as many padres as possible."

Harada Munetoki (1565-1593): He was one of Masamune's Syukurou (fudai). Since the age of 18 he had fought in many battles for the Date cause. he also went to the Korean Campaign in 1592, but got sick. He died in Tsushima while en route home.

Moniwa Nobumoto (1549-1640): He worked as the Chief Cabinet Secretary for the Date family. His father was Moniwa Yoshinao who was killed at Hitadori Bridge by Kubota Jyuro. Kubota was later captured and sent to Nobumoto but he released him saying "It's against bushido to kill a prisoner." afterwards, Kubota became his retainer. During the Korean campaign Nobumoto played an active role in supplying goods in Hizen and Nagoya. Hideyoshi liked him and gave him one of his mistresses named Kounomae (she was said to be a great beauty). When Masamune returned home from the war he grew angry with Nobutomo (perhaps he was jealous?). Nobutomo presented Kounomae to Masamune, and he had a boy and girl with her.

Moniwa Yoshinao (1513-1585): In the Battle of Hitadori Bridge he was given command of one of Masamune's corps and a gold fan. However, he was old and unable to wear his armor, so he wore a yellow cap instead—which made him a target. He was killed by Kobuta Jyuro.

Yashiro Kageyori (1561-1608): Masamune always used him to purge rebellions. When Shigezane rebelled he was ordered to subdue him. He attacked Tsunoda Castle and killed many retainers and the wife and children of Shigezane. In 1607 Kageyori was found guilty of a crime and had his lands and property confiscated.

Rusu Masakage (1549-1607): He was the younger brother of Terumune (1544-1585) the 16th head of the Date family. The Rusu was once a distinguished family but its prosperity had been in decline by the end of the Muromachi period. They survived under the protection of the Date by adopting Date's son as head of their family. Masakage was himself adopted by Rusu Akimune (the 17th head) and went to Takamori Castle in 1567. Since that date he served with distinction in many battles. He was also involved in the Korean Campaign.

Watari Motomune (1530-1594): The Watari family ruled over the provinces of Watari, Igu, and Uta. Since 1190 the lordship of these provinces was passed down from father to son. However, the late ruler, Watari Munetaka, had no child for heir. He later adopted Date Motomune, who was a son of Date Terumune. Motomune assumed complete control of the clan. He continued his support of the Date, providing troops and leadership during their campaigns with the Soma.

Related

Date Rulers
Battle of Hitodori Bridge: 17 November 1585