Sakakibara Yasumasa is a relatively lesser-known figure among the Tokugawa’s Four Heavenly Kings, overshadowed by Honda Tadakatsu and Ii Naomasa. Nonetheless, Yasumasa’s deep connection with the Tokugawa family, as his previous generations served Ieyasu’s father, Matsudaira Hirotada, sets him apart from Naomasa and Tadakatsu.
Yasumasa, born in 1548, shares a similar age with Tadakatsu and is 6 years younger than Ieyasu. Their first encounter took place when Yasumasa was only 13 years old and named Koheira. At the time, Ieyasu, after hearing that Imagawa Yoshimoto had been defeated by Nobunaga at Okehazama, moved to Daijuji Temple on the outskirts of Okazaki Castle to watch the situation. The young Koheira, learning calligraphy and reading from a monk at this temple, was then called upon to become one of the 19-years-old Ieyasu’s aides. Eventually, Ieyasu formed an alliance with Oda Nobunaga after severing ties with the Imagawa clan.
Koheira’s first battle occurred at the age of sixteen during the Ikko-Ikki uprising in Mikawa in 1563. Taking advantage of the situation, Sakai Tadanao, a senior retainer of the Matsudaira clan and the lord of Ueno Castle, rebelled against Ieyasu. Tadakatsu and Koheira joined the forces attacking Ueno Castle. Faced with the Ikko-Ikki rebels and the Sakai forces chanting “Namu Amida Butsu”, Koheira’s valiant words saying “I will vanquish every enemy, even if I become an enemy of the Buddha himself!” inspired the Tokugawa forces to finally repel the enemies.
In recognition of this achievement, Koheira received the character “Yasu” (康) from Ieyasu and changed his name to Yasumasa. After the suppression of the Ikko-Ikki, Ieyasu’s battles gradually expanded. It is said that Yasumasa always took the forefront. When Yasumasa was twenty-one years old, his name appeared among the “most trusted two subordinates” in a letter from Ieyasu. Following this, Yasumasa continued to fight valiantly in battles such as the Siege of Kakegawa, the Battle of Anegawa, and the Battle of Mikatagahara. In 1584, during the battles of Komaki and Nagakute, he not only displayed his martial valor but also wrote a lengthy proclamation stating, “Hideyoshi is a traitor who draws his bow against Nobunaga’s family. It is crucial to punish this wicked and unjust man”, distributing it not only to allies but also to enemies in Hideyoshi’s camp, greatly dampening their morale and enraging Hideyoshi.
Ieyasu regarded Yasumasa as the person with the highest character and proudly proclaimed, “Yasumasa is the best among my subordinates”.
After the Battle of Odawara, Yasumasa was granted the territory of 100,000 koku in Tatebayashi, Kōzuke Province. During the Battle of Sekigahara, he accompanied the tardy Hidetada to the decisive battlefield. After the battle, when Ieyasu reprimanded Hidetada for his tardiness, Yasumasa argued in Hidetada’s defense without hesitation, engaging in a debate that ultimately calmed Ieyasu’s anger with his eloquence.
Yasumasa died of illness at the Tatebayashi Castle in 1606 at the age of 59.
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