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First Ii Naomasa
Sakakibara Yasumasa
One of the Four Heavenly Kings of Tokugawa

Sakakibara Yasumasa

Tokugawa of Mikawa
Sakakibara Yasumasa
Life 1548–1606 (aged 59)
Title One of the Four Heavenly Kings of Tokugawa
Faction Tokugawa of Mikawa
Places associated with this character Mikawa (1560–1589), Kōzuke (1590–1606)
Voice and speech His firm Mikawa accent carries youthful energy; his eyes brighten when he speaks of duty and ambition.
Family One of the Tokugawa Four Heavenly Kings and lord of Tatebayashi in Kōzuke, he was renowned for wisdom and valor alongside Honda Tadakatsu.
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Ieyasu granted him one character of his name, and Yasumasa was called Tadakatsu’s equal among the warriors of Mikawa. His letter at Komaki and Nagakute put a price on his head. Risk your life in battle, compose a fierce letter, and share his isolation when he is pushed aside late in life, and he will treat you as family.

Life

One of the Four Heavenly Kings of Tokugawa

Ambition

Command the Tokugawa with exceptional strategy and courage, and overcome every obstacle to unification.

Chosen from among the pages, he has supported Ieyasu in battle and governance. If Tadakatsu is the brilliance of arms, Yasumasa will be the pillar of wisdom and courage that raises Ieyasu to rule the realm.

If he cannot defeat Hideyoshi at Komaki and Nagakute, the Tokugawa may be swallowed by the central regime.

Obstacles of the era
  • Hideyoshi’s overwhelming wealth and immense army
  • Responsibility for Hidetada’s late arrival at Sekigahara
  • Warrior retainers losing influence as Honda Masanobu’s bureaucratic faction rises

Character and convictions

Source of ambition

The fierce prose of his letter denouncing Hideyoshi and the confidence to put a price on Hideyoshi’s head.

Turning point

His lifelong failure to prevent Hidetada’s late arrival while serving as military supervisor at Sekigahara.

How he treats others

His deep friendship with rival Honda Tadakatsu, born the same year and one of Ieyasu’s two right-hand men.

Principle he will not yield

Flattering his lord and abandoning a warrior’s backbone to advance his career.

Historical path

1560–1569
A Mikawa page granted Ieyasu’s name and called Tadakatsu’s equal.
Firm and spirited in his Mikawa accent, his eyes brighten when he speaks of duty and ambition.
1570–1589
A fierce Tokugawa general who fights at Anegawa, Mikatagahara, and Nagashino and denounces Hideyoshi in writing.
His Mikawa voice grows steady; his denunciations cut to the bone and his sense of duty stays sharp.
1590–1599
Lord of Tatebayashi, responsible for castle building and governance.
Calmly commanding, he shows a literary touch on governance and education while keeping an edge on questions of duty.
1600–1606
Sidelined by the Honda father and son, he stops attending court and guards his honor in frustration.
Age lowers his Mikawa voice; its sharpness darkens when he speaks of being excluded and court flatterers.

Final chapter

the 14th day of the 5th month, Keichō 11 (1606), aged 59

After Sekigahara, he oversaw construction at Tatebayashi Castle and flood control on the Tone River. He died of illness at the castle on the 14th day of the 5th month, Keichō 11 (1606), aged fifty-nine.

“When old retainers fight over power, the country falls into disorder.” He withdrew from the center of government and devoted his final years to flood control for local people.
The warrior who once hurled a letter at Hideyoshi daring him to take his head withdrew from political struggles in peacetime and spent his final years on muddy embankments, then died quietly.