Yoshiaki, a loyal vassal of the Oda clan, first distinguished himself as a talented warrior during the Battle of Shizugatake in 1583. For his bravery and outstanding military achievements, he was included in the famous group known as the “Seven Spears of Shizugatake” — an elite band of samurai celebrated for their exceptional courage in that battle. Later, Yoshiaki became one of Toyotomi Hideyoshi’s naval admirals and took an active part in his subsequent military campaigns. He commanded warships during the expeditions to Kyushu and the siege of Odawara, demonstrating not only valor but also exceptional leadership and strategic skill. For his loyal service and effective command, Yoshiaki was granted an estate in Matsuzaki with an annual income of 100,000 koku of rice — a symbol of significant rank and prosperity.
During the first and second Korean campaigns, Yoshiaki continued to serve under Hideyoshi’s banner, participating in several naval battles along the southern coast of the Korean Peninsula. His fleet played a vital role in securing Japanese dominance at sea, and Yoshiaki earned a reputation as an experienced naval commander capable of leading effectively under the harsh conditions of long-distance warfare.
After the death of Toyotomi Hideyoshi, Kato Yoshiaki entered the service of Tokugawa Ieyasu, proving himself a wise and farsighted statesman who understood where the future of Japan lay. In 1600, he fought on the side of Tokugawa during the decisive Sekigahara campaign, which shaped the destiny of Japan for generations to come. During the Battle of Sekigahara, Yoshiaki commanded a 3,000-man unit in the vanguard of the Eastern Army and engaged fiercely with the forces led by Shima Sakon. His troops showed remarkable endurance and discipline, contributing significantly to the ultimate victory of the Tokugawa forces.
For his loyalty and valor, Tokugawa Ieyasu generously rewarded Yoshiaki by granting him vast lands in Iyo Province on the island of Shikoku (modern-day Ehime Prefecture), with his annual income increased to 200,000 koku of rice. This reward reflected Tokugawa’s deep trust and recognition of Kato Yoshiaki as one of the most distinguished military commanders of his era.
As a symbol of his power and the dawn of a new age, Kato Yoshiaki ordered the construction of the magnificent Matsuyama Castle on his new lands, which would become the main seat of his clan. Construction began in 1602 and lasted for twenty-five years, making it one of the grandest architectural projects of its time. Approximately 150,000 stone blocks were used to build its massive walls and towers. Over time, Matsuyama Castle became not only the administrative center of Yoshiaki’s domain but also one of the finest examples of Japanese defensive architecture from the early Edo period — a lasting symbol of strength, wisdom, and devotion to the samurai spirit.
See also
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Yamagata Masakage
Masakage was one of Takeda Shingen’s most loyal and capable commanders. He was included in the famous list of the “Twenty-Four Generals of Takeda Shingen” and also belonged to the inner circle of four especially trusted warlords known as the Shitennō.
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Yagyu Munenori
Yagyū Munenori began his service under Tokugawa Ieyasu while his father, Yagyū Muneyoshi, was still at his side. In 1600, Munenori took part in the decisive Battle of Sekigahara. As early as 1601, he was appointed a kenjutsu instructor to Tokugawa Hidetada, Ieyasu’s son, who later became the second shogun of the Tokugawa clan.
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Yagyu Muneyoshi
A samurai from Yamato Province, he was born into a family that had been defeated in its struggle against the Tsutsui clan. Muneyoshi first took part in battle at the age of sixteen. Due to circumstances beyond his control, he was forced to enter the service of the Tsutsui house and later served Miyoshi Tōkei. He subsequently came under the command of Matsunaga Hisahide and in time became a vassal first of Oda and later of Toyotomi.
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Endo Naozune
Naozune served under Azai Nagamasa and was one of the clan’s leading vassals, renowned for his bravery and determination. He accompanied Nagamasa during his first meeting with Oda Nobunaga and at that time asked for permission to kill Nobunaga, fearing him as an extremely dangerous man; however, Nagamasa did not grant this request.
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Hosokawa Sumimoto
Sumimoto came from the Hosokawa clan: he was the biological son of Hosokawa Yoshiharu and at the same time the adopted son of Hosokawa Masamoto, the heir of Hosokawa Katsumoto, one of the principal instigators of the Ōnin War. Masamoto was homosexual, never married, and had no children of his own. At first he adopted Sumiyuki, a scion of the aristocratic Kujō family, but this choice provoked dissatisfaction and sharp criticism from the senior vassals of the Hosokawa house. As a result, Masamoto changed his decision and proclaimed Sumimoto as his heir, a representative of a collateral branch of the Hosokawa clan that had long been based in Awa Province on the island of Shikoku. Almost immediately after this, the boy became entangled in a complex and bitter web of political intrigue.
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Honda Masanobu
Masanobu initially belonged to the retinue of Tokugawa Ieyasu, but later entered the service of Sakai Shōgen, a daimyo and priest from Ueno. This shift automatically made him an enemy of Ieyasu, who was engaged in conflict with the Ikkō-ikki movement in Mikawa Province. After the Ikkō-ikki were defeated in 1564, Masanobu was forced to flee, but in time he returned and once again entered Ieyasu’s service. He did not gain fame as a military commander due to a wound sustained in his youth; nevertheless, over the following fifty years he consistently remained loyal to Ieyasu.
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Honda Masazumi
Masazumi was the eldest son of Honda Masanobu. From a young age, he served Tokugawa Ieyasu alongside his father, taking part in the affairs of the Tokugawa house and gradually gaining experience in both military and administrative matters. At the decisive Battle of Sekigahara in 1600, Masazumi was part of the core Tokugawa forces, a clear sign of the high level of trust Ieyasu placed in him. After the campaign ended, he was given a highly sensitive assignment—serving in the guard of the defeated Ishida Mitsunari, one of Tokugawa’s principal enemies—an obligation that required exceptional reliability and caution.
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Hojo Shigetoki
Hōjō Shigetoki, the third son of Hōjō Yoshitoki, was still very young—only five years old—when his grandfather Tokimasa became the first member of the Hōjō clan to assume the position of shogunal regent.
