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Matsunaga Hisahide: Misunderstood Daimyo

Off the back of the Miyoshi Nagayoshi article, another figure who keeps appearing in connection to Miyoshi and the lead up to Nobunaga's accession of the Kinai region is Matsunaga Hisahide. I really debated whether to break this one out or just add a few paragraphs to Miyoshi Nagayoshi's story but it's one of those that needed to be told as more than just a sidebar. His story is too compelling not to do more on it. He was a "dandy" a man of highly refined culture, he was an enforcer and fierce warlord in his own right, and a castle innovator. Lavish palaces, tile roods, stone walls and a main keep are innovations starting with Matsunaga that Oda would later claim.

The Enforcer

(proposed only, outline for longer story, maybe delete when longer is done)

Matsunaga Hisahide (松永久秀, c.1510–1577) was one of the most enigmatic figures of the Sengoku period. From humble origins he rose to become a daimyō, a cultured aesthete, political schemer, fierce warrior, and castle innovator. His castles and cultural accomplishments drew the admiration — and perhaps even the jealousy — of Oda Nobunaga himself. Yet despite these achievements, Hisahide is often vilified as one of the “Three Evil Daimyō” (三悪人), alongside Saitō Dōsan and Ukita Naoie.

Hisahide’s origins remain obscure, but recent research suggests he may have come from the Takatsuki area in modern-day Osaka, near the base of his future Akutagawasan Castle. Records and maps note the site of a “Matsunaga Yashiki,” leading historians to theorize that Hisahide’s family were modest local samurai with ties to this region.

When Miyoshi Nagayoshi (三好長慶, 1522–1564) returned to Settsu and began rebuilding his power base, he recruited promising samurai regardless of pedigree. Among them were Hisahide and his brother Nagayori, who would become key to the Miyoshi regime’s success. Hisahide first appears in the records in Nagayoshi’s service in the late 1530s or early 1540s. Without a castle, domain, or hereditary vassals of his own, he relied entirely on ability and cunning. His earliest assignments involved relaying Nagayoshi’s orders to temples and merchants around the Nishinomiya and Hyōgo ports, where he gained a reputation as an able negotiator and administrator. At the Battle of Eguchi (1549), his skill in combat earned him further distinction, and he was elevated to the rank of senior vassal, on par with members of the Miyoshi family such as Miyoshi Nagayasu.

By the early 1550s, Matsunaga Hisahide had become indispensable to the Miyoshi regime — not only as a battlefield commander but also in diplomacy and domestic governance. In recognition of his growing stature, he was granted Takiyama Castle (滝山城) and broad authority in Settsu Province around 1553. Rising above the port, Takiyama commanded the maritime routes and became Hisahide’s first real power base. He renovated the fortress with advanced defenses such as double horikiri (moat cuts) and early stonework, while also cultivating it as a cultural stage. There, he hosted Nagayoshi for renga (linked-verse poetry), Noh performances, and other refined gatherings that projected the image of a warrior deeply attuned to high culture.

From this base Hisahide emerged as the chief enforcer of the Miyoshi regime. He crushed Ashikaga attempts to retake Kyoto, mediated a succession dispute at Iwashimizu Hachimangū, and maintained uneasy peace with the Rokkaku in Ōmi. At the same time, he worked tirelessly to build his own legacy. His marriage into the imperial family through the sister-in-law of the emperor gave him unprecedented access to court circles, allowing him to act as a vital bridge between the court and the Miyoshi. He deepened his cultural pursuits under prominent scholars and hosted events that showcased his refinement. This carefully crafted image of sophistication elevated his standing within the Miyoshi and lent legitimacy to his growing influence at court.

The Daimyo

Once the capital was secured in 1558 (see Miyoshi Nagayoshi), Miyoshi turned his attention to Yamato. To carry out this complex task he relied on his most trusted general and negotiator, Matsunaga Hisahide. At the time Yamato Province was a patchwork of power: the warrior-monks of Kōfukuji and Tōdaiji dominated the land, the Tsutsui clan held nominal sway, and dozens of kokujin families vied for influence. In 1559 Hisahide marched in with 20,000 Miyoshi troops. The campaign was swift. Many Yamato samurai — including the Ochi, Furuichi, Fukuzumi, and Yagyū clans — resented the Tsutsui and quickly allied with Matsunaga. The main target, Tsutsui Junkei at Tsutsui Castle, was tied to Yasumi Munefusa, whom the Miyoshi were already attacking in Kawachi. Neutralizing Junkei both secured Yamato and denied Yasumi a key ally.

With this victory Hisahide became the first warlord to bring Yamato under the unified control of a single daimyō. He ruled with a careful balance of force and accommodation: forging ties with the wealthy merchants of Nara and Sakai, rewarding local allies, and coopting the military strength of Kōfukuji’s warrior-monks. Under his governance, Nara shifted from a city dominated by temples to one governed by warrior authority — a change made visible in the rising silhouette of Tamon Castle, looming above the great temples.

After the invasion Hisahide fortified Shigisan Castle as his military base. The mountaintop castle high up on the range dividing Yamato and Kawachi allowed him to control both provinces while keeping his commercial networks intact. In 1561 he began work on his true masterpiece: Tamon Castle. While Shigisan was the sword of his military presence, Tamon became the stage for his refined persona, hosting tea ceremonies, poetry, and audiences with nobles.

This division of castles reflected Hisahide’s distinctive style of rule — military strength on one hand, cultured statecraft on the other. One might even see a parallel with his lord Miyoshi Nagayoshi, who divided his own power between courtly politics at Saiin Castle in Kyoto and the more practical governance centered at Iimori Castle.

The Architect

Tamon Castle was constructed on the northern edge of Nara, overlooking the capital's great temples. Its architecture stunned contemporaries, including the Portuguese missionary Luís de Almeida, who described its magnificent, white plastered walls and tiled roofs as something "not to be found in all of Christendom" and likened entering it to arriving in paradise. Key innovations at Tamon included:

• Four-story tower (yagura): Often called the "Taka Yagura" (High Turret), this structure is considered a direct forerunner of the iconic castle keeps (tenshu) that would define later castles.

• Roof tiles : Borrowing from the advanced building techniques of Nara's temples, Hisahide used tiles and thick plaster walls (shikkui), making his castle far more resistant to fire and firearms than the wooden fortifications of the past.

• Tamon-yagura: The castle featured long, house-like defensive structures built atop stone walls, a design so influential it became known as the Tamon-yagura ("Tamon turret") and a standard feature of later Japanese castles.

Hisahide’s defensive network in Yamato included Shigisan and Tamon as his two primary headquarters, complemented by satellite castles such as Sawa Castle and Toichi Castle garrisoned by retainers. Later, his son Hisamichi would use Ryuozan Castle as his base, and in the final conflict with Nobunaga, Kataoka Castle served as a key forward position.

The Survivor

As Hisahide only started to get comfortable with achieving his goals, his world was thrown into chaos. Multiple deaths close to Nagayoshi and Nagayoshi's own failing health drew him away to support Nagayoshi and even cover up his ailing health and eventual death (1564) for two years. Some have taken that as to be an attempt to usurp Miyoshi power but it was clearly Matsunaga carrying out the duties for his deceased compatriot. It is fair to say that without either the other would never have achieved the heights they did.

As the Miyoshi Triumvirate sought to assert dominance over the region, the specter of Oda Nobunaga began to castle a shadow over the horizon. While Hisahide's son Hisamichi participated in the 1565 Miyoshi backed assassination of Shogun Ashikaga Yoshiteru (the Eiroku Incident), contemporary sources suggest Hisahide himself was not a participant.

Soon after, relations soured, and Hisahide found himself at war with the Triumvirs. It was during a 1567 night raid against the Triumvirs who had fortified themselves within Tōdaiji, that the Great Buddha Hall was accidentally burned down—it was not a deliberate act as later tales claimed. Hisahide even supported fundraising for its reconstruction.

In 1568, Hisahide allied himself with Oda Nobunaga, who was marching on Kyoto with Ashikaga Yoshiaki. He submitted to Nobunaga, presenting the famed "Tsukumo" tea caddy as a gift of loyalty. With Nobunaga's powerful backing, he drove the Triumvirs out of the capital region and re-established his control over Yamato. Although allied with Nobunaga he was uneasy under his grip.

His first betrayal of Nobunaga occurred in 1572. He joined the anti-Nobunaga coalition when Takeda Shingen began his march on Kyoto. When Shingen died unexpectedly in 1573, the coalition collapsed. In a rare display of mercy, Nobunaga pardoned him,likely because he still saw use for Hisahide's extraordinary talents, but Hisahide had to surrender Tamon Castle.

Stripped of his domain of Yamato in 1575 and angered by Nobunaga's promotion of his rival Tsutsui Junkei, Hisahide saw a final opportunity when Uesugi Kenshin began his own campaign against Nobunaga in 1577. He fortified himself in his stronghold of Shigisan Castle. This time, there was no escape. Kenshin did not advance, and Nobunaga sent a massive army under his son Nobutada, which included forces led by Akechi Mitsuhide and Hosokawa Fujitaka. After his forward base at Kataoka Castle fell, Shigisan was besieged. On October 10, 1577, Hisahide set fire to the castle's main tower and committed suicide. A popular tale has him destroying the priceless Hiragumo tea kettle coveted by Nobunaga in the act. Many of his vassals fought fiercely to the end, a testament to the loyalty he commanded.

His death sealed his reputation as a cunning and dangerous man. But before the betrayals and rebellion, Hisahide had been something else entirely: a kingmaker, a warrior of remarkable sophistication and a pioneer of castle architecture.

5. The Legacy of a "Villain" Matsunaga Hisahide's legacy is twofold. On one hand, he is the archetypal villain of the Sengoku period, a master of intrigue whose name is synonymous with betrayal. On the other, he was a pivotal figure who ushered in a new era of politics and warfare. His architectural innovations at Tamon and Shigisan castles, particularly the use of multi-story towers, tiled roofs, and the Tamon-yagura, were groundbreaking and directly influenced Nobunaga's own masterpiece, Azuchi Castle. He was also a leading cultural figure, a connoisseur of the tea ceremony whose aesthetic sensibilities were emulated by Nobunaga himself. Perhaps his most profound impact was political. By supporting the Miyoshi regime—a government that functioned effectively without a shogun in Kyoto—Hisahide helped demonstrate that the authority of the Ashikaga shogunate was no longer essential for governing Japan. This precedent was not lost on Oda Nobunaga, who built upon the foundations laid by predecessors like Hisahide. Far from being a mere villain, Matsunaga Hisahide was a complex and brilliant innovator whose life and actions were instrumental in dismantling the old medieval order and shaping the dawn of the early modern era.

Castle Builder

Matsunaga’s legacy as a castle builder is often overshadowed by his political maneuvering, but his fortresses were among the more innovative of the pre-Azuchi era. He built some of the most expansive and well fortified mountaintop fortresses of the time, that rivaled Miyoshi's Iimori Catsle and Akutagawasan Castle.

Takiyama Castle (瀧山城)

Overlooking Kobe Harbor. Opportunity to ally with nearby Miyoshi at Koshimizu Castle. Early stone walls, brilliant double horikiri, steep ascending path

Shigisan Castle (信貴山城)

Built atop a ridgeline between Yamato and Kawachi, Shigisan Castle became Hisahide’s main base. Expanded beginning around 1559, it featured multiple ridgelines fortified with terraced baileys and deep gates. Its location allowed command over three strategic routes — Tatsutagoe, Ikoma-jūsan-tōge, and Hegritani. The design was both militarily sound and symbolically dominant.

Tamon Castle (多聞城)

Constructed in 1560 at the northern edge of Nara, Tamon Castle was Hisahide’s cultural and administrative center. Portuguese missionary Luís de Almeida described it as dazzling, with white walls, golden fittings, and painted fusuma. Its four-story tenshu, layered enclosures, and city-facing presence made it a prototype of the Azuchi-style castles that would come later. Nobunaga visited Tamon in 1574 — two years before Azuchi construction began.

Ryūōzan Castle (龍王山城)

A secondary fort along the Yamato–Kawachi border, Ryūōzan Castle utilized its ridgeline for observation and retreat. Likely functioning as a backup position to Shigisan, its remnants show careful adaptation to terrain and rapid communication with other sites.

Kaseyama Castle (鹿背山城)

Near Kyōtanabe in Yamashiro Province, this lesser-known but technically brilliant fortress features a sophisticated 畝城竪堀 (unejō tatebori) system — deep vertical trenches along narrow ridges. The castle guarded a vital corridor between Nara and Kyoto, and its preservation today is minimal, despite deserving national recognition. Focal point of battles with Miyoshi 3

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Sidebar: “The Three Crimes of Matsunaga Hisahide”

“This man committed three things no one else would dare do.” — Oda Nobunaga

According to later sources, Nobunaga once raised a cup at a banquet and listed Hisahide’s infamous deeds: 1. He killed a shogun. — Ashikaga Yoshiteru (足利義輝) was murdered in 1565 during a coup supported by Hisahide. 2. He overthrew his own lord. — The Miyoshi clan, who had raised him, were dismantled through his betrayal. 3. He burned the Great Buddha Hall. — The Daibutsuden at Tōdaiji (東大寺大仏殿) was destroyed during Hisahide’s conflict with the Miyoshi Triumvirate.

Even Nobunaga — destroyer of Enryakuji — admitted that these were acts beyond even his reach. It was a backhanded tribute to Hisahide’s reputation as a man who combined ruthlessness with spectacle.

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