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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 set his sights upon Yamato. He set his most trusted general and negotiator Matsunaga Hisahide to this complex task. At the time, Yamato Province, was a region historically dominated by the powerful warrior-monks of Kofukuji and Todaiji temples. There was nominal power by the Tsutsui clan and many smaller local samurai. Hisahide marched on Yamato with 20,000 of Miyoshi's troops in 1559. The invasion was swift and effective. Many local Yamato samurai—including the Ochi, Furuichi, Fukuzumi, and Yagyu clans—resented the Tsutsui and allied themselves with Matsunaga. The primary target was Tsutsui Junkei at Tsutsui Castle. Tsutsui was an ally of Yasumi Munefusa whom Miyoshi was attacking on the Kawachi front. This both secured Yamato for Miyoshi and neutralized the Tsutsui from helping Yasumi.

Hisahide became the first warlord to truly transform Yamato into a unified domain under the control of a single daimyo. He governed with a mix of military force and political accommodation. He established close ties with the wealthy merchants of Nara and Sakai, gave concessions to local allies and worked with the Kofukuji to become the defacto leader of their troops. His rule marked a decisive shift in Nara's history from a city dominated by religious institutions to one governed by warrior authority, a change physically symbolized by the construction of Tamon Castle overlooking the great temples.

Soon after the invasion, Hisahide started renovationing the mountaintop Shigisan Castle as his primary base. This strategic choice high on the mountain range dividing Yamato and Kawachi provinces was a strategic choice. It allowed him to project power into both regions and maintain his commercial ties. A year later in 1561 he started construction of his crowning achievement, the magnificent Tamon Castle. While Shigisan Castle was his permanent military base in the region, Tamon Castle became the political and administrative center, used for diplomacy, cultural events like tea ceremonies, and governing his territories.

This two castle division of purpose reflected Hisahide's governance style. one might say it also reflected his lord Nagayoshi who also split courtly politics between Saiin Castle in Kyoto and actual governance with Iimori castle.

KATAOKA ?

What set Hisahide apart was his effort to integrate himself into the economic and cultural life of the province.

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Hisahide served as Nagayoshi’s chief enforcer and advisor, suppressing rivals and consolidating Miyoshi control across Yamato, Settsu, Kawachi and even excursion into deep Tanba territory.

Following Nagayoshi’s death in 1564, Hisahide aligned briefly with the Miyoshi Triumvirate (三好三人衆), but soon betrayed them, carving out his own power base in Yamato (present day Nara Prefecture). He established Shigisan Castle (信貴山城) as his stronghold, asserting military and political autonomy. This maneuvering put him in direct competition with the rising Oda Nobunaga (織田信長), who initially tolerated Hisahide but later viewed him as a threat.

Hisahide’s final years were marked by shifting allegiances. He submitted to Nobunaga, then rebelled again. In 1577, surrounded at Shigisan Castle, he chose to end his life rather than surrender. According to legend, he destroyed his prized tea kettle — the Hiragumo (平蜘蛛釜) — before committing seppuku, denying Nobunaga the symbolic prize.

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

Matsunaga Hisahide: The Innovator of Yamato Matsunaga Hisahide (1508?–1577) remains one of the most complex and controversial figures of the Sengoku period. For centuries, he has been branded as one of the era’s three great villains (kyōyū), a Machiavellian schemer infamous for committing the “Three Great Crimes”: assassinating the shogun Ashikaga Yoshiteru, betraying his masters the Miyoshi clan, and burning the Great Buddha Hall at Tōdaiji Temple. This reputation, largely cemented by Edo-period tales like the Jōzan Kidan, has long overshadowed his reality. However, recent scholarship, drawing on contemporary records, has begun to re-evaluate this caricature, revealing a man of extraordinary talent—a brilliant administrator, a pioneer of castle architecture, and a refined man of culture whose career profoundly shaped the political landscape of the Kinai region and paved the way for Oda Nobunaga’s ascendancy.

2. Lord of Yamato In 1559, Nagayoshi ordered Hisahide to invade Yamato Province, a region historically dominated by the powerful warrior-monks of Kōfukuji and Tōdaiji temples. The nominal power, the Tsutsui clan, was weakened by internal strife, and many local samurai, resentful of the Tsutsui's alliance with the Kawachi-based Yusa clan, sided with Hisahide's invading army of 20,000 men. This allowed him to swiftly capture Tsutsui Castle and subdue the Yamato Basin (kuninaka) and the eastern plateau (higashi yamauchi). Hisahide became the first warlord to truly transform Yamato into a unified domain under the control of a single daimyo, breaking centuries of clerical rule. His governance was a deft mix of military force and political accommodation. He established a network of castles garrisoned by his trusted retainers, such as the Takayama clan at Sawa Castle and the Mio clan at Tsutsui Castle. Simultaneously, he engaged with the existing power structure, being treated by Kōfukuji Temple as the head of their organized armed forces, the Kanpu-shūto.

What set Hisahide apart was his effort to integrate himself into the economic and cultural life of the province. He established close ties with the wealthy merchants of Nara and Sakai, hosting lavish tea ceremonies in his newly built Tamon Castle. In a notable move, he granted a monopoly on the sale of manjū (sweet buns) in Nara to Hayashi Sōji, a respected scholar, demonstrating an understanding of the importance of commerce and local patronage. His rule marked a decisive shift in Nara's history from a city dominated by religious institutions to one governed by warrior authority, a change physically symbolized by the construction of Tamon Castle overlooking the great temples. 3. A Pioneer of Castle Architecture Hisahide’s strategic vision and aesthetic sense were most brilliantly expressed through his castles, which were revolutionary for their time. While he utilized and expanded existing fortifications, his designs introduced key features that would define the next era of castle architecture. His first major base in Yamato was Shigisan Castle, an existing mountain fortress on the border of Yamato and Kawachi that he occupied and extensively renovated in 1559. Its strategic location was ideal for exercising wide-area control over both provinces. The castle was a massive complex built on Mount Shigi, with a main bailey (honmaru) on the peak and extensive residential compounds, including one known as the "Matsunaga Yashiki," spreading down the radiating ridges. This arrangement, where vassals built their mansions within the fortress alongside their lord, created a fortified city in the mountains. Even more innovative was Tamon Castle, which he began constructing in 1561 on the northern edge of Nara, overlooking the capital's great temples. Tamon was conceived as a multi-functional hub: a military fortress, a political administration center, and a cultural salon. 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: • The first four-story tower (yagura): Often called the "Taka Yagura" (High Turret), this structure is considered a direct forerunner of the iconic castle towers (tenshu) of the Azuchi-Momoyama period. • Widespread use of roof tiles (kawara) and plaster (shikkui): Borrowing from the advanced building techniques of Nara's temples, Hisahide used tiles and thick plaster walls, making his castle far more resistant to fire and firearms than the wooden fortifications of the past. • The origin of the 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 Ryūōsan Castle as his base, and in the final conflict with Nobunaga, Kataoka Castle served as a key forward position. 4. The Post-Miyoshi Years and Final Defeat The death of Miyoshi Nagayoshi in 1564 plunged the Miyoshi clan into a power struggle. Hisahide initially shared control with the "Miyoshi Triumvirs" (Miyoshi Nagayasu, Miyoshi Masayasu, and Iwanari Tomomichi). While Hisahide's son Hisamichi participated in the 1565 assassination of Shogun Ashikaga Yoshiteru (the Eiroku Incident), contemporary sources suggest Hisahide himself was not present. Soon after, relations soured, and Hisahide found himself at war with the Triumvirs. It was during a battle in 1567, a 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 of arson as later tales claimed. Hisahide even supported fundraising for its reconstruction the following year. By 1568, Hisahide was in a precarious position. Astutely reading the political winds, he allied himself with Oda Nobunaga, who was marching on Kyoto with the shogun-aspirant 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. His relationship with key Nobunaga retainers like Akechi Mitsuhide was complex; Mitsuhide served as a mediator for Hisahide's rival Tsutsui Junkei and later acted as a castellan at Tamon Castle after Hisahide surrendered it. Hisahide, however, was a product of the age of gekokujō and adhered to the principle of following the powerful. He betrayed Nobunaga twice: 1. First Betrayal (1572): He joined the anti-Nobunaga coalition when Takeda Shingen began his march on Kyoto. When Shingen died unexpectedly in 1573, the coalition collapsed. Facing overwhelming odds, Hisahide surrendered Tamon Castle. In a rare display of mercy, Nobunaga pardoned him, likely because he still saw use for Hisahide's extraordinary talents. 2. Second Betrayal (1577): 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. 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—coincidentally the tenth anniversary of the Tōdaiji fire—Hisahide set fire to the castle's main tower and committed suicide. The popular tale of him destroying the priceless Hiragumo tea kettle and blowing himself up with gunpowder is a dramatic embellishment from a later period. Many of his vassals fought fiercely to the end, a testament to the loyalty he commanded. 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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