TestPage11

Matsunaga Hisahide: From Trader to Traitor

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.

A Brief History

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

Matsunaga Hisahide (松永久秀, 1510?–1577) was one of the most enigmatic figures of the Sengoku period — at once a cultured aesthete, political schemer, and architectural innovator. He rose to prominence under Miyoshi Nagayoshi (三好長慶), the Tenkabito and de facto ruler of Kinai during the mid-16th century. 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.

⸻

Trade and Urban Influence

Matsunaga Hisahide was more than a battlefield tactician; he was a shrewd political broker and urban strategist. Early in his career, his base at Takiyama Castle (滝山城) in Kobe overlooked the port of Hyōgo-tsu (兵庫津), a key Seto Inland Sea trading hub. This early proximity to maritime commerce likely shaped his understanding of the power embedded in trade routes and port access.

Later, as lord of Yamato, Hisahide used his control of Nara and its surrounding road networks to influence the movement of goods and people — particularly those connected to Sakai, the wealthy merchant republic known for its firearms trade. Though he never ruled Sakai directly, he acted as a broker of connections, a power behind the curtain who could grant or deny access.

This intermediary role is dramatized in NHK’s Kirin ga Kuru, where a young Akechi Mitsuhide is sent to Sakai to secure arquebuses with Hisahide’s help. While fictional, the depiction captures an underlying truth: Hisahide operated at the junction of commerce, politics, and culture. He was not a merchant himself — he was the man merchants had to go through.

The Tea Master Daimyō (茶人大名)

In addition to his political ambitions, Matsunaga Hisahide cultivated an image as a refined aesthete. In 1552, he hosted the Takiyama Senku (瀧山千句) — a thousand-verse renga gathering — at Takiyama Castle. This predates the more famous Iimori Senku (飯盛千句) held by Miyoshi Nagayoshi in 1559, and reveals Hisahide’s early role as a tastemaker and cultural patron.

His passion for the tea ceremony was well known. His prized possession, the Hiragumo kettle (平蜘蛛釜), became a symbol of his refined but dangerous persona. When Nobunaga’s forces besieged Shigisan Castle, Hisahide is said to have smashed the kettle before taking his own life — a poetic gesture that may be legend, but reflects the way he fused beauty and brutality.

His mastery of tea was not merely aesthetic. In the Sengoku period, tea gatherings were vehicles for diplomacy, alliance-making, and symbolic power. Hisahide used the tea room as effectively as any war council.

Castle Builder: Fortresses of Power and Aesthetics

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

⸻

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.

⸻

Matsunaga Hisahide defied categorization. He was not simply a traitor, nor merely a patron of culture. He was at the crossroads of commerce, warfare, politics, and art.