History has a funny way of burying the people who were actually the smartest in the room. If you look at the Sengoku period in Japan, everyone wants to talk about the "Big Three"—Nobunaga, Hideyoshi, and Ieyasu. They’re the rockstars. But honestly, if you want to understand how to actually survive a world that is literally on fire, you need to talk to Tsutsui Junkei. Or, at the very least, talk about him. He wasn't just another guy with a sword; he was a monk-warrior, a daimyo, and a political chess player who navigated the deadliest era of Japanese history without losing his head. Most people get him wrong. They call him "Hiyori-mi" Junkei—the guy who sits on the fence. But there’s a lot more to the story than just waiting to see which way the wind blows.
Junkei was born into the chaos of Yamato Province. It wasn't a peaceful childhood. By the time he was a teenager, he was already embroiled in a bitter rivalry with Matsunaga Hisahide, a man who basically invented the "villain" trope in Japanese history. Imagine being a young kid trying to hold onto your family’s legacy while a literal warlord is trying to burn your house down. That was Junkei’s Tuesday. He became the head of the Tsutsui clan early, and because the clan had deep ties to the Kofuku-ji temple in Nara, he was a monk. A "Sōhei" vibe, but with the political weight of a daimyo. This duality is why his perspective is so unique.
The Battle of Yamazaki and the "Fence-Sitter" Myth
The biggest reason people still talk to Tsutsui Junkei’s legacy today is the Battle of Yamazaki in 1582. This is the moment that defined him, for better or worse. Oda Nobunaga had just been assassinated at Honno-ji by Akechi Mitsuhide. Suddenly, the entire power structure of Japan collapsed. Mitsuhide was desperate for allies, and he turned to Junkei. They were supposed to be friends, or at least close associates.
But Junkei didn't move.
He stayed at the Horagai pass. He watched. He waited. While Mitsuhide was getting crushed by Toyotomi Hideyoshi’s "Great Chūgoku Return," Junkei was essentially checking his watch. This gave birth to the phrase Hora-ga-toge, referring to someone waiting to see who wins before committing. It sounds cowardly, right? Well, maybe. But if you're a leader responsible for thousands of lives and the survival of a centuries-old lineage, "heroic" suicide isn't always the best business move. He chose survival. He chose his people over a losing cause.
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Why the "Monk" Label Matters
You can't separate the man from the robes. Being a monk wasn't just a fashion choice or a religious obligation; it was a political shield. Yamato Province was a mess of religious influence and secular power. By being a monk-warrior, Junkei could navigate the halls of temples and the war rooms of castles with equal authority. It gave him a layer of "untouchability" that other warlords lacked. When you talk to Tsutsui Junkei through historical records, you see a man who understood that power isn't just about how many samurai you have; it’s about legitimacy.
He was also a man of culture. It’s easy to picture these guys as just bloodthirsty killers, but Junkei was deeply involved in the tea ceremony. He was a student of the legendary Tsuda Sōgyū. Think about that for a second. You spend your morning planning a siege and your afternoon discussing the subtle glaze on a ceramic bowl. This wasn't just a hobby. In the Sengoku period, the tea room was where the real deals happened. It was the "golf course" of the 16th century. If you weren't in the tea circle, you weren't in the loop.
The Rivalry That Defined an Era
You can't talk about Junkei without talking about Matsunaga Hisahide. This guy was the Joker to Junkei's Batman. Hisahide was older, more ruthless, and had a reputation for betraying everyone he ever met. He even allegedly burned down the Great Buddha of Nara. Junkei spent most of his life reclaiming what Hisahide took.
The struggle for Yamato was a grueling, decades-long grind. It wasn't won in one glorious charge. It was won through attrition, diplomacy, and outliving the enemy. Eventually, Nobunaga stepped in and backed Junkei, leading to Hisahide’s spectacular downfall (which ended with Hisahide blowing himself up with a priceless tea kettle because he didn't want Nobunaga to have it).
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- 1566: Junkei loses Tsutsui Castle to Hisahide.
- 1571: The tides turn; Junkei starts gaining the upper hand with Oda's support.
- 1577: Hisahide is finally out of the picture.
Junkei’s victory wasn't just military; it was a victory of temperament. He was the "slow and steady" to Hisahide’s "fast and volatile." There’s a lesson there for anyone dealing with a chaotic environment today. Sometimes, you don't need to be the loudest or most aggressive person in the room. You just need to be the one who is still standing when the dust settles.
Life After the Chaos
After the smoke cleared and Hideyoshi took control, Junkei found himself in a weird spot. He was a survivor, but the new world order was different. He was moved from his ancestral lands in Yamato to Iga Province. This was a huge blow. For a man whose power was so deeply rooted in the soil and temples of Yamato, being uprooted was a death sentence for his influence.
He died shortly after, at the age of 36. It’s a young age by our standards, but in the 1500s, that was a full lifetime. He left behind a legacy that is often unfairly simplified. If you look at the Shingon Buddhism influence in the region today, or the way Nara preserved its identity, you see the fingerprints of the Tsutsui clan.
Modern Lessons from a 16th-Century Strategist
So, why bother to talk to Tsutsui Junkei in 2026? Because we live in a "Yamazaki" world. We are constantly pressured to "pick a side" immediately, to jump on every trend, and to commit to every new movement before we even know if it’s going to survive the week. Junkei reminds us that there is power in the pause.
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- Context is King. Junkei knew that his local power in Yamato was more important than the ego of a failing general like Mitsuhide.
- Cultivate Multiple Identities. He was a warrior, a monk, and a tea master. When one door closed, another opened.
- Know Your Enemy's Weakness. He didn't try to out-crazy Matsunaga Hisahide. He out-waited him.
The "fence-sitter" label is a bit of a smear campaign by later historians who loved the "death before dishonor" samurai trope. But the truth is, most of the people who followed that trope ended up dead and their families erased. Junkei’s lineage survived. His impact on the culture of Nara survived.
If you're looking for a historical figure who represents the "art of the pivot," it’s him. He didn't have the luxury of being a hero; he had the responsibility of being a leader. Next time you're faced with a high-stakes decision where everyone is screaming for you to act, remember the monk-warrior at the pass.
To truly understand this period, look into the specific records of the Tsutsui-shi and their relationship with the Kofuku-ji. You'll find a complex network of land rights, religious tithes, and military alliances that make modern corporate mergers look like child's play. History isn't just about who won the battle; it's about who managed the peace afterward.
Your Strategy Moving Forward
Stop viewing "waiting" as "wasting time." In your own life or career, identify your "Yamazaki moment"—that high-pressure situation where a wrong move could be fatal.
- Analyze the power dynamics like a Sengoku daimyo: Who actually holds the cards?
- Don't be afraid of being called a "fence-sitter" if the fence is the safest place to be while the giants fight.
- Build a "tea room" in your life—a place of high culture and networking that exists outside your primary "battlefield."
Read up on the Tamon-in Nikki, the diary of a monk from that era. It gives a raw, unfiltered look at what it was like to live under Junkei’s rule. It’s not a textbook; it’s a time capsule. By studying the primary sources, you move past the myths and see the man for who he actually was: a survivor in an age of giants.