Another year has passed, which means that the website is another year older. I usually celebrate with a special post or new update, and since The Blog has now become a part of the website, I thought I would share my list of my top 10 figures from the Sengoku Jidai. These are just my picks, mainly based on how much fun I had researching them and how interesting I find them to be. This list was not easy and has even changed over the years as I learn more about the era. I might update this in a few years, but for now, this is how it stands for me.

10. Ashikaga Yoshiteru (March 31, 1536–June 17, 1565)

Starting off the list is the ‘Sword Shōgun’, Ashikaga Yoshiteru. He was the 13^th Ashikaga shōgun and, to many historians, was seen as the last effective shōgun before the clan’s downfall. Even with the Miyoshi clan being a thorn in his side, Yoshiteru was still able to accomplish much, using diplomacy to establish peace between clans. However, when Yoshiteru decided to try and re-establish the shogunate after the death of Miyoshi Nagayoshi in 1564, he was met with opposition from another: Matsunaga Hisahide. The Matsunaga/Miyoshi alliance laid siege to the group of mansions that would later be the grounds for Nijō Castle on June 17, 1565, and Yoshiteru was assassinated.

9. Tōdō Takatora (February 16, 1556–November 9, 1630)

Though I haven’t written an article on him as of writing this post, I’ve learned much about him from Chris Glenn’s biography on him, The Samurai Castle Master: Warlord Todo Takatora (2022). He’s one of the tallest samurai in Japanese history, standing at around 1.9 meters (6’ 2” for my American friends). He served about ten different lords during his lifetime, one of the longest being with Hashiba Hidenaga. He served in Korea and came out of retirement to serve Toyotomi Hideyoshi. Once Hideyoshi passed, he sided with Tokugawa Ieyasu and fought for the Eastern Army at Sekigahara. Aside from his long military record, Takatora was one of the best architects in Japan, with at least twenty castles that can be attributed to him. Such examples include Edo Castle, Wakayama Castle, Uwajima Castle, Imabari Castle, Iga Ueno Castle and Sasayama Castle.

8. Tachibana Ginchiyo (September 23, 1569–November 30, 1602)

The women of this era tend to be forgotten about, which is a shame considering that there are some pretty badass women from this era. One of them is Tachibana Ginchiyo. In a time where men were the ones ruling clans, Ginchiyo is one of the few to do so. Taking over for her father at the age of six, she ran the clan with the help of her father’s retainers until she married Tachibana Muneshige. She was known to have been more interested in martial arts than the ways of being a lady of high class, taking to the battlefield on multiple occasions. She is one of the few I found who became divorced, mainly because she had not given Muneshige any children. Despite this, Ginchiyo still had much influence within the Tachibana clan. She didn’t agree with the Tachibana’s decision to side with Ishida Mitsunari during the Sekigahara Campaign, and after the Western Army’s defeat, both her and her ex-husband were pardoned. She would pass away from illness two years later at the age of thirty-four.

7. Kaihime (c. 1572–17th Century: Exact dates unknown)

Out of all the women I have researched, Kaihime is probably my favorite. Little is known about her, especially when she was born or when she died. What we do know however, paints a picture of one of the toughest women in Japanese history. Her crowning achievement was at the Siege of Oshi Castle, where she sewed together her own armor and defended the castle until the Hōjō surrendered at Odawara. She even led the charge to destroy the dyke that the Toyotomi Army had built to flood the castle. It would be a defeat that Ishida Mitsunari would not recover from, his reputation soiled because he could not take a castle that was being defended by a woman. She was eventually made one of Toyotomi Hideyoshi’s concubines and there are conflicting records with her possible involvement during the Siege of Ōsaka Castle in 1615, with reports saying that she either committed seppuku or that she managed to escape.

6. Oda Nobunaga (June 23, 1534–June 21, 1582)

One of the Three Unifiers had to end up on this list, and out of the three, Oda Nobunaga is the most interesting. Known as the ‘Demon King’, he was the first of the Three Unifiers, laying the groundwork for reunification. He made himself known to Japan at the Battle of Okehazama, defeating the Imagawa Army with only 2,500 men. From there, he would take Kyōto and re-establish the Ashikaga Shogunate. Over the course of the 1570s, he would take on various different clans and the Ikkō-Ikki, the latter sustaining large losses of life due to his actions. He would eventually be assassinated by one of his own at Honnōji in 1582, when Akechi Mitsuhide decided to betray for reasons still unknown to this very day.

5. Date Masamune (September 5, 1567–June 27, 1636)

Kicking off the top five is Date Masamune. He’s high on this list, mainly because he was my introduction to this era of Japanese history. In fact, if you asked me who my top five favorite figures from Sengoku Jidai where several years ago, he would have been at the top of the list. Yet, as I said before, this list is ever changing, and this current list will probably look a lot different in the future.

Known as the ‘One-Eyed Dragon’, he suffered from smallpox as a child which resulted in the removal of his eye. Despite opposition from his own mother, he would succeed as the head of the clan at seventeen, uniting much of the northern domains. He would end up surrendering to Toyotomi Hideyoshi before the Siege of Odawara came to a close and would even serve in Korea for a time. He sided with Tokugawa Ieyasu and fought against the Uesugi in the north, making sure that they were unable to send aid to Sekigahara. After the wars, he established the city of Sendai and sent an expedition around the world, stopping in various places such as the Philippines, Mexico, Spain and Rome. He died in 1636, being one of the few to outlive the age of war they were a part of.

4. Uesugi Kenshin (February 18, 1530–April 19, 1578)

This one surprised even me, yet I got to learn a lot about him recently and slowly became one of my top favorites. ‘The War God of Echigo’ just barely misses out on being in the top three. Originally from the Nagao clan, he takes on the Uesugi name after the then leader of the clan asked for sanctuary after starting a war with the Hōjō clan. He’s most famous for his clashes with Takeda Shingen at Kawanakajima, facing off against him five different times. Despite their rivalry, he would send salt to the Takeda when the Hōjō clan cut their supply after they declared war on their once ally. He also managed to defeat Oda Nobunaga at Tedorigawa in 1577, which would be his final battle. Kenshin would pass the following spring and the Uesugi would spiral into a civil war to determine which of his two adopted sons would control the clan.

Bonus points for the interesting, yet far-fetched theory, that Kenshin was a woman.

3. Saika Magoichi (various years)

Starting out the top three is Saika Magoichi. There are various different people that have been associated with this name, becoming a code name for the leader of the Saika-ikki or the Saika Confederation. The leaders of this famous group have fought against Oda Nobunaga at the ten year siege of Ishiyama Honganji, reportedly served Toyotomi Hideyoshi and fought against the Uesugi with the Date during the Siege of Hasedō. The history of their leaders and group are full of mystery, and I continue to learn more about them every time I revisit the subject.

2. Naoe Kanetsugu (1559–January 20, 1620)

Now here’s a figure that doesn’t get much attention here in the West. Coming in the number two slot is Naoe Kanetsugu, the senior retainer to Uesugi Kagekatsu. He started out serving the Uesugi clan under Kenshin and was later adopted into the Naoe clan following his marriage to Lady Osen. He continued serving the Uesugi under Kagekatsu, fighting alongside his lord as they served under the Toyotomi. After Hideyoshi’s death, the Uesugi sided with Ishida Mitsunari and began being suspected of treason by Tokugawa Ieyasu in the beginning months of 1600. In response to this, Kanetsugu wrote the famous Naoe-jo, calling out Ieyasu for his slander against the Uesugi. This led to a declaration of war, resulting in the Sekigahara Campaign. The Uesugi would be spared at end of it all, and he would spend the remainder of his years building up Yonezawa, the domain the Uesugi would remain at as peace became a reality. Known for his intelligence and loyalty, the survival of the Uesugi clan has been attributed to Kanetsugu.

Though the Naoe-jo that has been circulated might be a fake, it is by far my favorite historical document to read.

Before I reveal who my number one pick would be, here are some honorable mentions:

• Ishida Mitsunari
• Sanada Yukimura
• Bl. Takayama Ukon
• Shima Sakon
• Konishi Yukinaga
• Mochizuki Chiyome

1. Matsunaga Hisahide (1510–November 19, 1577)

Some of you probably saw this coming. If you did, you’ve most likely been with me since the beginning. The article on Matsunaga Hisahide has gone through some changes since it was first posted, but it was my first article on this website. The number one spot goes to the ‘Villain of the Warring States’, Matsunaga Hisahide.

While not much is known about his early life, we do know that he was the governor of Kyōto and had an off again, on again alliance with the Miyoshi, especially after he used the clan to gain control and assassinate the shōgun, Ashikaga Yoshiteru. This control was secured through assassinations of the heirs to the Miyoshi. He would later submit to Oda Nobunaga once the ‘Demon King’ took control of the capital. Though he fought for the Oda, he would try to rebel against him, not once, but twice. He would die at the Siege of Shigisan, with legendary claims stating that he blew up the precious tea kettle, Hiragumo, with gunpowder, killing himself and destroying the one thing Nobunaga wanted.

Considering how I keep learning something new every time I revisit him, Matsunaga Hisahide takes the cake. Then again, I do love a good villain.