Tensions between the Date and the Hatakeyama were beginning to get out of hand. Yoshitsugu, the lord of the Hatakeyama, attempted many times to create peace between the two clans but the hot-blooded Date Masamune refused every time. Yoshitsugu reached out to Masamune’s father, Terumune, to try and mediate the situation. This solution seemed to work pretty well. They ate together, and the next day Yoshitsugu came to visit Terumune in order to thank him for the meal, but once he arrived Yoshitsugu kidnapped Terumune instead. When Masamune discovered this, he flew into a rage, gathered an army, and chased after Yoshitsugu.
They found the kidnappers at Abukuma River. They could have slaughtered them all there, but Yoshitsugu was holding Terumune as a hostage. Terumune shouted for his son to fire on the Hatakeyama, without worrying about his safety, but Masamune hesitated to do something so cold-blooded. In the confusion, his father was killed and Yoshitsugu managed to escape. An enraged Masamune, went to war with the Katakeyama. But Date wasn’t just at war with the Katakeyama, but also their allies including Ashina, Soma, Satake, and many other factions.
Date Masamune with his famous crescent moon helmet
They established an army of 30,000 men against the much smaller Date force of 7,000 men. This army threatened Masamune at Motomiya castle. Masamune organized his force into a defensive position and decided to make use of the fort in his possession. The Hatakeyama quickly took control of three of his four fortresses. After this substantial loss, one of Masamune’s most important retainers was killed in a duel of a Hatakeyama foe. Masamune attempted to defeat the enemy forces at Hitadori bridge but was defeated and forced to retreat back to Motomiya castle. Masamune likely accepted that this was the end. They were vastly outnumbered, had lost any advantages they once had. Every chance they had to turn the tide of the battle had failed. And they now had no choice but to go down honorably.
It would be an easy win for the Hatakeyama now, however, the next day instead of finally crushing their enemies, they chose not to advance. In fact, a large portion of the army packed up and went home instead. The commander of this force had to go and defend his land which was being attacked by one of his enemies. The rest of the force was so dismayed by this, they retreated as well. Miraculously, Date had managed to survive, and he would make sure Hatakeyama and his allies would live to regret the day they ever let him live.
Masamune requested this painting be made with both of his eyes intact
Masamune was a hot-blooded and aggressive man and had been this way since child-hood. Masamune lost the use of his right eye as a child after catching a disease. When a senior member of his clan pointed out that an enemy could grab it fighting him, Masamune ripped it out himself. This, combined with his aggressiveness is how he gained the nickname One-Eyed Dragon of Oshu. In 1589, Masamune bribed a major Ashina retainer to rebel. After this, he put together a large army and marched for the Ashina headquarters at Kurokawa. They fought at Suriagehara.
Masamune demolished the Ashina who were forced to flee, but Masamune would show no mercy. He had cut off their escape route by destroying the Nitsubashi bridge which meant the fleeing men either drowned or were slaughtered. After this victory, Masamune was ordered to work with Toyotomi Hideyoshi and aid him in the siege of Odawara castle. Hideyoshi was essentially the ruler of Japan, so he didn’t have a choice. He did help, but he waited a while for his spies to let him know who the likely winner was before deciding to join. He arrived late because of this.
After the victory, he was treated badly by Hideyoshi and resented this. When the opportunity arrived, he began working with Tokugawa Ieyasu who fought against the Toyotomi loyalists. He helped Tokugawa, established his own Shogunate, and gained a lot in return because of this. The One-Eyed Dragon never stopped being his unusual and aggressive self even as he got older. An example of this is during the 1615 siege of Osaka. Tokugawa’s forces were fighting the remnants of the Toyotomi clan. During the battle, Masamune felt some of his allies weren’t being aggressive enough so he ordered his men to fire some shots in their direction to kick them into gear. During the battle, Masamune fought with another famous samurai, Sanada Yukimura. Yukimura was a hero for the Toyotomi forces, so when he died, their morale died with him and the battle was soon won shortly after.
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