Ii Naomasa (井伊 直政?, March 4, 1561 – March 24, 1602) was a general under the Sengoku period Daimyo, and later Shogun, Tokugawa Ieyasu. He is regarded as one of the Four Guardians of the Tokugawa along with Honda Tadakatsu, Sakakibara Yasumasa and Sakai Tadatsugu.
Ii Naomasa was born in Hōda Village of Tōtōmi Province. His family, like the Tokugawa, had originally been retainers of the Imagawa clan, but following the death of the clan's leader, Imagawa Yoshimoto, in the Battle of Okehazama (1560), confusion and general chaos ensued. Naomasa's father, Naochika, was falsely convicted of treason by Yoshimoto's paranoid successor, Imagawa Ujizane, and was subsequently killed. Naomasa, then a very small child, was personally lucky to escape his father's fate and was later taken in by Tokugawa Ieyasu, who discovered Naomasa while hunting in Hamamatsu.
Ii Naomasa joined the ranks of the Tokugawa clan in the mid-1570s, rising swiftly through the ranks to eventually become the master of a sizable holding in Ōmi Province, following the Battle of Sekigahara (1600). His court title was Hyōbu-dayū.
Naomasa initially garnered mass attention at the Battle of Nagakute (1584), commanding around three thousand musketeers with distinction and defeating the forces led by Ikeda Tsuneoki. In the battle, Naomasa fought so valiantly that it elicited praise from Toyotomi Hideyoshi, who was on the opposing side. Following the battle, Hideyoshi's mother was sent to stay with Naomasa in genteel captivity, cementing an alliance between the Tokugawa and the Toyotomi. After Naomasa helped insure victory during the siege of Odawara (1590) by breaching the castle walls and contributing to the Hōjō clan's surrender, he was given Minowa Castle in Kōzuke and 120,000 koku, the largest amount of land owned by any of the Tokugawa retainers.
Naomasa's finest hour was to come at the Battle of Sekigahara, where his unit outpaced those of other generals such as Fukushima Masanori, drawing the "first blood" of that battle. However, as the fighting was dying down, Naomasa was shot and wounded by a stray bullet during his attempt to prevent Shimazu Yoshihiro's getaway, a wound from which he would never fully recover. The wound also prevented his personal involvement in quelling the last vestiges of the anti-Tokugawa faction in the coming months. According to legend, Naomasa was feared so much by his own men, that when he was critically wounded at Sekigahara, not a single one of them committed ritual seppuku, the act of honor killing to prevent a samurai from falling into enemy hands, out of fear of retaliation. As such, Naomasa was able to regain his composure and escape with his life.
The units Naomasa commanded on the battlefield were notable for being outfitted almost completely in blood-red armour for psychological impact, a tactic he adopted from Yamagata Masakage, one of Takeda Shingen's generals. As such, his unit became known as the "Red Devils", a nickname he shared. It has also been rumored, although never confirmed, that Naomasa would sometimes wear a monkey mask into battle, including at Sekigahara.
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