The site where Takasaki Castle would rise had already been fought over for centuries. During the late Heian period, the Wada clan controlled the area, building a fortified manor on the banks of the Karasu River. Through the Muromachi period, the Wada served the Uesugi clan, but in 1561, Wada Narishige defected to the rival Takeda clan in a dispute over leadership, and his son Wada Nobunari later aligned with the Odawara Hojo. That decision proved fatal. In 1590, Toyotomi Hideyoshi dispatched an army under Uesugi Kagekatsu and Maeda Toshiie to crush the Hojo strongholds, and Wada Castle was destroyed. The ruins lay along the Karasu River, waiting.

When Tokugawa Ieyasu took control of the Kanto region in 1590, he stationed one of his most trusted warriors, Ii Naomasa -- one of the celebrated Four Generals -- at nearby Minowa Castle. But in 1597, Ieyasu ordered Naomasa to build a new fortification on the old Wada ruins, recognizing that the site commanded a critical crossroads. Naomasa relocated in 1598, renamed the place Takasaki, and brought the entire population of Minowa with him to form the core of a new castle town. After the Battle of Sekigahara in 1600, the Ii clan was transferred to Omi Province, and Takasaki began its long parade of rulers -- the Sakai, the Ando, and several branches of the Matsudaira. The Okochi Matsudaira arrived in 1695 and held the castle until the end of the Edo period, with only a brief interruption between 1710 and 1717.

In 1619, Ando Shigenobu launched an ambitious reconstruction that would stretch across three generations and seventy-seven years. The project produced a three-story donjon at the center, flanked by two-story yagura watchtowers at each of the four cardinal directions. The castle complex grew into a formidable arrangement of baileys and moats along the Karasu River. Yet Takasaki's most infamous moment had nothing to do with siege warfare. In 1633, the shogun exiled his own brother Tokugawa Tadanaga to the castle after political disputes, then ordered his death by seppuku that same December. The room where Tadanaga died -- a shoin reception hall -- survived the centuries and now stands on the grounds of the Buddhist temple Chosho-ji, where it serves as the priest's residence.

The Meiji Restoration of 1873 ended the feudal era, and Takasaki Castle was swiftly dismantled. Most structures were destroyed or sold off, and the moats were filled in. By the time World War II ended, the Imperial Japanese Army's 15th Infantry Regiment occupied much of the former grounds. Today, Takasaki's city hall and public library sit where castle baileys once stood. But fragments survived. A yagura watchtower remained in private hands until 1974, when Takasaki city purchased it and relocated it to one of the original stone foundations in the Third Bailey. A castle gate followed in 1980, also repurchased and returned to the grounds. These reconstructed remnants, standing among cherry trees and administrative buildings, mark the outline of a fortress that once governed the crossroads of an empire.