The siege of Odawara in 1590 was a major battle in the history of Japan, marking the end of the Sengoku period and the beginning of a new era of peace and stability under the Tokugawa Shogunate. The siege lasted for almost three months and involved some of the most skilled military commanders of the time.

Background
Odawara Castle was located in the province of Sagami, which was controlled by the powerful Hojo clan. The castle was one of the most well-fortified in Japan, with high walls, multiple moats, and numerous defensive structures. The Hojo clan of Odawara had been a major player in Japanese politics for about a century and had successfully repelled several attempts to take the castle by force. However, in the late 16th century, the Hojo clan's power began to decline. The Tokugawa clan, led by Tokugawa Ieyasu, had become increasingly powerful and had allied with other regional lords to form a coalition against the Hojo. In 1590, Toyotomi Hideyoshi, the most powerful ruler in Japan at the time, launched a massive campaign against the Hojo clan, with the aim of taking control of Odawara Castle and securing his position as the supreme ruler of Japan.

The Siege
Hideyoshi's forces consisted of over 200,000 soldiers, including some of the most skilled warriors in Japan. The defenders of Odawara Castle were well-prepared for the siege and had ample supplies of food and water. The first phase of the siege involved a blockade of the castle, with Hideyoshi's forces surrounding the fortress and cutting off all supply lines. The defenders responded by launching frequent sorties, attempting to break through the enemy lines and gather supplies. The siege quickly became a stalemate, with both sides suffering heavy losses. In an attempt to break the deadlock, Hideyoshi ordered the construction of a series of earthworks and trenches around the castle. The earthworks were designed to protect his soldiers from the castle's defenders and to allow his artillery to get closer to the walls. The defenders responded by launching a series of counterattacks, attempting to destroy the earthworks and prevent the enemy from advancing. However, the defenders were outnumbered and outgunned, and their attacks were largely unsuccessful. The turning point of the siege came when Hideyoshi ordered a massive assault on the castle's main gate. The gate was one of the most heavily defended areas of the castle, but Hideyoshi's forces managed to breach the walls and enter the castle grounds. The defenders fought fiercely, but they were outnumbered and outmatched. After a long and brutal battle, the defenders were forced to retreat to the castle's inner keep, where they made their last stand.

About three months after the siege of Odawara had begun, the sudden of appearance of Ishigakiyama Ichiya Castle on a mountain top overlooking Odawara Castle dealt a psychological impact that spend the surrender of the remaining defending forces. Hojo Ujimasa and his brother Ujiteru were forced to commit suicide after the end of the siege. The castle and surrounding land was given to Tokugawa Ieyasu, on of Hideyoshi's top generals. Tokugawa Ieyasu would later become shogun and his family would rule Japan from 1603-1868 during the Edo Period establishing the city that would later become Tokyo.