Battle at Makishima-jo Castle (填島城の戦い)

The Battle at Makishima-jo Castle refers to the battle which occurred between Nobunaga ODA's army and Yoshiaki ASHIKAGA's army from April (March in old lunar calendar) to August (July in old lunar calendar) in 1573. Yoshiaki lost the battle and was expelled from Kyoto, leading to the virtual downfall of the Muromachi bakufu (Japanese feudal government headed by a shogun).

Fire attack in Kamigyo district

Yoshiaki ASHIKAGA, supported by Nobunaga ODA, went to Kyoto and became the fifteenth Shogun of the Muromachi bakufu. At first, he was in a cooperative relationship with Nobunaga, but gradually came into conflict with him because of Nabunaga's attempts to control the Shogun's power, such as Denchu on okite (regulations for the shogunal residence) issued by Nobunaga in 1569. Although Yoshiaki officially had a cooperative relationship with Nobunaga, he formed a coalition against Nobunaga by secretly giving an order of subjugation to Shingen TAKEDA, Nagamasa AZAI, Yoshikage ASAKURA and Kennyo. In 1572, Nobunaga sent an accusatory letter, called Iken 17 kajo (your 17 problems) to Yoshiaki, making their conflict public. "Shincho koki (Biography of Nobunaga ODA)" says that it had already become apparent that Yoshiaki showed a rebellious attitude toward Nobunaga.

Nobunaga had difficulty because of the coalition and was hit with a serious crisis when Shingen TAKEDA started his westward strategy and invaded Higashi Mino Province. However, Shingen's chronic disease worsened around February (January in old lunar calendar) in 1573, and Takeda's army stopped moving. Following this, Nobunaga marched into Kyoto with many soldiers on the 6th of May (25th of March in old lunar calendar). The purpose was to subdugate Yoshiaki ASHIKAGA, who was openly showing hostile behavior, and had raised an army with Hisahide MATSUNAGA, Yoshitsugu MIYOSHI and Miyoshi sanninshu (Nagayuki MIYOSHU, Masayasu MIYOSHI and Tomomichi IWANARI). When Nobunaga went up to Kyoto, Yusai HOSOKAWA and Murashige ARAKI, who had advised Yoshiaki not to raise an army, agreed to Mitsuhide AKECHI's plot, abandoned Yoshiaki, and welcomed Nobunaga at Osaka to side with him.
"Nihonshi (The History of Japan) " written by Luis Frois describes Nobunaga's march to Kyoto with his many soldiers as follows:

As soon as Kyoto citizens heard that Nobunaga was mustering his army to subdugate Kubosama (Shogun), they left Kamigyo and Shimogyo, which were very close to where Yoshiaki stayed. It was horrifying to see the confusion and turmoil of the city. All I could see day and night was nothing but confusion.
People were dragging their household articles; women, children and the aged were fleeing to nearby villages; and grown-ups were wandering about the city crying with their children on their shoulders or in their arms, quite at a loss as to where to go.'

However, Yoshiaki was, even if only in name, Seii taishogun (literally, "the great general who subdues the barbarians"). So, Nobunaga sent Mitsuhide AKECHI and Fujitaka HOSOKAWA as emissaries to Yoshiaki in order to make peace with him on the condition that he would take the tonsure and send hostages. Yoshiaki rejected the offer, surrounded the house of Sadakatsu MURAI, Kyoto shoshidai (the Kyoto deputy) and burned it down on May 11th (March 30th in old lunar calendar).

On May 12th (April 1st in old lunar calendar), Nobunaga ordered his men to set fire to Kamigyo and Shimogyo, the base of Yoshiaki's power, in order to punish him. The merchant class of Kyoto was astounded at the plan and begged Nobunaga to stop setting fires. Kamigyo offered 1,300 silver coins while Shimogyo offered 800 silver coins to Nobunaga. Although Nobunaga stopped setting fire to Shimogyo, he did not forgive Kamigyo, where Shogun's retainers and a lot of merchants supporting Bakufu lived, and set fire to this area.
"Nihonshi" by Luis Frois describes the event as follows:

It was a bloodcurdling, horrible scene; every temple in Kamigyo was burning from midnight till the next day; 50 villages around Kyoto city were burned down; it was as if we were facing Judgment Day. Soldiers and robbers went to priests' quarters and poor priets ran away, after changing their robes into common clothes and hiding their gold, silver and tea utensils in their sleeves or pockets. However, they were robbed of these things and they were even attacked or forced, by torture, to tell the robbers where they had hidden gold and silver.
Soldiers and robbers brutally robbed people repeatedly or even children of their belongings and it was horrible to see their deeds.'

It is said that in Nijo-jo Castle Yoshiaki was terrified to see Nobunaga setting fires to Kamigyo. It is also written in "Nihonshi."

In Kubosama's castle, they saw Kamigyo destroyed and burned down and were deeply terrified and screamed.'

On May 18 (April 7 in old lunar calendar), Nobunaga made peace with Yoshiaki according to Emperor Ogimachi's imperial command of reconciliation.

The Fall of Muromachi bakufu

On May 23 (Apri 12 in old lunar calendar), 1573, in Komanba in Shinano Province, Shingen TAKEDA died of illness, leading to dissolution of the coalition against Nobunaga. In spite of that, Yoshiaki ASHIKAGA abondoned the imperial command, raised yet another army and barricaded himself and his army in Makishima-jo Castle while making Fujihide MITSUBUCHI guard Nijo-jo Castle. However, Nobunaga quickly retaliated and on August 17 (July 10 in old lunar calendar), Nijo-jo Castle, for fear of Nobunaga's force, surrendered to him without bloodshed.

Next, Nobunaga surrounded Makishima-jo Castle. Makishima-jo Castle was an impregnable fortress, located in a towhead of Uji-gawa River, protected by deep fields and a river cay. However, it was impossible to defeat Oda's great army. On August 23 (July 16 in old lunar calendar), Nobunaga attacked Makishima-jo Castle, killed about 50 soldiers of Ashikaga army, and destroyed almost all the castle's defenses. On August 25 (July 18 in old lunar calendar), horrified, Yoshiaki surrendered to Nobunaga, sending Yoshihiro, his eldest son, as a hostage to Nobunaga.

Nobunaga didn't want to be stigmatized as 'the Shogun-killer' by killing Yoshiaki. On August 27 (July 20 in old lunar calendar), he exiled Yoshiaki to Wakae-jo Castle in Kawachi Province, where Yoshitsugu MIYOSHI, his brother-in-law lived.
With that, Muromachi bakufu practically went to ruin. (However, Yoshiaki was still in the position of Seii taishogun and held Jusanmi (Junior Third Rank).)
On December 20 (November 16 in old lunar calendar), Yoshitsugu MIYOSHI was defeated by Nobunaga at the battle of Wakae-jo Castle and Yoshiaki was exiled to Kii Province. Later he escaped into Tomonoura in Bingo Province, asking Terumoto MORI protect him.