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In [[1570]] Nobunaga, now master of Kyoto, made war against the [[Asakura clan|Asakura]] of [[Echizen province|Echizen]]. Though related to Oda by marriage, Nagamasa was bound by a much longer standing pact of friendship with the Asakura. He consulted his retainer band and almost all of his most important followers advised going to the Asakura's aid. Among the few dissenters was [[Endo Naotsune]], a capable soldier who had earlier opposed allying with Nobunaga and was destined to die in the upcoming battle at [[Battle of Anegawa|Anegawa]]. Nagamasa declared war on Nobunaga and threatened the Oda army from the rear even as it drove into the Asakura lands. Nobunaga, assisted by [[Tokugawa Ieyasu]], was able to withdraw more or less without serious loss, but bore Nagamasa a bitter grudge afterwards. Nobunaga and Ieyasu took an army to reduce Odani in the summer of [[1570]], prompting [[Asakura Yoshikage]] to send an army to Nagamasa's aid. The Asai and Asakura lost the resulting Battle of Anegawa (July 1570), a contest in which the Asai lost Endo Naotsune and hundreds of soldiers. Nagamasa and his Asakura allies replied later that same year with a victory near Otsu that cost Nobunaga a younger brother.  

In [[1570]] Nobunaga, now master of Kyoto, made war against the [[Asakura clan|Asakura]] of [[Echizen province|Echizen]]. Though related to Oda by marriage, Nagamasa was bound by a much longer standing pact of friendship with the Asakura. He consulted his retainer band and almost all of his most important followers advised going to the Asakura's aid. Among the few dissenters was [[Endo Naotsune]], a capable soldier who had earlier opposed allying with Nobunaga and was destined to die in the upcoming battle at [[Battle of Anegawa|Anegawa]]. Nagamasa declared war on Nobunaga and threatened the Oda army from the rear even as it drove into the Asakura lands. Nobunaga, assisted by [[Tokugawa Ieyasu]], was able to withdraw more or less without serious loss, but bore Nagamasa a bitter grudge afterwards. Nobunaga and Ieyasu took an army to reduce Odani in the summer of [[1570]], prompting [[Asakura Yoshikage]] to send an army to Nagamasa's aid. The Asai and Asakura lost the resulting Battle of Anegawa (July 1570), a contest in which the Asai lost Endo Naotsune and hundreds of soldiers. Nagamasa and his Asakura allies replied later that same year with a victory near Otsu that cost Nobunaga a younger brother.  

Nagamasa found himself part of a loose anti-Oda confederation that included the unlikely alliance of Asai, Asakura, Rokkaku, and Enryakuji monks, possibly in cooperation with the shôgun [[Ashikaga Yoshiaki]]. Further attempts by Nobunaga to bring down Odani in [[1571]] and [[1572]] were either thwarted by the appearance of the Asakura army or crises elsewhere. Unfortunately, the death of Nobunaga's most formidable enemy, [[Takeda Shingen]], meant that the full attentions of the Oda could be leveled on Ômi and Echizen. In [[1573]], Nobunaga laid siege to Sawayama Castle, which was held by [[Isono Kazumasa]]. Kazumasa managed to hold out for months but in the end was compelled to surrender. Nagamasa responded by putting Kazumasa's elderly mother, a hostage at Odani, to death. Nobunaga turned against Odani once again, drawing out the Asakura army, which was ambushed and routed before it could reach Nagamasa. Now isolated and seeing the end had come, Nagamasa returned O-ichi and his three daughters to Nobunaga and committed suicide along with his small son, Majumaru.  

Nagamasa found himself part of a loose anti-Oda confederation that included the unlikely alliance of Asai, Asakura, Rokkaku, and Enryakuji monks, possibly in cooperation with the shôgun [[Ashikaga Yoshiaki]]. Further attempts by Nobunaga to bring down Odani in [[1571]] and [[1572]] were either thwarted by the appearance of the Asakura army or crises elsewhere. Unfortunately, the death of Nobunaga's most formidable enemy, [[Takeda Shingen]], meant that the full attentions of the Oda could be leveled on Ômi and Echizen. In [[1573]], Nobunaga laid siege to Sawayama Castle, which was held by [[Isono Kazumasa]]. Kazumasa managed to hold out for months but in the end was compelled to surrender. Nagamasa responded by putting Kazumasa's elderly mother, a hostage at Odani, to death. Nobunaga turned against Odani once again, drawing out the Asakura army, which was ambushed and routed before it could reach Nagamasa. Now isolated and seeing the end had come, Nagamasa returned O-ichi and his three daughters to Nobunaga, and committed seppuku.  Nagamasa's son and only hier, Manpukumaru, was not allowed to live, and was put to the sword Nobunaga.

The Asai's army was considered an effective force and, in fact, at Anegawa, it came very close to defeating Nobunaga's larger force. The Asai relied on the support of their retainer clans, which included the [[Isono clan|Isono]], [[Atsuji clan|Atsuji]], [[Shinjo clan|Shinjo]], [[Akao clan|Akao]], [[Amemori clan|Amemori]], and [[Imai clan|Imai]], and in total could muster some 10,000 men for battle. These troops were equipped with a somewhat higher number of rifles then one might find in a clan of the Asai's means since, during the 1560's, they and the Asakura collaborated on a gun-making workshop at Kunimoto (Ômi).  

The Asai's army was considered an effective force and, in fact, at Anegawa, it came very close to defeating Nobunaga's larger force. The Asai relied on the support of their retainer clans, which included the [[Isono clan|Isono]], [[Atsuji clan|Atsuji]], [[Shinjo clan|Shinjo]], [[Akao clan|Akao]], [[Amemori clan|Amemori]], and [[Imai clan|Imai]], and in total could muster some 10,000 men for battle. These troops were equipped with a somewhat higher number of rifles then one might find in a clan of the Asai's means since, during the 1560's, they and the Asakura collaborated on a gun-making workshop at Kunimoto (Ômi).