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In early [[1570]], Nobunaga was presented with the first real challenge to his rise. Perhaps in an effort to feel out opposition, Nobunaga had evidently pressed Yoshiaki to request all the local Daimyo to come to Kyoto and attend a certain banquet. One of those who presence was requested was none other than [[Asakura Yoshikage]], the very Daimyo who had frittered his own chance to champion Yoshiaki. Suspecting that Nobunaga was behind the 'invitation', Yoshikage refused, an act Nobunaga declared disloyal to both the shogun and the emperor. With this pretext well in hand, Nobunaga raised an army and marched on Echizen. Initially, all went well for the attackers, with the Asakura revealing their rather lack-luster leadership abilities. By March Nobunaga, supported by Tokugawa Ieyasu (the former Matsudaira Motoyasu), had penetrated Echizen's southern approaches and was moving on Yoshikage's capital (Ichijo-no-tani). Just then, Oda received startling news. His brother-in-law, Asai Nagamasa, had suddenly switched sides and gathered troops to help the Asakura. In fact, Nagamasa's change of heart was probably not as great a surprise as one might think. The Asai and Asakura had been allies for decades, and a single marriage - even if it included the Daimyo of the clan - was not enough to nullify such a long friendship.  

In early [[1570]], Nobunaga was presented with the first real challenge to his rise. Perhaps in an effort to feel out opposition, Nobunaga had evidently pressed Yoshiaki to request all the local Daimyo to come to Kyoto and attend a certain banquet. One of those who presence was requested was none other than [[Asakura Yoshikage]], the very Daimyo who had frittered his own chance to champion Yoshiaki. Suspecting that Nobunaga was behind the 'invitation', Yoshikage refused, an act Nobunaga declared disloyal to both the shogun and the emperor. With this pretext well in hand, Nobunaga raised an army and marched on Echizen. Initially, all went well for the attackers, with the Asakura revealing their rather lack-luster leadership abilities. By March Nobunaga, supported by Tokugawa Ieyasu (the former Matsudaira Motoyasu), had penetrated Echizen's southern approaches and was moving on Yoshikage's capital (Ichijo-no-tani). Just then, Oda received startling news. His brother-in-law, Asai Nagamasa, had suddenly switched sides and gathered troops to help the Asakura. In fact, Nagamasa's change of heart was probably not as great a surprise as one might think. The Asai and Asakura had been allies for decades, and a single marriage - even if it included the Daimyo of the clan - was not enough to nullify such a long friendship.  

At any rate, Nobunaga was placed in a bit of a tricky spot by Nagamasa's defection, but with the stout Tokugawa troops and wiles of [[Hashiba Hideyoshi]] at his disposal, he managed to extricate himself back to Kyoto without great loss. He wasted little time in taking issue with Nagamasa. In July he moved on the Asai's stronghold – [[Odani castle]] - combining his levied troops with a sizable contingent of Tokugawa men for a total of 28,000 soldiers. Asai Nagamasa and [[Asakura Kagetake]] marched out to meet this host, and with their combined 20,000-man army, faced Nobunaga at the Anegawa River. The battle was hotly contested on the part of the Asai, but resulted in a victory for Nobunaga and Ieyasu. It was by no means decisive, but Anegawa represented a turning point in Nobunaga's career, in that while Okehazama may have been a fluke and the Saito and Rokkaku hardly impressive, Nobunaga was a man to be taken seriously.  

At any rate, Nobunaga was placed in a bit of a tricky spot by Nagamasa's defection, but with the stout Tokugawa troops and wiles of Hashiba Hideyoshi at his disposal, he managed to extricate himself back to Kyoto without great loss. He wasted little time in taking issue with Nagamasa. In July he moved on the Asai's stronghold – [[Odani castle]] - combining his levied troops with a sizable contingent of Tokugawa men for a total of 28,000 soldiers. Asai Nagamasa and [[Asakura Kagetake]] marched out to meet this host, and with their combined 20,000-man army, faced Nobunaga at the Anegawa River. The battle was hotly contested on the part of the Asai, but resulted in a victory for Nobunaga and Ieyasu. It was by no means decisive, but Anegawa represented a turning point in Nobunaga's career, in that while Okehazama may have been a fluke and the Saito and Rokkaku hardly impressive, Nobunaga was a man to be taken seriously.  

But Asai and Asakura proved tenacious opponents. Later in 1570, they led another combined army along the coast of Lake Biwa and defeated an Oda army near Otsu, killing one of Nobunaga's own brothers, Nobuharu. In a significant development, the warrior-monks of Mt Hiei lent their support to the Asai and Asakura, a fatal error, as Nobunaga would ruthlessly prove in late [[1571]]. In the meantime, Nobunaga found Ikko and warrior-monk resistance to his expansion stiffening at every turn. In Kwatchi, the warrior-monks of the Ishiyama Honganji fortress, well equipped with firearms, assisted the Miyoshi in their struggle against the Oda. In Ise, the Ikko-ikki of the Nagashima area openly defied Nobunaga and would cause him considerable difficulty until he dealt with them in [[1574]]. An early struggle with the Ikko of Ise had already claimed the life of Nobunaga's brother Nobuoki ([[1569]]) and a preliminary assault in May of [[1571]] on Nagashima developed into a complete and costly fiasco.  

But Asai and Asakura proved tenacious opponents. Later in 1570, they led another combined army along the coast of Lake Biwa and defeated an Oda army near Otsu, killing one of Nobunaga's own brothers, Nobuharu. In a significant development, the warrior-monks of Mt Hiei lent their support to the Asai and Asakura, a fatal error, as Nobunaga would ruthlessly prove in late [[1571]]. In the meantime, Nobunaga found Ikko and warrior-monk resistance to his expansion stiffening at every turn. In Kwatchi, the warrior-monks of the Ishiyama Honganji fortress, well equipped with firearms, assisted the Miyoshi in their struggle against the Oda. In Ise, the Ikko-ikki of the Nagashima area openly defied Nobunaga and would cause him considerable difficulty until he dealt with them in [[1574]]. An early struggle with the Ikko of Ise had already claimed the life of Nobunaga's brother Nobuoki ([[1569]]) and a preliminary assault in May of 1571 on Nagashima developed into a complete and costly fiasco.  

By 1571 Nobunaga's position, while not in grave danger, was becoming a difficult one. Now actively arrayed against him were the Asai, Asakura, and Miyoshi clans, supported by Ikko and warrior monks from the Honganji, Enryakuji (of Mt. Hiei), Negoroji, and Nagashima. The Honganji proved the most formidable: head priest [[Kennyo Kosa]] and the Honganji's fanatical adherents were destined to hold out for a decade, in time supported by the Mori clan.  

By 1571 Nobunaga's position, while not in grave danger, was becoming a difficult one. Now actively arrayed against him were the Asai, Asakura, and Miyoshi clans, supported by Ikko and warrior monks from the Honganji, Enryakuji (of Mt. Hiei), Negoroji, and Nagashima. The Honganji proved the most formidable: head priest [[Kennyo Kosa]] and the Honganji's fanatical adherents were destined to hold out for a decade, in time supported by the Mori clan.  

In the winter of 1572, Takeda led a large army down from Shinano into Totomi and threatened Ieyasu's headquarters at Hamamatsu. Nobunaga sent a few thousand men under three generals of mixed quality - not enough to stave off the defeat that followed but enough to eliminate any pretext of civility that may have existed between Nobunaga and Shingen. At the same time, Takeda troops actually penetrated Mino, and captured the imposing Iwamura castle - an embarrassing event that no doubt made Oda furious.  

In the winter of 1572, Takeda led a large army down from Shinano into Totomi and threatened Ieyasu's headquarters at Hamamatsu. Nobunaga sent a few thousand men under three generals of mixed quality - not enough to stave off the defeat that followed but enough to eliminate any pretext of civility that may have existed between Nobunaga and Shingen. At the same time, Takeda troops actually penetrated Mino, and captured the imposing Iwamura castle - an embarrassing event that no doubt made Oda furious.  

Fortune was destined to smile on Nobunaga in [[1573]], however. By that May, Takeda Shingen was dead. While the specifics of his passing remain something of a mystery, the loss of Shingen would ultimately prove fatal to the Takeda clan and a boon for Nobunaga. The timing certainly could not have proved worse for Ashikaga Yoshiaki, who in March had fortified [[Nijo castle]] and dispatched letters to Nobunaga's enemies, urging them onward. While Shingen threatened, Nobunaga had been unable to respond to the shogun's defiance, save for making a few good will overtures to Yoshiaki.  

Fortune was destined to smile on Nobunaga in 1573, however. By that May, Takeda Shingen was dead. While the specifics of his passing remain something of a mystery, the loss of Shingen would ultimately prove fatal to the Takeda clan and a boon for Nobunaga. The timing certainly could not have proved worse for Ashikaga Yoshiaki, who in March had fortified [[Nijo castle]] and dispatched letters to Nobunaga's enemies, urging them onward. While Shingen threatened, Nobunaga had been unable to respond to the shogun's defiance, save for making a few good will overtures to Yoshiaki.  

The Takeda clan had endeavored to keep Shingen's death a secret, but it seems likely that Nobunaga at least intuited the truth. With all of the furious determination he would become famous for, Nobunaga turned on his remaining enemies in the Chubu region. On 3 May he surrounded Kyoto and caught Yoshiaki unprepared, forcing the shogun to negotiate. An uneasy truce was arranged through the intercession of the Emperor, one that neither side expected to hold for long. In the meantime, Nobunaga took charge of operations against the Nagashima Ikko stronghold and led an army there in July. He was defeated in a sharp struggle and forced to retreat, an embarrassing setback that may have helped goad Yoshiaki into rebelling again in the first week of August. Leaving [[Mizubuchi Fujihide]] in charge of Nijo, Yoshiaki barricaded himself in a fort astride the Uji River. His intention evidently was to hold off Nobunaga long enough for the Asai, Asakura, and Honganji to fall on Oda from behind. In fact, Yoshiaki's position was strong - but in the event not strong enough. Realizing the danger inherent in Yoshiaki's recalcitrance, Nobunaga acted swiftly. He assaulted Yoshiaki's stronghold and by 18 August had breached the fort's outer defenses. Yoshiaki sued for peace and pleaded for his life - a request Nobunaga granted. Instead, Yoshiaki was exiled, the last of the Ashikaga shoguns. From now until his death, Nobunaga would act as the de facto Shogun.  

The Takeda clan had endeavored to keep Shingen's death a secret, but it seems likely that Nobunaga at least intuited the truth. With all of the furious determination he would become famous for, Nobunaga turned on his remaining enemies in the Chubu region. On 3 May he surrounded Kyoto and caught Yoshiaki unprepared, forcing the shogun to negotiate. An uneasy truce was arranged through the intercession of the Emperor, one that neither side expected to hold for long. In the meantime, Nobunaga took charge of operations against the Nagashima Ikko stronghold and led an army there in July. He was defeated in a sharp struggle and forced to retreat, an embarrassing setback that may have helped goad Yoshiaki into rebelling again in the first week of August. Leaving [[Mizubuchi Fujihide]] in charge of Nijo, Yoshiaki barricaded himself in a fort astride the Uji River. His intention evidently was to hold off Nobunaga long enough for the Asai, Asakura, and Honganji to fall on Oda from behind. In fact, Yoshiaki's position was strong - but in the event not strong enough. Realizing the danger inherent in Yoshiaki's recalcitrance, Nobunaga acted swiftly. He assaulted Yoshiaki's stronghold and by 18 August had breached the fort's outer defenses. Yoshiaki sued for peace and pleaded for his life - a request Nobunaga granted. Instead, Yoshiaki was exiled, the last of the Ashikaga shoguns. From now until his death, Nobunaga would act as the de facto Shogun.