Yoshiaki's path to the shogunate was forged in blood that was not his own. In 1565, his older brother Ashikaga Yoshiteru, the thirteenth shogun, was besieged in his own castle by forces sent by Matsunaga Hisahide and Miyoshi Yoshitsugu. Surrounded and outmatched, Yoshiteru committed seppuku. Yoshiaki, then a minor figure, was captured and confined at Kofuku-ji Temple in Nara. He escaped, fled through Omi Province and Wakasa Province, and eventually found protection in Mino Province under the emerging warlord Oda Nobunaga and his retainer Akechi Mitsuhide. In 1568, Nobunaga's forces swept into Kyoto, crushed the Rokkaku clan's resistance at Kannonji Castle, and installed Yoshiaki as the fifteenth shogun. It was a restoration in name only. Nobunaga immediately imposed the Denchu on'okite -- a set of nine restrictive articles in January 1569, followed by seven more in 1570 -- that stripped the shogunate of real authority. Yoshiaki held the title, but Nobunaga held the power.

By 1572, Yoshiaki had reached his breaking point. He secretly reached out to the Takeda and Matsunaga clans, building a coalition against his patron. The strategy was known as the Nobunaga Encirclement -- an attempt to surround Nobunaga with enemies on all fronts. Yoshiaki and the Matsunaga forces gathered at Makishima Castle, raising the standard of open revolt. Nobunaga's response was swift and ruthless. He marched his armies into the imperial capital, and according to reports, set fire to parts of Kyoto itself to flush out the rebels. The flames that consumed sections of the ancient city were Nobunaga's unmistakable message: no institution, no tradition, no city was sacred enough to shield those who defied him. Yoshiaki fled toward Sakai near Osaka, hoping for sanctuary, but found only degradation -- robbed on the road, mocked by commoners. He renounced his position and took Buddhist vows, shaving his head to disguise himself in hiding.

Yoshiaki's story did not end on that road to Sakai. Sentenced to execution or forced seppuku, he was saved by the intervention of the monk Kennyo of Hongan-ji Temple, who negotiated his banishment to Kawachi Province instead. Yoshiaki sheltered with his brother-in-law Miyoshi Yoshitsugu at Wakae-jo Castle, living as a monk under the name Sho-san. But Nobunaga's reach extended even there -- Oda forces laid siege to Wakae-jo, and Yoshitsugu, betrayed by his own senior vassals, committed seppuku along with his wife and children. Yoshiaki fled again, this time finding refuge with the Mori clan in Bingo Province, where in 1576 he established an extraordinary government in exile at the port town of Tomo-no-Ura. He stubbornly refused to relinquish the title of shogun, issuing orders to feudal lords from a borrowed domain, a ruler without a realm.

The Honno-ji Incident of 1582 -- in which Akechi Mitsuhide turned on Nobunaga, who died by suicide in a burning temple -- briefly rekindled Yoshiaki's hopes. With his tormentor gone, perhaps the shogunate could be restored. He sought support from Mori Terumoto, Toyotomi Hideyoshi, and Shibata Katsuie. But the political landscape had shifted irreversibly. Kobayakawa Takakage of the Mori clan opposed aiding Yoshiaki because of his own alliance with Hideyoshi, and Yoshiaki's alignment with Katsuie put him on the losing side of the succession struggle. By 1585, Hideyoshi had consolidated enough power to become the unofficial ruler of Japan. In 1588, Yoshiaki formally relinquished the title of Seii Taishogun. The Imperial Court granted him the honorific title of Jusangu, a fief of 10,000 koku, and lordship of Makishima Castle in Yamashiro Province -- a quiet retirement for the last shogun of a dynasty that had ruled Japan since 1338.