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As a young acolyte Ekei had caught the attention of [[Mori Motonari|Môri Motonari]], who had ordered him into his service. A man of exceptional intelligence and insight, Ekei accompanied Motonari on most of his campaigns, who enjoyed conversing with his "little monk". When Motonari died in [[1572]], Ankokuji traveled about for some time before returning to serve [[Mori Terumoto|Môri Terumoto]] and becoming the abbot of the [[Ankoku-ji]]. Later, during the long war with the [[Oda clan|Oda]], Ekei would act as a negotiator with Hideyoshi, whom he had met in [[1573]]. Hideyoshi developed a fondness for Ekei, and awarded him a fief worth 60,000 koku in [[Iyo province]] (Shikoku). Ekei became a member of Hideyoshi's close entourage, along with [[Hosokawa Fujitaka]] and [[Sen no Rikyu]].  

As a young acolyte Ekei had caught the attention of [[Mori Motonari|Môri Motonari]], who had ordered him into his service. A man of exceptional intelligence and insight, Ekei accompanied Motonari on most of his campaigns, who enjoyed conversing with his "little monk". When Motonari died in [[1572]], Ankokuji traveled about for some time before returning to serve [[Mori Terumoto|Môri Terumoto]] and becoming the abbot of the [[Ankoku-ji]]. Later, during the long war with the [[Oda clan|Oda]], Ekei would act as a negotiator with Hideyoshi, whom he had met in [[1573]]. Hideyoshi developed a fondness for Ekei, and awarded him a fief worth 60,000 koku in [[Iyo province]] (Shikoku). Ekei became a member of Hideyoshi's close entourage, along with [[Hosokawa Fujitaka]] and [[Sen no Rikyu]].  

Although a priest by trade, Ekei led men for both [[Toyotomi Hideyoshi|Hideyoshi]] and Môri Terumoto. In the [[Odawara Campaign]] ([[1590]]) he was present at the [[Siege of Shimoda]] and in the Korean Campaigns ([[1592]]-[[1593|93]], [[1597]]-[[1598|98]]) he served on Terumoto's staff. Letters sent by Ekei to Terumoto further indicate that Ekei's duties went beyond advice - although his advice would prove most important and unfortunate for the future of the Môri after Hideyoshi's death.  

Although a priest by trade, Ekei led men for both [[Toyotomi Hideyoshi|Hideyoshi]] and Môri Terumoto. In the [[Odawara Campaign]] ([[1590]]) he was present at the [[Siege of Shimoda]] and in the [[Korean Invasions|Korean Campaigns]] ([[1592]]-[[1593|93]], [[1597]]-[[1598|98]]) he served on Terumoto's staff. Letters sent by Ekei to Terumoto further indicate that Ekei's duties went beyond advice - although his advice would prove most important and unfortunate for the future of the Môri after Hideyoshi's death.  

When lines were drawn in [[1600]] between [[Ishida Mitsunari]] and [[Tokugawa Ieyasu]], Ekei threw in with the former, and exerted considerable pressure on Môri Terumoto to do the same, ultimately prevailing over the more cautious counsel of [[Kikkawa Hiroie]]. At the [[Battle of Sekigahara]], Ekei commanded a contingent of 1,800 men on Nangu Hill, positioned near the troops of Hiroie and Natsuka Masaie. When the main armies became engaged around Sekigahara village, Ekei and the Môri troops (commanded by [[Mori Hidemoto|Môri Hidemoto]]) decided to enter the fray, and waited on Hiroie, the Môri's vanguard force, to move. Unbeknownst to them, Hiroie had negotiated a secret agreement with Ieyasu, and had no intention of moving anywhere. Ekei and his closest neighbor, Natsuka, hardly soldiers, both lacked the resolve to do anything one way or the other, and so the 25,000 troops under the Môri and the Chosokabe sat idle. This inactivity sealed a defeat precipitated by the treachery of [[Kobayakawa Hideaki]], and once the issue was clearly decided, Ekei and his fellow commanders thought it best to beat a hasty retreat. Ekei himself endeavored to escape in a palanquin to the To-ji, but was captured, according to legend by a rônin who held an old grudge against him. Tokugawa sentenced him to die by beheading on Kyoto's Rokujo-ga-hara, both as a lesson and perhaps in view of his non-samurai status. He was duly beheaded there along with [[Konishi Yukinaga]] and Ishida Mitsunari.

When lines were drawn in [[1600]] between [[Ishida Mitsunari]] and [[Tokugawa Ieyasu]], Ekei threw in with the former, and exerted considerable pressure on Môri Terumoto to do the same, ultimately prevailing over the more cautious counsel of [[Kikkawa Hiroie]]. At the [[Battle of Sekigahara]], Ekei commanded a contingent of 1,800 men on Nangu Hill, positioned near the troops of Hiroie and Natsuka Masaie. When the main armies became engaged around Sekigahara village, Ekei and the Môri troops (commanded by [[Mori Hidemoto|Môri Hidemoto]]) decided to enter the fray, and waited on Hiroie, the Môri's vanguard force, to move. Unbeknownst to them, Hiroie had negotiated a secret agreement with Ieyasu, and had no intention of moving anywhere. Ekei and his closest neighbor, Natsuka, hardly soldiers, both lacked the resolve to do anything one way or the other, and so the 25,000 troops under the Môri and the Chosokabe sat idle. This inactivity sealed a defeat precipitated by the treachery of [[Kobayakawa Hideaki]], and once the issue was clearly decided, Ekei and his fellow commanders thought it best to beat a hasty retreat. Ekei himself endeavored to escape in a palanquin to the To-ji, but was captured, according to legend by a rônin who held an old grudge against him. Tokugawa sentenced him to die by beheading on Kyoto's Rokujo-ga-hara, both as a lesson and perhaps in view of his non-samurai status. He was duly beheaded there along with [[Konishi Yukinaga]] and Ishida Mitsunari.