Sondayme Hokague/ Sarutobi and Emma

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In the past, a young Hiruzen, who was the master of the future Sannins, invoked Enma to show the Summoning Jutsu to a young Jiraiya and he could learn to use it. Enma and the 3rd Hokage Enma along with Hiruzen as a young man. Enma participated with his summoner, Hiruzen, in the attack of the Nine-Tailed Fox, where they were taking that beast out of the village. Later, the two are seen near the Kushina barrier watching the Bijū sealing moment