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Eventually Masamori's wife became pregnant and delivered a boy. Masamori was very pleased and cherished the boy, saying, "If the divine message is correct, this boy will rectify this confused world. If not, his son will be the one who does so." The boy was named Masayoshi when he grew up.

From youth Masayoshi preferred military arts to farming, and he served Lord Oda of Kiyosu Castle as a foot soldier. In the battle between his lord and Lord Imagawa Yoshimoto of Suruga province, Masayoshi fought well, but badly hurt his knees. After he returned to his old village, he had his head shaved and called himself Chikuami.

Masayoshi's wife was a daughter of Lord Yasukado, a middle councilor of Mochihagi. As a result of slander, Lord Yasukado was exiled to Owari province. While he was there, he became intimate with a daughter of a local fisherman called Jidaibu and had a daughter. Eventually, Yasukado was pardoned and returned to the capital, promising that he would summon his wife and daughter. But he fell ill and died. The daughter remained with her grandfather and eventually became Masayoshi's wife.

The couple lived happily together, and the wife prayed to the Hiyoshi deity for a son. Soon she dreamed of the sun entering into her bosom, and she delivered a baby boy [Hideyoshi] on the first day of the first month of the year [1536 or 1537]. At that time, a mysterious star as bright as the sun appeared above the house. Later when the boy grew up and fought in battles, the same star always appeared over him and brought him good luck. The boy was born with teeth and looked like a monkey, and although he was named Hiyoshimaru [Good Luck Sun Boy], people called him Monkey.

Thinking of the future of their unusual son, the parents sent him to the Komyoji Temple in the village. They wanted him to learn to read and write so that he could become a priest instead of remaining a mere peasant. But Hideyoshi thought that priests were no different from useless beggars and neglected his studies. He gathered the children of the neighborhood and every day played war games with them using bamboo sticks. He directed his war games standing on a rock, just like a general.

Meanwhile, all the priests of the temple felt Hideyoshi unfit to be a priest and thought of expelling him from the temple. Learning the priests' intention, the angry Hideyoshi reacted violently by beating other children and breaking things, including the principal Buddhist image and sutras. Finally the frightened chief priest sent him home.

Being poor and unable to keep his son at home, Masayoshi entrusted his son with Genzaemon, his wife's merchant cousin, but he stayed at Genzaemon's for only half a year before leaving. After that, he changed his job thirty-eight times while traveling through various provinces. Clever and talented, he could not stand being treated like a slave.

Finally he was hired by a ceramic maker. In the beginning, he worked hard and impressed his master as he learned the business faster and better than his senior colleagues. Soon, however, he became bored with his job and began to neglect his duties, leaving early and returning home late. But the patient master left him alone. One day, when Hideyoshi was looking after the master's small child, he asked himself, "Why am I doing such a useless thing like this and allowing other people to make me feel ashamed?" He tied the child to a pole near a well in the yard and left for Mikawa province, hoping that someone would find the child.