Masahide first served Oda Nobuhide. He was a talented samurai as well as skilled in sado and waka. This helped him to act as a skilled diplomat, dealing with the Ashikaga shogunate and deputies of the emperor. In 1547 Nobunaga finished his coming-of-age ceremony, and on the occasion of his first battle, Masahide served beside him. Masahide served the Oda family faithfully in many ways, but he was also deeply troubled by Nobunaga's eccentricity. After Nobuhide's death, discord in the clan increased and so did Masahide's concern about the future of his master. In 1553, Masahide committed (kanshi) to startle Nobunaga into his obligations.