After the death of his father in 1553, Masakatsu left his hometown to serve as an attendant to lord Saitō Dōsan. Dōsan frequently relied upon Masakatsu for conflicts between those in Mino and Owari provinces. Masakatsu’s earlier name of Toshimasa matches an earlier name of Dōsan and is surmised to have been received from Dōsan. In 1556, at the Battle of Nagaragawa between Dōsan and Saitō Yoshitatsu, Masakatsu joined Dōsan’s forces.
In 1585, after Invasion of Shikoku, Hideyoshi awarded him Awa Province as a fief, but he declined in favor of his son, Iemasa, and serving instead as a close adviser of Hideyoshi.