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From Yamashiro Province (or Omi Province by some accounts), he is said to have been born the son of an oil merchant or to have been a monk called Horenbō — though recent research favors the theory that the gekokujo was accomplished over two generations, by Dosan and his father Nagai Shinsaemon-no-jo. Operating under the name Nagai Norihide, he served the Toki clan lords of Mino Province — Yorishige and Yoriaki — and gradually usurped real power by exploiting their authority. In 1542 he expelled Toki Yoriaki and became lord of Mino Province, taking the name Saito Toshimasa (Dosan). In 1548, while in conflict with Oda Nobuhide, he married his daughter Kikyo (Nohime) to Nobuhide's eldest son Nobunaga (then 15), and later met with Nobunaga in person — the story of how he recognized Nobunaga's extraordinary talent at that meeting is famous. In his final years he fell into conflict with his own son Yoshitatsu, and in 1556 was defeated and killed by Yoshitatsu's forces at the Battle of the Nagara River. He was 63 (or 62 by some accounts).

A master of intrigue, embodying gekokujo with ruthless and bold decisiveness. True to his nickname "Dosan the Viper," he possessed a tenacious grip that never released his prey once he had bitten down, and a venomous strategic mind. At the same time he had the eye to immediately recognize Oda Nobunaga's genius, and also possessed cultural refinement. He is also known for leaving a testament that seemed to anticipate his own death.

As the father of Nohime (Kicho), Nobunaga's official wife, he was indirectly involved in a turning point of the warring states period through his connection to Oda Nobunaga. He is also remembered as the archetypal example of gekokujo, embodying the spirit of a warring states era in which the capable could rise above their station through ability alone. Sites associated with Dosan remain at Jozaiji temple in Gifu Prefecture and along the banks of the Nagara River.