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Born in Yonezawa, Dewa Province (present-day Yamagata) as the eldest son of Date Terumune. He lost his right eye to smallpox in childhood and became known as the One-Eyed Dragon. Inheriting the domain at age 18, he pursued a ferocious expansion, subduing most of Mutsu and Dewa by his early twenties to become the greatest lord of Oshu. His victory at the Battle of Suriagehara in 1589 annihilated the Ashina clan of Aizu and marked the peak of his territory. The unification of Toyotomi Hideyoshi, however, forced drastic reductions, and Masamune settled as lord of the Sendai domain with 620,000 koku. He sided with the Tokugawa at Sekigahara, then built Sendai Castle and developed the castle town. In 1613 he dispatched an embassy to the Pope in Rome — the Keicho Mission to Europe — showing an unusually international outlook, and devoted himself to promoting industry, agriculture, and culture in the Sendai domain. He maintained relations with the Edo Shogunate into old age and died in Edo in 1636 at age 70.

Renowned for his bold and magnanimous character, he was a fierce warrior who charged to the vanguard in battle, yet also possessed deep refinement in poetry, cooking, and the tea ceremony. His love of flamboyant design — said to be the origin of the word date (dandy) — made his crescent-moon helmet crest his personal symbol. He combined an unshakeable mental fortitude in adversity with a strategic intelligence that saw ahead of his time.

Through the development of the Tohoku region and the construction of the Sendai castle town, he laid the foundations of modern Sendai city. The Keicho Mission to Europe holds historical significance as one of Asia's earliest diplomatic embassies to the continent. His image as the One-Eyed Dragon commands enormous popularity even today, making him one of the most iconic heroes of the Sengoku era, repeatedly depicted in NHK historical dramas, manga, and popular culture.