Date Masamune, born in 1567, is one of the most famous daimyo of Japan due to his unique character and militaristic accomplishments. Known for his Dokuganryuu, or One-Eyed Dragon, nickname and his helmet adorned with a huge crescent moon, he almost single-handedly unified Northern Japan with great ferocity and continued to rule as a political juggernaut for four decades through cunning and insight. During his early years, Masamune lost favor with father and mother due to their belief that his lack of one eye would bring doom to the Date clan. This led to several internal conflicts within the Date clan that delayed Masamune’s conquest of Northern Japan and, by the time of his success, Hideyoshi Toyotomi had already risen to power so Masamune had no choice but to become Hideyoshi’s vassal. He eventually became an ally of Tokugawa Ieyasu during the Battle of Sekigahara and was responsible for preventing the Uesugi clan (and Naoe Kanetsugu) from reinforcing the Toyotomi’s vassal army. While Masamune extremely valued loyalty, it is possible he shifted allegiances after Hideyoshi’s order to execute Masamune’s adopted son due to fear of rebellion against Hideyoshi’s young heir.

Masamune was an icon in Japan who was made more infamous due to his missing eye. He was nicknamed dokuganryu, which translates to the “one-eyed dragon”...

Until his death in 1636, Masamune was considered a ‘wild card’ in terms of his attitude towards Japan. He valued Christianity and encouraged traveling to foreign countries to understand their technological advancements – he even sent a letter to the Pope trying to establish ties for a potential alliance. Furthermore, he engaged in cookery and the arts – such practices often considered ‘beneath’ him due to his high status. 

His lasting success, along with his unique personality, has allowed for Masamune to remain as one of the more popular historical figures in modern Japan. Masamune notably funded and backed one of Japan's few journeys of far-flung diplomacy and exploration in this period. He ordered the building of the exploration ship Date Maru or San Juan Bautista, using foreign (European) ship-building techniques. He sent one of his retainers, Hasekura Tsunenaga, Sotelo, and an embassy numbering 180 on a successful voyage to establish relations with the Pope in Rome. This expedition visited such places as the Philippines, Mexico, Spain and Rome. Previously, Japanese lords had never funded this sort of venture, so it was probably the first successful voyage. At least five members of the expedition stayed in Coria (Seville) of Spain to avoid the persecution of Christians in Japan. 600 of their descendants, with the surname Japón (Japan), are now living in Spain.