Date Masamune is one of the most famous feudal era daimyo of Japan. Nicknamed Dokuganryuu ("One/Single-Eyed Dragon") by later generations, and known for 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, especially in regards to foreign trade, Christianity and allegiances. He was an ally of Tokugawa Ieyasu during the Battle of Sekigahara and later during the Siege of Osaka.
Born Bontenmaru, he married at thirteen, won his first battle at fifteen, and became head of the clan at eighteen, but his mother Yoshihime never approved of him since he lost an eye to smallpox as a child. When he came to power, he decided that the Date Clan shouldn't be so submissive and so went on the offensive, conquering the neighboring clans. This ended up sorta biting him in the ass as one of the clans, the Hatakeyama, decided to take his father Terumune hostage to force him to pull his forces back. When Masamune confronted the Hatakeyama, Terumune instead told Masamune to just open fire and kill him along with the Hatakeyama. Masamune did so... and then hunted down the rest of those Hatakeyama supporters and tortured them as retribution.
With his father gone, Masamune continued his conquest, hindered only by a power struggle within his family: his mother, who favored his younger brother Masamichi, allegedly went as far as poisoning him. In the end Masamune killed his brother and disinherited him for seven generations(!) so no descendant of his would be a threat to Masamune's and his heirs' position. Yoshihime fled back to her home and Masamune never saw her again (which apparently did wonders to their relationship, as they seem to have reconciled with time).
Masamune succeeded in unifying the north, but by the time he did so, Toyotomi Hideyoshi had already risen to power, so Masamune had no choice but to become Hideyoshi's vassal (though he was rather unenthusiastic about it). Under Hideyoshi's banner he took part in in eliminating the Hojo at Odawara and was rewarded, moving to Sendai (in the region ravaged by the 2011 earthquake/tsunami) as his home base and turning it from a small rural community into a prosperous city. He eventually allied with Tokugawa Ieyasu against an aging Hideyoshi, and aided him in seizing power following Hideyoshi's death. It took a long time for him to give up his dream of ruling all Japan, but after he finally realized he had no chance, he was a loyal and steadfast ally. Although considered a Wild Card and not really trusted by anyone, Masamune did prove his loyalty and even recited a poem when Ieyasu was on his deathbed.
He kept several Christians under his protection (his favourite daughter may or may not have converted) and encouraged travel to foreign countries, even sending a letter to the Pope trying to establish ties for a potential alliance. He was also greatly interested in cookery and art, and possessed a rather flamboyant taste, leading folk etymology to assign the kanji of his surname to the word date (approx. "flashy").
His lasting success, along with his unique personality, means Masamune has remained as one of the more popular historical figures in modern Japan.
Notable people that were around Masamune's rule:
- Date Terumune: His father, as mentioned above. About one of the few people Masamune respected.
- Yoshihime: His mother, and as mentioned, she does not like him, going so far as poisoning him later, then fled to her homeland Mogami (she's the sister of the daimyo Mogami Yoshiaki), though as said, their relationship eventually got better. Most fictions tend to soften this antagonism if they included her, usually making her a Well-Intentioned Extremist and overall just flat out avoids making her an Evil Matriarch.
- Megohime: His wife. Not much is known from her except she's from the Tamura clan (one of the clans that Masamune later crushed) and she's usually loyal to him and bore him his children. And for some reason, she's kind of... popular for a woman that does not do much in that era, as far as Date women goes.
- Katakura Kagetsuna: Or better known as Katakura Kojuro, this is without a doubt the most well known retainer of Masamune, they're pretty much friends since childhood and often acts the brains behind Masamune, influencing his actions for the good of the clan, including the surrender to Hideyoshi. He's also noteworthy of saving Masamune's butt in his first battle by fooling the enemy with claiming that he's him so the enemy gets distracted. Usually being portrayed as the Blue Oni with Masamune being the Red Oni.
- Date Shigezane: Masamune's cousin, and considered one of his most powerful retainers, pretty much they and Kojuro form a Power Trio amongst the Date army. His most noteworthy feature is his helmet that has a centipede ornament on it.
- Katakura Kita: Kojuro's big sister. She doesn't do much in terms of warfare or civil problems, but she became Masamune's wet nurse, so basically without her, he might have grown up differently when you realize his actual mother was Yoshihime (at her worst)...
Tropes as portrayed in fiction:
- Cultured Badass: He's into a lot of Western cultures, becoming a patron for Christianity, reads poems for Tokugawa Ieyasu (also on his deathbed) and he's a badass when it comes to the art of war.
- Eyepatch of Power: Subverted - he always wears an eyepatch in fictional depictions, but there's no record of him wearing one in real life. In fact, he specifically requested that his portraits be painted with him having both eyes. The reason for the latter is a bit of Values Dissonance in the West—in East Asia the body is considered a gift from the parents, and alienating any part of it, even due to reasons beyond one's control, is considered disrespectful.
- Real Men Cook: He tends to hold banquets, makes sure they're eloquent to fit his Cultured Badass status... and he cooked the meals himself.
Works that reference Masamune:
- Mitsuteru Yokoyama — of Sally the Witch, Giant Robo, God Mars and Gigantor fame — wrote a biographical manga called Date.
- NHK drama film Dokuganryuu Masamune, starring a young Ken Watanabe. Obviously about Masamune.
- Samurai Warriors included him in the first game as a Bratty Half-Pint who'd interrupt nearly every battle and beat the crap out of both sides. He's Dual Wielding two bokkens in that game. From the second game onwards, he got a Plot-Relevant Age-Up and now wields a saber in one hand, and two pistols on his side. His focus changed about finding the right time to fulfill his ambition of taking over the land for himself and then make it prosper.
- Warriors Orochi has a rather interesting take on Masamune. Chronologically, he's a steadfast ally of the Tokugawa, but the Orochi forces trampled the united force of Tokugawa-Date easily, casting doubts that Masamune was capable of uniting Japan, and thus surrenders himself to Orochi, becoming his Number Two, as he slowly felt some sort of kinship bond. He continued to act like he's worshipping Orochi while showing that the heroes, humans like them, were no better than him as they chose to prolong the war in the merged realm rather than being at peace, something even the heroes note about making a point. In 3, however, once Masamune realized that Orochi's incarnation, Hydra, no longer had the mindset of the Orochi he called friend and instead was a mindless monster bent on destruction (personification of his power), he just called it quits and then joined the good guys (which, when it was revealed that Orochi's consciousness went to Shuten Doji, who's a good guy, it makes Masamune's allegiance to Orochi seemed less evil as he seems to find kindship on his consciousness that would become Shuten Doji). In 4, he sticks to the good guys because of the memory reset.
- Sengoku Basara's version has attained infamy, wherein Masamune is a Gratuitous English-speaking Blood Knight who can wield six swords at once. He wants to take over the world and is The Rival of fellow poster boy Sanada Yukimura. And his horse is a motorbike.
Masamune: Are you ready guys?! Put ya guns on!
- This incarnation is famously voiced by Kazuya Nakai, who actually is also famous for voicing two characters/historical figure portrayls in the above franchise (Xiahou Dun and Dian Wei).
- The Basara version is so popular, that Miyagi prefecture (the area he used to control) used this image on posters encouraging people to vote in local elections.
- Samurai Deeper Kyo included Masamune who uses the nickname 'Bontenmaru' (historically his childhood name), and while a Boisterous Bruiser and ambitious, he remained as an ally of Kyo. Also he's voiced by Norio Wakamoto.
- In Sengoku Rance of the Rance Series, Masamune is a literal one-eyed demon that looks kinda like a Peeping Eye.
- While not appearing directly, in Persona 3, the main character's historical teacher Mr. Ono is an obvious Date Masamune fanboy. He teaches his class wearing Masamune's helmet (and probably eyepatch too) and thinks history lesson isn't cool until you get into the part about Masamune.
- Sengoku Otome give us a gender flipped version of Masamune. Who's actually Hideyoshi's teacher in the present day, Date-sensei its later revealed that Date Masamune is her ancestor and that she and Hideyoshi end up in a world where Date Masamune did not exist for some unknown reason.
- Date Seiji/Sage Date of Yoriden Samurai Troopers (Ronin Warriors) is explained to be a descendent of Date Masamune in supplementary materials.
- Total War: Shogun 2 has him as a special general for the Date Clan.
- Gate 7 gives us a grade student as the newest version of Date Masamune. And not just that; he's a yandere crazy jealous guy towards the main character, Hana, is a Bratty Half-Pint towards anybody else and tried to kill the poor Naïve Newcomer twice. But still, when he's in the battlefield, he's a hell of a good swordfighter.
- Masamune Date is mentioned in Yaiba: apparently he was the owner of the "Victory" Orb, required to discover the location of the legendary Orb of Ryuujin. He hid the orb in a small temple.... along with other 99999 fake ones.
- A Gender Flipped version appears in The Ambition of Oda Nobuna. She's a Large Ham Bratty Half-Pint here too. Given her youth, she's still going by Bontenmaru and thus the time-traveling Yoshiharu doesn't realize who she is at first.
- He's sort of the main character in Tono to Issho, where he's an idiotic Manchild with an eyepatch fetish.
- Another Gender Fliped version appears in Sengoku Collection, where she got involved with the Yakuza and is currently on the run from police.
- Masamune appears as one of the major warlords of Pokémon Conquest. He controls the nation of Avia and has a Braviary as his perfect link.
- The manga Neo Dragoon chronicles the life and times of Date Masamune alongside retainers like Katakura Kojuuro, Date Shigezane and Harada Munetoki. Also featuring Masamune's wife Megohime, here turned into an Action Girl.
- Team Fortress 2 references Masamune rather vaguely with a hat for the Demoman called the Samur-Eye, which looks exactly like most media depictions of Masamune's iconic helmet. The reference goes a bit further since the Demoman is also missing an eye (albeit the opposite one to Masamune and that it was lost to injury rather than Smallpox).
- He also appears as an old man in Shigurui, where he meets Tokugawa Tadanaga, Ieyasu's grandson.
- Masamune appears in Nioh for the Downloadable Content titled "Dragon Of The North", serving as the Big Bad. Accompanying him are Date Shigezane and Katakura Shigenaga, who's the second to bear the name Kojuro, the son of Kagetsuna (the usual bearer of the Kojuro title we see everywhere else), who died before the events began. Masamune had a HeelFace Turn after William beat him and revealed that he saved Shigezane while revealing Maria's manipulation on him; so in the next DLC (featuring Sanada Yukimura), he became an ally.