Carving up faces and balls as a katana-wielding 16th-century samurai warlord is probably one of the most badass things human beings have ever done. There's just something inherently fucking cool about dudes in big scary plate armor slicing off joints with razor-sharp swords, screaming through a field of battle knee-deep in the blood of their fallen enemies. In light of all this, no man fully exemplifies the full spectrum of hardcore awesome samurai shit quite like the unmatchable Date Masamune – a mighty, almost-legendary swordsman and general who fought his first battle at fifteen, was never defeated in single combat with the enemy, wore an eyepatch made from the hilt of a samurai sword, and was so over-the-top Money Mayweather swanky that his name is still used as an synonym for "big pimpin’" in Japan to this very day.
Date Masamune was born in 1566 in the northern part of Japan. He was the scion of the Date Clan, a powerful, wealthy family known for its ability to trample the balls of its enemies into ball-dust and embed massive swords into the skulls of anyone dumb enough to piss them off. Blooded for combat and responsibility and badass shit as a ridiculously young man, Date wore an eyepatch at 12, was married at 13, and won his first battle at 14, cutting his way through a rival clan with a sword in each hand and an insatiable blood rage in his guts. By the time he was 17, Date's father stepped down as Clan Leader and put Masamune in charge, sending the teenager out to command rampaging field armies of hardcore samurai and earn glory and honor for his family.
This about this for a second -- If Date Masamune had been alive in 2014 he wouldn't have been old enough to buy porn. In 1583, he was wearing an eyepatch, hooking up with wives and concubines, and ordering thousands of samurai to destroy the enemy without mercy and immediately decapitate any enemy soldier dishonorable enough to surrender.
Now during this period of Japanese history – a region descriptively-known as The Time of Warring States – there was technically a shogun and an emperor and all that stuff, but neither of those guys really gave a shit if all the little samurai clans went around wiping each other out and stealing each other’s’ land and shit. Basically, if you had an army of spearmen, a solid suit of samurai armor, and a pair of trusty tempered-steel blades, you could carve your way up and down the countryside and nobody would really fuck with you. And that's exactly what Date Masamune planned to do.
As head of Date Clan, Masamune was, first and foremost, a master of gaining territory through cleverness and intelligence. Focusing primarily on diplomacy, sabotage, and bribery, Date used badass spies, fucking ninjas (!), and giant gold-laden treasure chests to gain territory wherever possible, but if that didn't work he also didn’t mind ramming a katana through your eye socket and impaling your head to a post. One way or another he was going to sleep in your bed, eat your steaks, and bone your concubines -- you could just do it the easy way or the hard way. This sort of mentality brought Date in conflict with a rival clan known as the Ashina, a group of people who pissed Date off when they gave one of Date’s men a bunch of gold to betray him and then let that asshole hang out in their castle rather than hand him over to Date for summary execution. Enraged, Masamune attacked at the head of an army of face-slicing samurai, cleaved through the Ashina with extreme violence, sacked their castle, killed 800 people (including the traitor), and scared the soldiers of a nearby Ashina fortress so shitless that they burned their own fort and ran for it in a desperate attempt to avoid the wrath of Masasume (it didn’t work).
Growing his might to become a powerful regional warlord, Date continued to expand his power base one plundered village at a time. It was a policy that pissed off another rival clan, the Hatakeyama, mostly because it was their castles and towns being infiltrated by ninjas and burned down by samurai horsemen. The Hatakeyama Clan leader, a ten-ton jerkass turdburger named Hatakeyama Yoshitsugo, decided that the best way to chill Masamune out was to kidnap his father at sword-point and hold him for ransom, which, if you've been paying attention, really wasn't a very good plan. When Date heard the news that his dad had been captured, he got understandably pissed-as-fuck, rode out with an army, and caught Hatakeyama on the shores of some river somewhere. Hatakeyama held up Date’s dad as a human shield, threatening to kill him if Date got any closer, but instead of backing down like a punk Date Masamune instead called up a line of badass armor-wearing musketeer riflemen and ordered them to load their guns.
When Date Masamune hesitated to give the order for his men to fire, Date’s dad – still being held as a shield by Hatakeyama – angrily screamed for his son to man up and give the order. That’s how tough this clan was – their former leader was ballsy enough to say, “Fuck this guy, I’d be happy to take a bullet if it means killing him.”
Unfortunately, Date still hesitated (and who can blame him?), and Hatakeyama quickly panicked, lost his shit, and cut Date’s father’s throat. Date gave the order to fire, but it was too late -- Hatakeyama ran for it, somehow eluding the fusillade of gunfire that followed him.
Date Masamune learned an important lesson that day. The kind Bruce Willis learned from one of those terrorists in Die Hard: The next time you have the chance to kill someone, don’t hesitate.
Date Masamune amassed his army, destroyed Hatakeyama’s army on the battlefield, raided his castle, burned it to the ground, and tortured and killed that asshole and his entire family. Hatakeyama’s severed head was on display in Date’s castle for weeks. Just to tie off loose ends a few years later Masamune went back to war with the Ashina, bribed some of their best commanders to betray them at the height of a critical battle, and beat their asses so hard that Ashina samurai were jumping into a river and drowning just to escape the mad slaughter-tastic rampage of Date Masamune and his men.
Known as “The One-Eyed Dragon,” Masamune lost his right eye to smallpox at an early age. The story goes that the infection messed Date’s eye up so bad that it fell out of its socket and just hung there, so Date plucked it out with his bare hands because he thought it would be a liability in combat to have his eye hanging off his head. I don’t know if that’s true or not.
Date Masamune never lost a campaign, was never beaten in one-on-one sword combat throughout his extensively-long career as a samurai warrior, was really good at arm-wrestling, and could drink any idiot under the table. He built his Clan into a mighty swath of territory that covered almost the entire northern third of Japan, ruling from his capital in Sendai, a city that at this time was even more prosperous than Tokyo and was home to tons of gold mines and lucrative shipping ports. He mostly used these to trade the Europeans for things like guns, bullets, and more guns.
Known for putting elaborate long, curved, gold-plated crescent moons on his helmets and marching his men in badass black armor with gold trim, the sight of Date Masamune’s army was so impressive that it inspired the word Datetoko, which basically means “big pimpin’” in Japanese. The phrase is still in use today.
Of course, in true badass fashion, Date Masamune not only dressed his guys in the most fanciest, expensive armor of any daimyo in Japan, but he also was the only guy to make sure that his army was ultra-heavy and capable of deflecting fucking gunfire from old-school arquebuses.
Despite being refined, ruling the third-largest fiefdom in Japan, and living a life of wealth and excess full of huge parties, massive palaces, and tons of hot chicks, Date Masamune was also a stone-cold warrior who led from the front, could call forth unbelievable numbers of warriors at a moment’s notice, and hated any kind of weakness or wussiness. Like one time he was drinking some kind of fancy expensive tea out of an unbelievably-expensive gold and porcelain cup. As he was about to kick it on a couch surrounded by babes and sip his tea, the cup slipped out of his hand. Date was like, “oh crap!”, but then he used his lightning-reflexes to snatched the cup out of the air before it hit the ground. The second he grabbed it, Masamune instantly became super pissed-off furious-as-fuck by the fact that he could stand bravely on the battlefield and stare death in the face without flinching, but that the thought of accidentally cracking one stupid dainty tea cup caused him to display an emotional outburst that resembled something other than pure, unadulterated blood rage. Thinking about this made Masamune so mad that he slammed the mug into the ground, shattering it into thousands of porcelain shards.
Here’s another good example of this sort of thing – while leading his troops in the siege of Osaka Castle, Date Masamune decided that his front-line ashigaru peasant warriors were half-assing their asskickings and weren’t fighting as hard as they could. So he ordered his riflemen to move up and fire two volleys at the backs of their own men to motivate them to fight harder.
This isn’t a guy you wanted to fuck with.
By 1590, Date Masamune and Toyotomi Hideyoshi were the only two daimyo left standing in Japan. Toyotomi had consolidated the lower 2/3 of Japan into one big empire, and by the time that guy came around, Date knew that Toyotomi was much too powerful to take on in battle. But rather than submit, Date handled it in the manliest way possible: He was like, “Yeah, you're tough, but so am I. So fuck it, let’s just chill, combine our powers, and be buddies.” He agreed to serve as a vassal to Toyotomi as long as Toyotomi didn’t get all up in his shit and start telling him what to do. Toyotomi became shogun of Japan, and Date Masamune led armies in both of Toyotomi’s invasions of Korea in the 1590s as a show of support to the Emperor and the shogun. When Toyotomi bit it, Date became a retainer of the next shogun, a guy named Tokugawa Ieyasu, and helped Tokugawa win the biggest battle in Japanese history, the Battle of Sekigahara, in 1600 AD.
Here’s a crazy story: Date Masamune once gave a pair of samurai swords to the Pope. I’m not kidding.
Date had converted to Catholicism a few years before 1613, agreeing to convert after watching a Catholic missionary cure one of Date’s girlfriends of some horrible illness. So in 1613, Masamune decided he wanted to set up a trade route with Europe, and he built a western-style sailing ship and sent a delegation of Japanese nobles to Europe with a letter for the Pope and a couple ceremonial katana swords. His men sailed to Acapulco, Mexico, crossed over land to the Atlantic, picked up another ship, and became the first Japanese to cross the Atlantic Ocean. They landed at Madrid, met King Philip III of Spain, then went around to Rome and delivered the message to Pope Paul V. Then they came back.
The entire trip took seven years, kind of like the original mission of the USS Enterprise. Date’s men triumphantly returned with permission from the Pope to build a Catholic mission on Date lands, but unfortunately for those guys the Shogun had banned Christianity while they were out of town. Ah well.
In terms of badass samurai, Date Masamune was one of the all-time greats. It started with plucking out his eye and killing a man at age 14, but this ultimate badass stomped gonads in combat for over fifty years, finally passing away in 1636 at the age of 69. He head come into feudal Japan as the first-born son of a moderately-regarded Clan. Through steel, guns, espionage and ninja shit he took over a third of the country, became one of the most powerful rulers of his era, and played a vital role in the rise of two warlord shoguns. He led sword-swinging warriors into battle in two of the most important battles in Japanese history, did two tours of duty in Korea, commissioned a badass voyage that spanned the entire length of the globe and gave swords to the pope, and killed countless men in combat without ever losing a campaign.
By the time he finally left this earth, he had seen the end of the Warring States period of Japanese history and the beginning of a period of peace that would last for over two hundred years.