Yoshitsugu Ōtani

Yoshitsugu Ōtani is Yukimura's father in-law and Mitsunari's loyal friend who agreed to help him at Sekigahara. Though he was stricken by leprosy by the time the battle begins, he carries out his promise until his defeat. His son is Yoshikatsu. Historically, he was too frail to move by his own strength but this isn't true for his game appearances.

Before his playable Samurai Warriors appearance, he was a generic NPC since the first title. For the Samurai Warriors 4 character popularity poll, he placed second. The first character popularity poll for Sengoku Musou Shoot has him at sixth place. This counterpart has two character image songs titled Ryuu ~Kouun Ryuusui wo Koete~ and Mutsu no Chimata ni; he shares a duet with Takatora called Bunsuirei.

His Nobunaga's Ambition counterpart is fifteenth place in Gamecity's character popularity ranking for 2015.

In Saihai no Yukue, his height is 178 cm (5'10") and he is 27 years old. He likes to enjoy calm locations while gently warming himself in the sun, and his favorite food is salted konbu.

Samurai Warriors
The non-playable Yoshitsugu appears during some of the Toyotomi battles and at Sekigahara. During Kojirō's version of Osaka Castle, his son vows to avenge him.

His playable counterpart is a native of Oumi Province, so he first serves the local Azai clan. While reputed as one of Nagamasa's trusted retainers, Yoshitsugu mainly joined him because it was an obvious choice for him. He feels his lord's demise is imminent yet thinks he can learn something if he sees it in person. In the meantime, he enjoys scrutinizing Nagamasa's personality and mannerisms with his friend, Takatora. Both friends fight for the Azai at Kannonji Castle, Kanegasaki, Noda-Fukushima, and Anegawa.

When Nagamasa dies at Odani Castle, Yoshitsugu interprets a different lesson than his friend regarding their late lord. He learns the passion of defying "the flow of the era" for one's dream, no matter how futile the circumstances. Yoshitsugu respects Takatora's convictions, the friends choosing to part on good terms. Yoshitsugu wanders and finds servitude under Hideyoshi, the man he logically believes has the most momentum for claiming leadership. His relaxed composure annoys Mitsunari, causing the latter to nag him to act motivated at Bichu-Takamatsu Castle and Yamazaki. Yoshitsugu recognizes Sakon's talents from the latter battle and recruits him for Hideyoshi's cause at Shizugatake.

Kanbei suspects that Yoshitsugu's past with Takatora will be an obstruction to Hideyoshi's conquests, fueling suspicions of his betrayal when Takatora's invitation to desert is found before Komaki-Nagakute. Yoshitsugu claims his honest innocence of the letter. When the judgment committee sinks into silence, Mitsunari burns the letter to drop the accusations. Hideyoshi has no problem letting the issue slide, and Yoshitsugu is impressed by the young man's boldness. He believes he has found the one man with passionate dreams he can find himself supporting and dedicates himself to Mitsunari henceforth. The masked man fights for Mitsunari at Hiketa (Shikoku), Kyushu, Ōshū, Oshi Castle and Odawara Castle. He appreciates Takatora's warnings regarding the Toyotomi's fate in between these campaigns, accepting the reality that they will someday become enemies.

One month before Sekigahara takes place, Yoshitsugu had planned to take part in the subjugation of Aizu, away from the central conflict. He decides to pay a visit to Mitsunari's domain, Sawayama Castle, before departing. Yoshitsugu bluntly voices his pessimism for Mitsunari's plea and success yet agrees to join due to his earnest passion for the Toyotomi's dream. Regardless of the version, Yoshitsugu will always suspect Hideaki Kobayakawa and Hiroie Kikkawa of betrayal and will try to arrange for Yukinaga Konishi's rescue at Sekigahara.

His fate after either battle's iteration is the same: the Western army is overwhelmed and defeated. He dies in battle during the Eastern army scenario. In the pre-rendered version of his end, Yoshitsugu orders the last of his guard to fight for Mitsunari's escape. Takatora catches up to Yoshitsugu as he prepares himself for his honorable suicide, imploring his friend to realize his future under Ieyasu. Yoshitsugu declines, yet he fondly wishes for Takatora to keep living his vision. Once his words sink in, Yoshitsugu stabs himself and perishes when a pained Takatora acts as his second. His family's properties are detained by the Tokugawa after his death.

His 4-II focal story mentions his service to the Azai in passing as he starts as one of Hideyoshi's pages. He accompanies Mitsunari to deliver Hideyoshi's peace treaty to the Mōri. When Takakage threatens to take them hostage, Mitsunari dares him to try but lies about Yoshitsugu's service to protect him. His stunt convinces Takakage to agree, and the pages make haste to assist Hideyoshi at Yamazaki. Yoshitsugu frequently criticizes his friend's reckless clemency and blind faith in his ideals throughout his story, but he is grateful for his compassion.

Takatora greets him at Komaki-Nagakute, immediately suspecting Ieyasu to be a formidable foe to Hideyoshi. Mitsunari interrupts them to crassly inquire if Takatora is still holding a grudge against Hideyoshi for the Azai's fall, immediately souring any potential to befriend one another. Prior to Shikoku, Yoshitsugu agrees to act as a decoy for the main army. Mitsunari disregards the safety of the campaign to rescue him from peril. When Mitsunari is entrusted to his first chance at leading at Oshi Castle, he claims victory with his friend's help but suffers miserable losses in his campaign; he is unable to abandon his defense for the people and unable to define his objectives clearly. Reading his friends' expressions and well aware of Ieyasu's true potential, Yoshitsugu can't bring himself to completely condemn Mitsunari. He turns down Takatora's advice to abandon Mitsunari.

Feeling that he has been saved by Mitsunari more times than he can remember, Yoshitsugu resolves to fight at Sekigahara to return the favor. He directs the Western Army by altering Sakon's formation for the battle and claims victory. Ieyasu flees, and Yoshitsugu pursues at once with the intents of ending the threat against them. Mitsunari wants to rush to Yoshitsugu's aid, but tempers himself to remember his friend's wish to stay his ground and remember his status as a leader. His agonizing wait is rewarded with Yoshitsugu returning to him alive and well, but the screen quickly fades away, implying the ending might not be what it appears to be.

Warriors Orochi
He is a minor general who is often seen serving in any army with Mitsunari in this series. During the dream mode version of Xia Pi, he defends the pivotal water gate. If Mitsunari arrives to help him before the enemy officers heading towards it are defeated, he will say a special quote for his friend.

In Warriors Orochi 3, Yoshitsugu will be at Mitsunari's side during his service to the Wei army. In Ultimate, the Mirror Realm's Yoshitsugu deceives Hideyoshi and Nene at Shizugatake and lures them to a trap but is defeated.

Kessen
In Kessen, he is called "Otani" and acts as a low-keyed general for the Western army. He calmly asks his comrades to understand his friend's brash nature. In battle, Otani leads an archery or firearms unit with a small battalion of footmen to protect his men. He is one of the better and consistently loyal support units for players at Sekigahara. If the Toyotomi army consecutively wins their battles, Otani lives to see Ieyasu's end. Losing at any other part in the game will usually result in his death. Like Sakon, he may live past Mitsunari's death if their commander suddenly loses the battle at Edo.

He appears as an optional unit for Nobunaga's army in Kessen III. Yoshitsugu can join if the Oda army talks to the villagers and avoids killing innocents in their showdown with the Asakura. He is a ronin who has a good rifle proficiency and has good relations with Sakon; the two will perform better if they form a unit together.

Saihai no Yukue
Yoshitsugu is Mitsunari's best friend in Saihai no Yukue. A composed and quiet individual, he lost one of his eyes to his illness and is nearly blind. However, Mitsunari gave him the strength to live and he is willing to use the remainder of his life for his friend. He is a blunt and intelligent adviser for Mitsunari, often steering his friend away from brash and idiotic ideas. Since he says little about his own personal thoughts on the battle, some of the Western Army generals find it hard to trust Yoshitsugu. Though he will joke about his friend's abilities, he sincerely believes in Mitsunari and earnestly works to see their justice served.

When Kobayakawa betrays the Western Army, Yoshitsugu swears on his life to stop him. During this time, he advises his lord to focus on the defense with Konishi and Ukita. Though Mitsunari will save his friend from Kobayakawa, Yoshitsugu feels that his life is ending and requests to stay on the field. As his last wish, he asks his friend to not help him in his fight against Kobayakawa's reinforcements led by Tōdō. Surrounded by eight troops, he dies while lying against a tree and wishing the best for Mitsunari. After his death, Tamaki hands Mitsunari a letter he wrote, which tells his dispirited friend to stop being depressed and to never lose sight of his goal. Yoshitsugu's sacrifice and parting words continues to inspire Mitsunari's actions until the end of the game.

Development
Koinuma stated that he originally had no plans to include Yoshitsugu due to his severely limited role for the era. He changed his mind when the figure topped online fan surveys for most wanted playable Samurai Warriors character. Yoshitsugu's service under the Azai was done in an attempt to expand his character appearance and importance. He was visually designed to be "mysterious and skilled yet frail" to contrast other intellectual characters. He was originally associated with the butterfly during his attacks, but developers realized this was too similar to Nō's image midway into development and changed it to the mayfly. The change follows with his design theme and doubles as a homage to his code of arms. Yoshitsugu's overall design motif was inspired by his iconic exploits at Sekigahara for simple recognition. While they do not show it, the designers add that his face is "extremely good-looking".

Personality
Broad-minded Yoshitsugu is an analytical youth. In the blink of an eye, he can accurately pinpoint a person's motivations and identify the logical advantages and fallacies of every strategy. He expects everything, rarely surprised by sudden betrayals or ambushes. He never questions the morality of death or the wars. For the majority of his life, Yoshitsugu favors the rational and never thought to challenge the inevitable, or "the flow" of events around him. During this time, he indulges his thoughtful meanderings with the like-minded Takatora. Yet the vigor people display in their futile fights against fate intrigues him to reconsider. Once he embraces his own change of heart, Yoshitsugu enjoys the paradox of following a path he knows dooms him.

While he may seem sober and staid, his heart can be swayed by compassion and sympathy. He feels Mitsunari is an irrational mess who is trying too hard to impress. The strategist makes no attempts to hide his criticisms for Mitsunari's brash impulsiveness yet Yoshitsugu can't bring himself to ignore the youth's kindness and concern towards him. His friend's devout exertions for the Toyotomi inspires the strategist to join him. Since they regard Mitsunari in a similar light, Yoshitsugu bonds with Sakon. Both men want to do their best to defend Mitsunari's sentimentality.

Yoshitsugu can also be a straight-faced comedian, especially in his personal events. Every now and then, he will stoically fib to exploit Mitsunari's unbridled trust in him. He takes jabs at Takatora's snack obsession and tough front. He suckers the protagonist to believe he is in love with him/her by purposely rewording his/her affections for him. He is aware that he is slandered as "a ghost" due to his apparent listlessness and pale attire. Rather than deny or deride the accusation, Yoshitsugu plays the part with complete seriousness. The strategist is hearten when Masanori is naive enough to fall for the act and mangles Kiyomasa's heavy-handed retorts to work for his role's vengefulness. Despite his teasing, his jokes are not mean-spirited as he sincerely treasures his friendships.

Character Symbolism
In the Samurai Warriors series, he is symbolized by the kanji for "flow" (流) and "emotion" (情).

His default weapon is partially named after the color vermilion. Following in the footsteps of medieval Chinese thought, the color represents someone who is easily manipulated in medieval Japan. Fu Xuan is the earliest known writer to be credited with the color association and is the one who wrote the Chinese proverb, "He who stays near vermilion gets stained red; he who stays near ink gets stained black." It metaphorically means that a person's habits or mannerisms may be influenced by the people around them. Within the context of the original proverb, it's a warning to keep good friends. The old Japanese idiom, "You'll turn vermilion", is a shorter version of it. Yoshitsugu's weapon reverses the normal spelling for saihai to imply that the "vermilion" is controlling him.

Kukunochi, an obscure Japanese deity, forms the namesake of his rare weapon. Furukoto Fumi describes that he is one of many created by Izanagi and Izanami during their creation of Japan. His name is often spelled with the archaic characters for bark or tree, so he is thought to be a deity for either one. In Shintoism, he is often deigned the polar Wood deity. Kukunochi is one of the middle children between the deities mentioned in Takatora's and Mitsunari's rare weapons.

The likely namesake for his DLC weapon is an alternative name for Amenonuhoko, Amanomagaeshinohoko. The secondary name for the pike invokes a stronger imagery of defiance against Heaven's design rather than a broad opposition of it.

Yoshitsugu's heirloom references stories of his appearance at Sekigahara. He was blind and was so crippled by illness that he could not stand or don armor. Even so, Yoshitsugu sought to present himself as a proper general. He wrote "paper armor" onto a piece of paper and wore it over his body. His men were greatly moved by his integrity to duty and repaid him by driving the Eastern army at bay. During the early movements of the battle, the Ōtani forces were one of the armies reputed for their ferocity.

Voice Actors

 * Brooke Burgess - Kessen (English)
 * Sascha von Zambelly - Sengoku Musou TV series (German)
 * Satoshi Hino - Samurai Warriors 4
 * Kouji Haramaki - Warriors Orochi series (Japanese)
 * Kaneto Shiozawa - Kessen (Japanese)

Live Action Performer

 * Masanari Wada - Butai Sengoku Musou Sekigahara no Shou, Butai Sengoku Musou Shikoku Ensei no Shou
 * Shota Yamanaka - Butai Nobunyaga no Yabou ~ Neko Gungi

Quotes

 * See also: Yoshitsugu Ōtani/Quotes


 * "First time out and I'm second place... Everyone who voted for me must be hopeless. Still, if the public favors me here, then perhaps I shall try to be below third place next time."
 * "My goal now is to win with you, King Kamehameha."
 * "Great job taking care of Katsuie for me. You were beautiful out there!"
 * "I am not worthy of your praise. Not even the heavens can top the joy I feel now."
 * "When we head towards Chugoku, it's great knowing I have someone I can really count on. Why, I want to see you lead 1,000,000 men right now!"
 * "As long as it pleases you, my lord, my power is always yours to command."
 * Hideyoshi and Yoshitsugu; 100man-nin no Sengoku Musou


 * "Lord Otani, what is it that inspires you to have such faith in the man?"
 * "Mitsunari and I have bonds built of time."
 * "Out of obligation?!"
 * Shimazu and Otani; Kessen


 * "Yoshitsugu, do you think we can claim victory somehow?"
 * "Mitsunari, it is not about the possibility of winning. Victory is infallible. As the army's commander, you should be the one believing this the most."
 * Mitsunari and Yoshitsugu; Saihai no Yukue

Charge Moveset

 * , undefined, (undefined): Strikes upward followed by a small quake on the ground cause with his baton slamming down.
 * ,, undefined, (undefined): Blasts a ball of bright-lightning that stuns, and extra inputs cause lightning bolts to fall from the sky, then rains some lightning bolts around Yoshitsugu himself after a few gesturing signals.
 * ,, , undefined, (undefined): Unleashes a whirlwind in front of himself with the baton's blade in a rushing turn to the right, before slashing along the ground upward with his staff's bladed-end, sending forward a vertical air wave.
 * ,, , , undefined: Sends out some dragonflies that expand to the area in front of him and explode.
 * ,, , , , , , : Strikes three times (inward, outward, inward), then slashes four times with the extended baton's blade (via up and down on the same diagonal-line) and finishes with a small exploding ball of energy forward from his free palm, which causes a crumple on hit.

Hyper Moveset

 * undefined: Quickly slides forward while striking with the extended staff via the sharp-shaft-end. Slashes to the left from the right on the first input.
 * undefined, : Jumps and strikes to the ground, creating a small quake.
 * undefined, undefined, : Shoots a purple ball of energy akin to his C3.
 * undefined, undefined, undefined, : Shoots a half-circle-spread of energy beams around.
 * undefined, undefined, undefined, undefined, : Leaps forward and releases sharp winds to cut enemies.
 * undefined, undefined, undefined, undefined, undefined, : Drags his blade along the ground while sending forward a vertical air wave akin to his C4 finisher.
 * undefined, undefined, undefined, undefined, undefined, undefined, : Releases a volley of dragonflies that fly forward and explode.
 * undefined, undefined, undefined, undefined, undefined, undefined, undefined, : Same as his Hyper C6.
 * undefined, undefined, undefined, undefined, undefined, undefined, undefined, undefined: Repeatedly lunges forward, striking with the extended staff.
 * , : Slashes outward with his baton's blade to the ground.
 * , undefined: Fires down an orb to cause an OTG-hitting quake in front of him. One of the few jumping charge attacks to not be physical-based and does not center on the user's falling position.
 * Slashes forward from left to right in a zig-zag formation with the extended staff. The finisher involves him jumping into the air and releasing a stream of exploding charms onto the ground.
 * (Ultimate/Kaiden): Summons wads of dragonflies that drop exploding charms in front of him.
 * Rage Attack/Musou Gokui effect: Powers up his attacks with the wind element.


 * Spirit Cancel:
 * Deadlock Attack & Mighty Strike: Slashes twice akin to his 4th-to-7th normal attack inputs, then thrusts his baton's tassel-end at his target's face.
 * R1: Conjures multiple balls of energy to slowly float in front of him as they descend to the ground at a slow speed. Explodes upon contact which knocks back foes.
 * Awakened Skill effect (4-II only):

Mounted Moveset

 * , undefined: Strikes forward.
 * ,, undefined: Skewers enemies with the sharp end of the staff.
 * ,, , undefined: Releases a small purple ball of energy onto the ground.
 * ,, , , , , , : Strikes repeatedly to the right and finishes with a slash with the sharp end.

Fighting Style
Yoshitsugu uses a baton with a hidden blade on its opposite side, focusing on simple waving smacks followed by occasional usage of the said hidden blade to skillfully slash at enemies (creating vertical shockwaves and brief flashes in the form of whirlwinds). He also literally throws in magical-based attacks such as exploding talismans, energy orbs, lightning storms (something Mitsunari also shares), energy beams and summoning dragonflies to storm his targets.

As a Hyper-based moveset fighter, Yoshitsugu's Hyper Attacks have great clearing, but are hard to aim. His normal attacks are solid, but at a cost, his normal base string moves him forward rather poorly (but makes up for it with good coverage and decent damage).

Weapons

 * ''See also Yoshitsugu Ōtani/Weapons

Rare Weapon Acquisition

 * Stage: Second Siege of Ueda - The Search for Gracia

Personal Info
Ōtani Yoshitsugu has been romanticized in poetry and fiction as Ishida Mitsunari's heroic and talented friend since the Edo Period. It is said they have been good friends since their early days working with Toyotomi Hideyoshi, each respecting the others' judgment and character. A particularly famous episode between them occurred during a tea ceremony at Osaka Castle in 1587. An ill Yoshitsugu drank from the tea bowl traditionally passed among the attendees but left an embarrassing spot of pus after his mouthful. Keeping true to the ceremony, he was forced to pass it on to others. The attendees shied away from their traditional gulp and respectfully moved it along the line. When it came to Mitsunari, he drank the entire contents without faltering and commented that the tea was superbly delicious. Yoshitsugu was touched by his friend's gesture, commonly said to have led to his determination to fight for the Western army. There is also a legend of the two being romantically involved with one another due to their close ties, sometimes argued to have started due to this event.

While the tea ceremony incident was recorded by people actually alive during the time period (Kamiya Sōtan and Tsuda Sōgyū being among them), the subject of their actual friendship is under speculation. To be more precise, Yoshitsugu himself is put under eye of skepticism. Stories from the Edo Period will appraise Yoshitsugu as an honorable and talented retainer since his youth, but nothing in historical records offers details to support their claims. His father is said to either have been Ōtani Yoshifusa (retainer to Hideyoshi) or Ōtani Moriharu (a vassal of the Ōtomo family) since they both shared the same family name. Both men are of unknown origin and have little recorded for them beside a few notes and their names. It is often said that he was born in Ōmi Province; his mother was one of Kōdai-In's maids and was how Yoshitsugu became favored by Hideyoshi. However, if one is to believe his father was Moriharu, this defenestrates the story entirely since Yoshitsugu was also said to have only joined Hideyoshi after departing from the Ōtomo family in his late twenties. Since little is known about either Ōtani clans to completely verify the stories, Yoshitsugu's first meeting with the Taikō is a mystery.

The unknown sections of his life creates a twenty or thirty year gap often filled with stories and rumors. Among those put into question is his bonds with Mitsunari, since legends will proclaim they knew each other since they were serving under Hideyoshi in their youth. Stories commonly state Yoshitsugu was only a year older than Mitsunari, but speculation has been arising that he was actually much older or younger than his friend due to the mixed accounts of his roots. His age is at odds with the tales created for their relationship -romanticized to have occurred due to their close ages- and adds more mystery to Yoshitsugu. The contradictions have been so confusing that a rather radical theory has been emerging with a small portion of believers for their friendship. This story argues Yoshitsugu had died of his illness within a year of contracting it and that the Yoshitsugu at Sekigahara was actually a heavily ailed Hideyoshi in disguise. While an interesting concept, it needs to prove Hideyoshi had somehow survived his historically accepted death date and adds more fuel to the debate. In any case, speculation over whether the two men truly considered one another friends continues to this day.

He is not accredited with an official wife, but he supposedly fathered three sons and one daughter. His second son died with him at Sekigahara while his other two argued male offspring either fell with the Toyotomi family at Osaka Castle or lived past the wars in seclusion. Yoshitsugu's daughter was Sanada Nobushige's first wife. A purposed folktale states Yoshitsugu had one concubine prior to Sekigahara, who went insane with grief after his death. While it's unknown if the claim holds any merit, Tsuda Sutezō of the Byakkotai was rumored to have been one of his descendants.

Other Names
In the event that Yoshitsugu was born under Yoshifusa, there is a popular story regarding the origin of his childhood name, Keimastu (桂松 or 慶松). Before his son was born, Yoshifusa lamented his luck with children and wished for a male heir. One day, his wife decided to pray before a shrine dedicated to Hachiman Daibosetsu in their land. As she uttered her desires for a boy, a pine tree was cut before the shrine and fell before her. She plucked a portion of the fallen branches and ate it for good luck. When she gave birth, Yoshifusa was happy to see his first son. Grateful for the god's answer, he named his child after the plant.

His first legal alias was Heima (平馬), which was given to him during his early services with Hideyoshi. He was either given this name for his leadership of the cavalry at Harima or in recognition of his service at Miki Castle. A few years later, temple printings associate him with having the alias Kinosuke or Norinosuke (紀之介). He has also been argued to had his name changed to either Ōtani Gyōbu (大谷刑部) or Ōtani Yoshitaka (大谷吉隆). Gyōbu reportedly was given as a respectful link to the Genji family or in honor of Yoshitsugu's higher rank at the time. Yoshitaka was either his actual given name in history or an alternative nickname.

When Yoshitsugu fell ill with leprosy, he was popularly described to have looked dreadfully pale, which led to his nickname "White Face" (白頭). Legends state the name may have been also caused since he covered his face with a white mask, a typical attire when stricken with the disease.

Serving Hideyoshi
Coming from unknown beginnings, Yoshitsugu could have entered Hideyoshi's services as a low rank kōshō or became Mitsunari's yoriki in the mid or late 1570s (either in his mid teens or mid-late twenties). Several stories will state that his intellect and charm had earned him many friends, but the legitimacy of the claims are still debated. His early achievements with the Hashiba family are not known, but most sources argue that he was among the 700 or so named individuals who sided with Hideyoshi after the Incident at Honnōji. He joined Katō Toranosuke, Fukushima Ichimatsu and other kōshō to take Nagahama Castle away from Shibata Katsutoyo, Shibata Katsuie's nephew. Hideyoshi has been romanticized to have said the following for Yoshitsugu at this time, "Give me a million troops and I would love to see him guide them."

Once the Battle of Shizugatake commenced, Yoshitsugu was said to have took part within the Toyotomi ranks. What he did -if anything- is scattered amongst legends and folklore. One account states that he was the one who used his wits to convince Katsutoyo to surrender prior to the battle. Yet another tale will depict him as a brave warrior in the front lines, who performed many deeds with his magnificent spear. The Hitosuyanagi Kaki is famous for stating that Hideyoshi offered immense praise to both Yoshitsugu and Mitsunari for the battle, stating particularly for Yoshitsugu, "Ōtani Keimatsu was the participant who was excellent since the first move." However, this statement does not appear in other historical texts, so it's possible the quote is entirely fictional.

What is known for sure about Yoshitsugu's service was that he was named Gyōbu-shōyū (a minor Minister of Justice) in 1585. By then, Yoshitsugu was said to have been accepted as one of the elites within Hideyoshi's inner circle. According to the Uno Mondo Nikki, a document written as secretary records for Kennyo, Yoshitsugu and Mitsunari were among the men who accompanied Hideyoshi to Arima Onsen in September the same year and soaked in the same pool as him.

During this time, Yoshitsugu has been said to have become ill with a serious disease. There is a particularly famous tale as to why he could have been inflicted with any ailment. In 1586, as he stayed within Osaka, a riot ensued and Yoshitsugu went to quell it personally. He slew 1,000 men to Hideyoshi's pleasure, but the gore had splattered within his internals and infected him. The Uno Mondo Nikki and Tamon-In Nikki, which is said to be the diary of the monk Eishūn, state a milder version of Yoshitsugu being ill. They report rumors of Yoshitsugu searching to receive blood from living beings within the city, a method that was believed to have cured diseases. It has also been said that he was actually sick since Shizugatake, but his symptoms did not become apparent until this time. His illness was not described in detail within historical records, yet people generally believe that he was inflicted with leprosy -due to tales from the Edo Period- or syphilis -alternate explanation due to the involvement of bodily fluids.

From here, Yoshitsugu's history is split into two major accounts. The Saifuku-ji Enkinsei, a supposed historical text which is currently being critically analyzed for its authenticity, claims Yoshitsugu went with Mitsunari to Kyushu in 1587 and helped him lead 12,000 troops without any major difficulties. In 1588, Mōri Terumoto's diary states Mitsunari was escorted by three other individuals who were known to give him frequent consul. Although no names besides Mitsunari are given in his description, people like to insert Yoshitsugu as one of those men present. As a reward, Yoshitsugu was given 50,000 koku and became the lord of Tsuruga Castle. Becoming the local magistrate, he divided 10,000 koku amongst the territory of the Toyotomi vassals within his region. He went with Mitsunari to Odawara Castle and was said to have also been present at Oshi Castle, though details of his activities for both conflicts are not clearly listed. When Hideyoshi ordered another suppression of Kii Province, Yoshitsugu was one of the men who participated and caused Akita Sanesue's defeat. He has also been accredited to following Mitsunari through various riots, was a part of creating Fushimi Castle as a fort, and took part in the Korean Campaign. Within the latter conflict, the reputation for his navy was said to be the unparalleled gem of the seas.

Yoshitsugu returned as a celebrated hero from Korea and was welcomed by Hideyoshi within Osaka Castle. He was invited to share tea with Hideyoshi at a banquet. As the festivities between the two lengthen, Yoshitsugu's nasal mucus accidentally leaked into his tea bowl. Yoshitsugu was about to leave in embarrassment until Hideyoshi noticed him. Expressing that his throat was parched, he asked Yoshitsugu to hand him the same tea bowl with the snot. When it was given to him, Hideyoshi stated that the liquid would be exquisite from his vassal's capable hands and drank it as though nothing were wrong with it. Crying for the first time in his adult life, Yoshitsugu henceforth swore loyalty to the Toyotomi family in gratitude.

The not-as-popular yet reasonable secondary account depicts Yoshitsugu bedridden by his illness. The Rokuon-In Chiroku, said to be the diary of the head monk of Kinkaku-ji during this period, states his illness had advanced into its serious stages and Yoshitsugu had not left the immediate area of his residence in five or six years. His body was unable to endure hard travel, meaning that he couldn't sail overseas or take part in heavy campaigns. In spite of what the former account states, he did not attend in the post Korean Campaign festivities, such as the Daigo Flower Viewing, due to his weakened state. He has been reported to have left his home once in 1598 to celebrate Hideyori's introduction to the court and was given snacks for his illness by a frail Hideyoshi.

Sekigahara
Following Hideyoshi's death, Yoshitsugu planned to ally himself with Tokugawa Ieyasu in the Ietada Nikki. In 1599, Yoshitsugu gathered his men and moved with the Tokugawa troops as far as Tarui Castle. According to the Keicho Kenmonshu, Mitsunari was at Sawayama Castle and invited Yoshitsugu to his realm. Though blind due to his illness as he entered the gates, Yoshitsugu was appalled to find armed soldiers awaiting him and developed a silent grudge toward Mitsunari. Undeterred, Mitsunari introduced him to his vassal, Shima Kiyooki. Kiyooki flipped Yoshitsugu's perceptions of the Western army, but he wanted to remain within Ieyasu's ranks as he believed Mitsunari could not win. However, for one reason or another, Mitsunari was able to convince Yoshitsugu to defect and join the Western army. A legend states that Ieyasu was aware of Yoshitsugu's talents and was prepared to offer 12,000 koku to have his services. Hearing Yoshitsugu's sudden change of allegiance genuinely surprised him.

As for why Yoshitsugu changed his mind, the reasons remain an enigma to this day. No one really knows why Yoshitsugu did it since little is recorded for it. There are many tales made for why he could have, but they lack any real backing due to the absence of historical evidence. Of course, the popular scenario was developed during the Edo Period, stating he joined out of friendship. In this interpretation, Yoshitsugu was only thinking of joining Ieyasu and was asked three times by Mitsunari to join him. Although Yoshitsugu knew it was a failing cause, he couldn't abandon his ties for his friend and merged his forces into the Western army with his sons. Yet another story states Sanada Masayuki's wife was being held hostage by the Western army. Tied to the Sanada family due to his daughter's marriage, he was forced into the hands of the opposition for her safety. Another fable depicts that he conflicted with Ukita Hideie and was joining Ieyasu just to avoid him. Mitsunari heard of this and played mediator between the two parties, eventually convincing Yoshitsugu to stay.

Whatever the reason, Yoshitsugu fought for the Toyotomi family thenceforth. He was rumored to have misinformed Maeda Toshinaga of the dangers of Asainawate, leading to the battle with the defending Niwa Nagashige (this has been speculated to also be another falsehood tied with him however). His other activities before the Battle of Sekigahara are not clearly known, but he was said to have suggested Mitsunari to relocate his main base the night before the conflict. Yoshitsugu commanded an army of 600 for the battle. He had three other subordinates under his command: Hitatsuka Tamehiro with 900 troops, his son, Yoshikatsu, with approximately 2,500, and Kinoshita Yoritsugu with 1,000. According to the Sekigahara Gunki Taisei, Yoshitsugu was aware of Kobayakawa Hideaki's plans for treason yet was powerless to stop it from happening. Repositioning his army to keep an eye on Kobayakawa's movements, he allegedly did so as he did not want his allies to suffer too much from the predicted betrayal.

Once the Kobayakawa army of 15,000 charged down the mountain towards the West, Yoshitsugu's army stood as the shield to their advance. Armed with a capable army of elites, it would seem that Yoshitsugu had the upper hand for the first clash (the Kobyakawa army had 370 dead or wounded while the Ōtani suffered 180 or so losses). However, Tōdō Takatora's army lashed at Yoshitsugu's flank. The Ietada Nikki records Kiyooki's fourth son, Shima Kiyomasa, within Yoshitsugu's ranks and he tried to kill Takatora in one blow. However, Kiyomasa was struck down and killed by an Eastern general named Takagi Heizaburō. Kiyomasa's fate echoed the situation of the Ōtani flanks as their defenses crippled from all sides due to the overwhelming numbers. Utterly defeated, Yoshitsugu lost his ground and is said to have committed suicide. Assuming that he was known as Yoshitaka, a grave marker was placed for him at Sekigahara.

There are two famous accounts of his final moments, though they are both deemed questionable in their authenticity. In the Keicho Nenjuki, Yoshitsugu was not able to move of his own power and gave his orders to his subordinates through a palanquin. As the battle with Kobayakawa continued, he instructed his nearby retainer, Yuasa Gosuke, to inform him when the battle was lost. Many times did the cries for defeat echo throughout Yoshitsugu's camp, yet Gosuke continued to insist that the tides could still change. Once Gosuke admitted they were headed for defeat, Yoshitsugu popped his body half way out of his vehicle and sliced off his own head. Gosuke had promised his lord earlier that he would hide his lord's head so it would not be discovered by the enemy, yet he died in battle while attempting to flee from Takatora's army. The same book also reasons that Yoshitsugu had propped himself on horseback and ordered to be sliced at his torso once Gosuke gave the word.

The other story has its roots during the mountain of folklore developed in the Edo Period. Tamehiro was the one to report back with the ill news to Yoshitsugu and was sorely regretful for not being able to stop Kobayakawa. In his remorse, he sang a poem to encourage his lord to commit suicide, which is roughly translated as, "That I might abandon thy life for thy name, to meet thy sudden end of the world so ruefully." Yoshitsugu appreciated the loyalty behind Tamehiro's words and replied with his own poem, "May we pledge to the Six Paths, and wait for but awhile, to reunite once again on the life ahead." As his reply was sent, Tamehiro did not get to read it as he had already been killed by Kobayakawa soldiers. Turning to Gosuke when ready for his own death, Yoshitsugu asked his retainer to assist him and to hide his head from their enemy. Whilst still in his palanquin, Yoshitsugu stabbed his stomach into a cross spear and his head was chopped off by Gosuke. Gosuke was said to have ordered for his lord's head to be buried in secret before rushing to his own death against the Eastern army. A radical variation of Gosuke protecting Yoshitsugu's head from detection is also known; in this version, he decapitates himself to divert attention to his master's remains. The Eastern army mistook Gosuke's head as Yoshitsugu's and it has been said that the real one has yet to be found.

Regardless of whether he was a hero or not, Yoshitsugu continues to be celebrated for his samurai spirit and loyalty to his duties. His tragic end against monstrous odds is one of the many popular tales of Sekigahara.

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