Randomly rambling my interpretation of Date Masamune’s characterization.
Last night I was browsing some old DateSana fan-art from Xiaotakara. (I'm still sad he left Tumblr! ;o;!) And his confident seme portrayal of Masamune was a stark contrast to the more vulnerable "switch" Masamune that I had been seeing in the fandom lately. I had always thought that this discrepancy was caused by the difference between Samurai Kings Masamune and Judge End/videogames Masamune, because frankly, that had been my experience. Despite there being so many portrayals of Masamune, besides the typical dominant seme, and I do enjoy him being secure in himself enough to be a "switch", I just can't fully accept the vulnerable/insecure Masamunes and dorky childish Masamunes. So my mind got to spinning on why that is.
I love Samurai Kings Masamune because he was just so flawlessly admirable. Even when he got his ass beaten, his spirit and dignity remained centered, particularly on prioritizing True Strengths, like Compassion, especially in his ideals about leadership, which is where it counted most. So when I tried to play the videogames or watch Judge End, I simultaneously fell out of love with Masamune and finally understood some of the silly dork portrayals of Masamune, from doujinshi cirlces (like Propeller Shiki), probably drawn with less basis on the 2009 Samurai Kings anime. -.- Gawd...such a dork... While Samurai Kings Masamune took losses, asking if anyone in his army were killed after he was knocked out, Judge End Masamune was throwing off his loyal soldiers and charging them into an unthinking death gamble, just to satisfy his raging temper tantrum. ~_~; When Katakura called him "Bontenmaru" and hit him before he got his own soldiers killed, I could only nod and agree that he should scold that child. At least Samurai Kings Masamune knew better than to displace his anger onto his loyal, worried soldiers, and would rather just berate his own failings in the rain, through endless sword swings. Maybe it's because the writing in Samurai Kings was heavily focused on reinforcing its themes through characterizations, I've always interpreted Samurai Kings Masamune as primarily motivated by Compassion, while the other versions of Masamune seemed more rooted in their "cool and wild" image, which fittingly have earned him that "snarky brat" reputation in the fandom.
What is integral to any Masamune's character is being "cool", but with subtle differences in characterizing his core motivations, different Masamunes seem to express different types of "cool" from their foundation, up. Commonly, male anime characters are considered "cool" if they are minimalist in their emotional expression. But why they choose to be stoic and what they choose to be expressive about can vary differently, depending on if he's stoic because nothing phases him since he’s secure in him self and never disturbed, or because he’s unphasable since he’s indifferent to everything, or because he's just really repressed, or because he's afraid to express himself, or because he's trying too hard to be "cool", etc. This especially comes up in shipping fanfics, because romance stories usually have to address vulnerabilities in the characters (for couples to bond over). Everyone agrees that the trauma of Masamune losing his right eye, effected the foundations of his character. But everyone interprets this in different ways, which become more pronounced when writing Masamune in shipping fics.
The most logical thing, would be to hear that Masamune's mother Yoshihime pretty much abandoned him, after he lost his right eye, continually tried to undermine his claim to leadership, and tried to poison him, and then think that he has abandonment issues and anxiety about exposing himself to intimate connections again. In this way, Masamune's "coolness" is more a protective facade. Maybe in some ways, this can be more indicative of self-centeredness and seeking external validations (to counteract his mother’s dismissals), more than an already secure confidence. This may also be what sometimes leads to arrogant and childish portrayals of Masamune. His traumatic experience with his mother would cause him to be protective of his inner self, and to always carry a fear of nonacceptance by others. No matter how small he squashed that fear into, he would still carry fears extending from that trauma of his mother turning on him.
But I think Samurai Kings characterized Masamune differently. Instead of the trauma causing him to protect himself, Samurai Kings Masamune seems to have directed his protection outward. His mother abandoned him, so he wants to make sure no one else is ever made to feel that way again. Like Batman, or something. ^o^ He'll even give up things he personally loves (like duels with his newly found rival), if it will protect his "common" soldiers. He'll even build his battle strategies around protecting his armies, by going alone to spring traps himself. It's why entire episodes of that series are devoted to Masamune refusing to abandon even his "common" soldiers. (Though in that specific episode, Katakura knocked him out so he wouldn't preform the rescue; but Katakura did say rescuing the "common" soldiers was Masamune's will.) It's why the farm fields in Date territory are unharmed and actually still existing, even though most of history has proven that it's virtually impossible to keep war away from destroying your lands, especially farmland (unless it takes place on another continent). But Masamune did it on a small island archipelago country, in the middle of constant civil wars, with enemies from all sides. It's clear that protecting even the "common" people are a priority to him. It's why he opposed Toyotomi saying, "Under your rule, only soldiers would be able to live." Like Yukimura, Masamune recognizes that everyday people and a happy quality of life are worth protecting. War for the sake of war was not his goal. Like Keiji said, Masamune knows the difference between a Fight and a War. His goal was to protect people's ability to truly Live. Masamune knows that conquering the country isn't about leadership stroking one's ego, or dragging other people into resolving his personal issues via winning wars, or validating his over-confidence, or gaining all the wealth, or even using the power to conquer other lands. All that stuff Keiji keeps saying throughout the series about life being about finding happiness and living every day with simple pleasures and friendship? It wasn't just to contrast Toyotomi's obsession with obtaining "strength" (as misguided as his definition of "strength" was). It was the same truth expressed by the 3 primary heroes: Masamune, Yukimura, and Keiji. (All 3 of them were most prominent in the 2nd opening theme's sequence.) Protecting ordinary people's peaceful happiness was something Yukimura instinctually felt (but took a long time to understand how to express as a soldier). It was something Keiji lived and demonstrated through his simple vagabond lifestyle. It was something Masamune understood and prioritized protecting, by seeking leadership. And all 3 of those expressions of prioritizing peace and happiness, point to core motivations rooted in Compassion. Masamune was confident enough about his understanding of Compassion's significance, that he was using his Strength to take leadership of the country in order to ensure and extend that Compassion to the people under his leadership. It's why all his "common" soldiers loved him, why everyone was so loyal and considered Masamune so "charismatic". They could all sense that his every action was rooted in Compassion. Aside from his personal desires for excitement (through Fighting), Masamune's every action in Samurai Kings proved that he was motivated primarily by protective Compassion...as his response to his trauma.
Despite it being more likely and reasonable to learn the repercussions of Masamune's lost eye and characterize that as a trauma that is still his weak spot, the Masamune in Samurai Kings seemed to give every indication that he had gotten over it. Which is aligned with his function in that series to represent "always moving forward" and "pressing onward". Having demonstrated the definition of Strength "doing what is most difficult", Compassion, Masamune also demonstrates the morally inapplicable Strength of being unmoved by others' influences. Unlike Toyotomi who tried to convince himself to abandon all his previously held values, by killing Nene, in order to adopt Matsunaga's concepts of "strength" (which were really just Power in disguise), simply because Toyotomi was intimidated and afraid of being put in that mortal danger/fear again (and that mortal fear was somehow enough to convince Toyotomi that Matsunaga’s ideals were correct). Masamune on the other hand is often unmoved from his emotions and beliefs, regardless of the intimidation or Power involved. (Maybe that difficulty in being moved is why he's so intrigued by Yukimura's capacity to "set him ablaze".) Masamune barely flinched when Oda was about to gouge out his last remaining eye, and was even ready to continue fighting if that gouge happened. He wasn't phased when Katakura repeatedly attacked his right side during their duel, even though the person he trusted the most and who should know the most how traumatic the fallout of his lost eye was, was now the one attacking that very spot. In fact, the only time Masamune made a direct motion towards his lost eye, was when he woke up, after realizing he almost got his army killed. In effect, his weakest spot, was concern for his army. Not only that, but all his actions, without directly referring to his right eye, reinforced his characterization as someone unphasable, so secure in himself (which is why he was able to always be so nonchalant; confident vs arrogant), always moving forward, and wasn't bogged down by internal emotional conflict. His vulnerable aspects were no longer fears for himself but fears for the people he wanted to protect. Whatever emotional conflicts he could have had, were probably honed out of his Samurai Kings version in order to better contrast against Sanada Yukimura's characteristic floundering, striving, and Growing in the Samurai Kings series. Compared to Yukimura, Masamune was so focused on the future and already so decided on his priorities, that he never hesitated when presented with 2 "right"/valid choices, the way Yukimura would hesitate. His ideals being rooted in the future (responsibility over everyone in the country) and external (need to protect others), made his present self seem untouchable, unwavering, and just Strong. A “limitless dragon”, as Takanaga once described him. Masamune’s values, his true self, his heart, were all rooted in places/times beyond himself, so he was able to continue "pressing onward", no matter what damage he himself took. Masamune had already matured and felt wise, which was part of his trustworthiness. The Masamune in Samurai Kings seems to have decided on his priorities, so long ago that he never hesitates, because he already has a standard ideal to measure against anything he encounters. In contrast to Yukimura, Masamune had already completed all his Growth.
Foremost, that series used its characters to demonstrate different aspects of the story's overall themes, so there was no room for characters with conflicting, dual aspects. Masamune needed to perfectly represent the True Strength and leadership through the wisdom of Compassion, which that series advocated. That series was all about condemning warfare, while condoning Fighting Spirit and accepting that sometimes battle was a reluctant and hopefully temporary necessity. Only a perfectly wise, mature, and Compassionate protagonist could embody all those themes. Which explains why Samurai Kings made the slight shift in Sengoku Basara Masamune’s characterization, as well shifting the entire Sengoku Basara story to center around Date Masamune.