Kotomine Kirei
Now without trying to spoil too much beyond the 1st Ep, let me just say that Kirei has always been a lost youth. A lost sheep so as to speak. But if there's anything to go by, he's indeed a wolf in sheep's clothing and the scariest fact is that he doesn't really realized it until later in-plot. Now this is a man wholly evil as proven by Fate/stay night, but what truly caused the devil for what he is? You can just ask any Christian on what made Lucifer Satan and he/she will tell you it's down to pride and arrogance. For Kirei, we're talking about a Satan incarnate without the ego factor.
In fact, there's a very good reason why Kiritsugu FEARS him. Because out of the other Masters, Kirei was that sole unknown factor. The wild card, the joker of the deck... or perhaps even more fittingly, the sole Devil within a stack of tarot cards.
Now what was Kiritsugu's verdict on Kirei? Someone whose background was perfectly sounded out just like the rest, only to realize that whatever being understood only served to throw up a far greater question unanswered. Namely why did the Grail choose him as one of the seven? Kiritsugu knew why he was chosen just like how he knew why the rest were chosen (apart from Uryuu Ryuunosuke whom I'll NOT be covering here due to him not yet revealed officially), but not Kirei.
So what's Kirei's ambiguous factor all about? According to Kiritsugu's research/analysis, Kirei is someone who could have been one of the greatest masters in whatever field of expertise he partook in. Yet, he chose to bail out upon nearing that most desired end called "success". Why? Kiritsugu couldn't come up with an answer as well apart from the fact that Kirei couldn't really find fulfillment in whatever he tried and ultimately excelled in. Everything being known about Kirei was merely superficial in nature, but perhaps what truly struck the fear in Kiritsugu himself is this: He sees a certain mirror of himself in Kotomine Kirei.
Ironically however, no one actually understands Kirei right from the start as in no one actually noticed he is a broken young man still trying to find a purpose in his life. Apart from Emiya Kiritsugu that is. And this final part, my friends, should be what truly made the whole logic utterly ironic since both are essentially strangers only knowing each other via third party sources more than anything else.
Interestingly enough, the only reason why Kirei was to join Tokiomi as his protege is down to his father, Kotomine Risei.
As a father, Risei only wants the best for his son, yet he has never understood his son.
As an expert appraiser of his talent, Tokiomi has never cared about whether he should try understanding Kirei firstly and foremost.
Laughably enough, the entire farce is caused by an underground alliance of sorts between the Tohsaka family and the Kotomine family, i.e. between Tokiomi and Risei. In short, the need to honor an alliance for the sake of victory has effectively forced Kirei onto a path of no return.
A solitary path reaching all the way to Emiya Kiritsugu himself...
A mere stranger whom Kirei has subtly deemed to be his mirror image...
And his only hope to self-discovery and perhaps self-purpose as well.
Emiya Kiritsugu
While it's arguably true that every Master is a selfish bastard in his own right (Kariya included of course), there's a very good reason why I adore Emiya Sr the most in the entire series. Episode 1 actually portrayed forth TWO different Emiya Kiritsugus. The first Emiya Kiritsugu is the devil himself. Someone used to being vilified, yet so valuable as a pawn in the eyes of the Mage's Association. The other Kiritsugu? Well, he actually appeared right at the beginning before Tokiomi and Kirei delivered their individual takes on him. Now let's dissect the difference on three different levels. Or rather three different characters' POV.
Firstly, let's talk about Tokiomi
To him, Kiritsugu is indeed nothing more than a pawn for hire. A mercenary hired to kill heretical Magus, i.e. those who escaped from the Association. Now the rule about any Magus is this: no Magus, and I really mean NO Magus should be revealed as such under public scrutiny. This will invite unwanted trouble for the Association mainly because the Association itself has effectively detached itself away from the everyday society. Secrecy is the unspoken golden rule and anyone breaking this rule will surely invite trouble.
In the worst case scenario, such individuals will end up creating unwanted disaster for the society at large. Simply put, he's being hired for a price, his mission is to accomplish the dirty job for them. In exchange of course, the Association can just easily feign ignorance should shit truly happen.
Yet, Kiritsugu's record as the Magus Killer is pretty much a 100% sure kill rate and a 0% failure rate. The biggest reason is down to his unconventional methods of being a one man terrorist. Yes, folks, Emiya Kiritsugu IS a terrorist no matter how you look at it. In short, he's utterly capable of bombing public places full of innocent people if it means accomplishing whatever that is at hand. Yet at the same time, acts of frontline assassination will always be used in conjunction with such heinous means. And why all the unwanted bloodshed? Tokiomi's verdict was that of derision. To him, the name Emiya Kiritsugu is nothing more than a stain or a random social scum. To him, Emiya Kiritsugu is most likely killing only for the money.
A/N: To try understanding why such tactics can truly work against any heretical Magus, maybe we should ask ourselves one very simple question: if you're the one being hunted down, should you opt to hide behind multitudes of innocent people or will you just bust your own cover away just because you happen to believe yourself to be the second Onslaught? (cue the Marvel comics reference in case you still don't understand the parallel)
Then let us come to Kotomine Kirei
Now this is one interesting POV we're seeing here because the Emiya Kiritsugu in his eyes is NOT a mercenary. Unlike his aforementioned mentor, he actually bothered to go a further mile in trying to understand why such an extremist individual has to exist. Is it down to an innate instinct telling him beforehand that this Emiya Kiritsugu may not be that simple? Maybe we should just narrow it down to Kirei understanding Tokiomi's character in order to make the reason easier for us to digest.
Of course by then, both teacher and student would have known that the Magus Killer had gone MIA for 9 years in total prior to receiving the relevant information. Of course since Kiritsugu is pledging his service to the Einzbern family, Tokiomi would have definitely still remained defiant in his stance.
But not Kirei. To him, there HAS to be a reason behind that 9 year hiatus defying the much feared repute rightfully earned. Upon understanding that Kiritsugu was also being a freelancing hitman during periods of war, Kirei's curiosity was finally piqued for good. Because he realized one very special common ground: that Emiya Kiritsugu will always make his presence known when/where the fighting would always be at its fiercest.
But not Kirei. To him, there HAS to be a reason behind that 9 year hiatus defying the much feared repute rightfully earned. Upon understanding that Kiritsugu was also being a freelancing hitman during periods of war, Kirei's curiosity was finally piqued for good. Because he realized one very special common ground: that Emiya Kiritsugu will always make his presence known when/where the fighting would always be at its fiercest.
Now anyone understanding the basics of warfare can AND will tell you that when the fighting is at its very peak, be it any specific front or any specific period, that can only mean one thing:
The difference between victory and defeat will more oft than not depend on such moments.
Kirei isn't a fool because he knew what this truly means. To put things in a nutshell, it's a case of "kill or to be killed". Or rather "win or to be killed". Which is why he actually stated to himself that Kiritsugu seems to be someone "constantly chasing Death". Is it his own death or the death of others? I truly doubt Kirei knows the answer of yet, but if there's anything to go by, it's very likely that Kirei is now starting to believe that like him, Emiya Kiritsugu is an empty shell of a human being trying to find his own purpose as well.
And lastly, we have the most (?) unexpected candidate...
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Upon the first opening scenario, we're greeted with a picture filled with warmth behind the backdrop of a heavy blizzard (which in an imagery sense, can be seen as a case of foreshadowing where the upcoming slaughter is concerned). Within the comfort from one of the rooms in Einzbern Castle, Ilya was born (yes, I'm talking about that loli in Fate/stay night). Upon Iri's plea for Kiritsugu to embrace their daughter (and it's true that Ilya IS their daughter), what was Kiritsugu's answer? He said that "he has no right to embrace the child" and fullstop. So why did Kiritsugu say that?
Was it down to playacting? If so, then what did he have to gain from the whole episode knowing full well that a flat "no" can just do the trick equally well, if not better?
But if it's not down to playing up a facade, then why did Kiritsugu choose to condemn himself in the worst verbal manner possible?
He never faced Ilya even once, why? Because the reason is very simple.
The devil has never been truly black as others painted him out to be. Emiya Kiritsugu is a selfish bastard, make no question about it. But Emiya Kiristugu is also a character on a specific mission. In short, he has something to achieve in life. And he has to be utterly selfish for the sake of that something.
Simply said, everybody has the right and choice to despise Emiya Kiritsugu, but NOT Iri. Why? Because she understands the real Emiya Kiritsugu.
Interestingly enough, Iri said that if not for Kiritsugu, she would still be a puppet. Why? Because her only fate is to be the Grail's physical vessel, yet somehow and for some reason, Kiritsugu gave her another life far more deserving. That even though she can never escape from such a fate, she's able to at least live like a human being until then. To her, it's the best gift she could ever wish for. And Kiritsugu has granted her that gift called a purpose in life.
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