Now this is a strange choice indeed. TWGOK is an anime centred on a hikikomori that refuses to do anything but clear his dating games. Much of it is filled with gaming tropes and hilarious moments that parody the many things that gamers like. So how is the main character of this light hearted series Machiavellian?

Throughout the series, Keima has one goal, just like most Machiavellian characters. And his is a simple one, survival. After accidentally entering into a death contract with Elsie, Keima is forced to capture the hearts of girls who hold the escaped spirits of Hell. To do that, he must raise hell and high water to win their hearts and fill their hearts with love in order to restore the balance of the world and more importantly, preserve his life. Keima will do anything, regardless of how manipulative and cold it may seem, to capture their hearts.

Every action is calculated to precision. Truly, that is the mark of a Machiavellian.

One of the greatest traits of a Machiavellian is their pragmatism and practicality. This lets them conquer their goal, slowly but surely. Unlike most Machiavellians, Shikamaru’s end goal isn’t entirely selfish, because he wants to protect the many citizens of Konoha. However, it could also be said that he is driven entirely from his emotional self-ambitions due to the dying wish of his teacher, and will do anything to see that goal realised.

One such example is the way in which he avenged the death of Asuma. Unlike many characters of the series, Shikamaru planned out the entire encounter with the Zombie Brothers to pinpoint precision. He manipulated their abilities to turn on themselves and caused S-rank ninjas who would normally trounce someone on his level to panic in fear. And to end his emotional onslaught against them, Shikamaru buried the immortal Hidan in a prison that he can never escape, left to die in the ravages of time itself.

Then again, it’s not a bad thing to be a Machiavellian when you’re a ninja, right?

Shiroe is one of the many players who are stuck in the fantasy world of Elder Tale after the game’s latest update. Thrust into an unruly mob of players, his goal is made clear within seconds; the restoration of society. However, in order to do so, Shiroe has to secure a form of leverage that will garner the attention of the many players that are scrambling around in the dark. And he obtained it in the form of food that tastes like food, unlike the virtual salty crap that they have been forced to consume since their arrival.

Using this simple concept, Shiroe was able to corner the market on foodstuffs, and proceeded to coerce the entirety of the player population into forming a round table alliance that places his tiny guild near the top, merely due to his manipulation of the situation itself. Even his in-game class speaks a lot about his character. While Shiroe’s enchanter profession seems to be merely support at a mere glance, it allows him to manipulate the battlefield from afar rather than to get up close to danger.

Just like pulling strings from the shadows, don’t cha know?

Shiba’s goal is very straight-forward and simple; he wants his sister to be happy at all costs. Any other variable is irrelevant and must be discarded off if it causes his sister any form of unhappiness. While it seems that Shiba is just a stupid siscon, he acts borderline insane when it comes to protecting her. In front of her peers, Shiba acts kind and open, giving them a veneer of civility in order to relax them around him.

Behind the scenes, Shiba is killing off people with ease using his high-tech guns. When an enemy ship threatens the home country of his sister, he doesn’t hesitate to fire a god damn nuclear level attack on the ship, atomizing any and all of its occupants into dust. Through it all, he doesn’t feel a smidgen of guilt about his actions, and is able to go home to the comfort of his sister with ease.

That is one scary siscon!

Kiritsugu Emiya once had a goal. He wanted to become a hero of justice and save the lives of the innocent around him. But as he grew older, Kiritsugu became more and more distorted. And as he changed, so did his goal. It warped into a shadow of its previous self, turning into something much darker. Now he wants to save as many lives as possible. And while that sounds noble and good, it becomes a much more twisted concept when examined closely.

If the lives of a thousand can be saved with the death of a hundred, Kiritsugu will not hesitate to pull the trigger on a hundred innocents. Should he be on the hunt for a blood thirsty magus that could kill thousands, Kiritsugu would not even flinch as he blows up the dwellings of the magus while killing the innocents caught in the crossfire, simply because that means more people get to live. His life is a weighing scale, and he simply calculates which decision can saves more lives and executes it without mercy, regardless of the cost.

Fate has manipulated a hero of justice into a monster. And if you stare into the abyss, the abyss stares back at you.

Aizen has one of the more grandeur goals of the bunch. He aims to become god of the world. And this is no lofty ambition, because he has a clear plan to reach it and he almost did in the end. From start to finish, Aizen was manipulating the denizens of Soul Society, tricking them into thinking that he was an unassuming and gentle person who abhors violence. Throughout this time, he caused the exile of countless promising Shinigami and even sent a Hollow to kill a pregnant woman.

Aizen remains ever a monster even till the end. No one can forget the Winter War, in which he tricked everyone into attacking him, when in all actuality it was an illusion of him overlaid on the body of Hinamori, one of the sweetest girls to exist in the series. If the Hongyouku didn’t twist his mind to the point of insanity, Aizen might have even defeated Ichigo Kurosaki and ascended to godhood.
Thank god Aizen didn’t become a god.

Johan isn’t even really his name, it’s just one of many that he has assumed over the years. But for the sake of ease, we will refer to him as such. Johan Liebert is one of the biggest monsters to ever exist in the realm of anime. He constantly manipulates people into causing pointless death and destruction all for his goal. And his goal? It’s just that; pointless death and destruction. Johan revels in the damage that he can cause to the people of the world.

As the central antagonist of the series, the plot that gets unfolded soon reveals the entirety of his manipulations, and what a twisted web he weaves. Almost everything seems to be connected in some way, and the extent of his lies and deceit become apparent when Johan is unmasked for the monster that he is.

That’s what happens when you name your series after your antagonist as opposed to your protagonist.

Shogo lives in a world where society is controlled by a hidden system known as the Sibyl System. The Sibyl System is the judge, jury and executioner of any who strays off the path known as society. There is no longer freedom, only regulation. In that regard, his goal almost seems noble in its conception. Shogo simply wants to overthrow the system in order for society to decide for itself on who should live and die.

But the way Shogo goes about it is monstrous. He helps countless commit crimes of an enormous magnitude, like murdering someone and displaying them like art, for no benefit to himself. The way Shogo operates is in fact very similar to another Machiavellian character, so much so that it wouldn’t be a stretch to call him a consultant criminal. And in the end, how does he try to destroy the system? By throwing society into anarchy by destroying the entirety of its food supply.

Shogo could be the one guy who prevents you from getting lunch. What a monstrous man.

L is most likely one of the most light hearted characters of the ones on the list. That is, of course, if you insist on seeing morality as a sliding scale between light and dark. L is a detective for hire that will solve any case that is deemed too difficult by the investigators of the world. And practically the only reason he does so is to feel the thrill of solving a difficult crime.

When the Death Note related deaths started to occur, L immediately jumped on the case. Just to isolated Kira’s location, he sacrificed an inmate on live television. It doesn’t stop there however. L continues on to torture and humiliated Light Yagami and Misa Amane for weeks on end just to get the answers that he needs to solve the Death Note mystery. In fact, L plans so far ahead with his contingency plans that even in death, he beat Light Yagami through the proxy of Near.

And that’s why he’s on the list instead of Light.

Lelouch remains the mysterious figurehead of the Black Knights throughout the series. He uses his organization to rebel against the tyranny of the Britannian Monarchy. To that end, Lelouch has caused countless deaths, killed the father of a girl who loved him, incited wars and even held the world at nuke point. In the end, Lelouch achieved his goal and became the Emperor of the Britannian Empire. Now as he sits atop a mountain of corpses, he has done all that he has set out to do.

Or as he?

While everything Lelouch has done to become the Demon Emperor would have placed him on this list alone, it is his secret motivation and end result that thrusted him to the top. Lelouch made the whole world hate him. With their hatred centred on a common enemy, he had Suzaku kill him publicly, uniting the world in their hatred of him. This unity would eventually lead to world peace, creating the gentle and peaceful world that he always desired for Nunally.

In the end, it is his single minded pursuit of his ideal that places him at the top of the list. Because not only did Lelouch succeed, he was the one who changed the world the most out of everyone above.