For a long time, Jun Kiwatari managed to be lucky. As he wasn’t part of any important family, his moderate fortune was enough to keep him in the black ,as far as betting went, and as far away from the School Council’s attention as possible. In that regard, he was free to appreciate the perks of being a winner in his classroom, mostly abusing the female pets that had the bad luck to catch his eye. Among those, the one suffering most was Tsubomi, a girl who had an unfortunate debt of 20 million yen.

Jun is also a risk taker, as he decides to fake a debt to the Student Council in order to participate in the debt relocation game. His plan was to win, so that his debt would be “erased” by getting a 10 million yen check. Since he didn’t have a debt to begin with, he saw it as winning an easy 10 million. After all, none of the students who had real debts could be as good at betting as him.

And while said plan didn’t work, mostly because he ended up facing Yumeko and Meari, his long time survival in the school earns him the tenth place on our list.

Itsuki is one of the most approachable and apparently nice members of the Student Council at the time the story starts. She’s the daughter of the owner of a toy company, and thus, she gets to have her own personalized cards and games in order to keep on betting against other students. Still, she doesn’t get much respect from the other members of the Student Council because she got her position not by gambling, but by giving a huge donation from her personal fortune.

Itsuki, at first, only helps to support the theory that she has no skills at gambling. Her duel against Yumeko shows that she has one specific trick: since she can get personalized cards made, she can also mark them in thermal ink that disappears quickly. Thus, she knows what cards her opponent has if she plays poker, or if she plays memory, she knows exactly where each pair is. But once she is defeated once, she starts climbing back to the top off-camera by joining Yumeko, and showing she has an amazing poker face.

Since we haven’t seen her bet again, she can’t climb higher than the ninth place on our list, but that doesn’t mean she doesn’t have a great talent for bluffing.

At the beginning of the series, one is pressed to say that Ryouta is one of the characters with the least talent for gambling. In fact, he dislikes gambling, and we meet him when he is losing his right to be a person against Meari Saotome. We’ll talk about her later. And yes, he considers himself a bad gambler, but when he meets Yumeko, he starts learning from watching her. Most of the time, he is wishing she’d quit when she’s ahead or thinking she may have a plan that he still can’t comprehend in order to come up on top, but he still watches with more attention than her opponents.

And that is what makes him a lot better than his classmates. He pays attention, and starts making connections, which means that if he actually gambled on his own, he’d be quick to figure out if his opponent cheated. But once he met Yumeko, he quit gambling and started just watching. This makes it hard to figure out how much better he has gotten at the actual table, but we get the chance to see that his poker face has improved a lot.

Because of the possibility of him becoming a lot better the more he watches Yumeko, he earns the eighth place on our list.

As part of the Student Council, she heads the Beautification Club, which means she is in charge of making sure that no one steps out of line regarding the ethics and moral rules at school. But the thing is, she’s not very interested in that, and rarely ever intervenes if there’s not a risk to her own life. There’s not much gossip about how she gambles, mostly because her gambles are insane: where others go for money, or at most some physical damage, she goes straight to Life or Death bets. She in particular enjoys making different variations of Russian roulette, not because she wants her opponent dead, but because she wants to die.

Midari is not completely insane, despite the evidence. Every one of her gambles is rigged so she will lose, so that the person gambling against her won’t be badly hurt –except for the fact that they’ll be a murderer, but Midari doesn’t consider psychological trauma. This is because before she got involved with the Student Council, she won so easily at everything that she completely lost interest in life, until she took her own eye to repay a gambling debt. She’s searching to feel that thrill again and is convinced she can only feel it if her life is on the line. Unfortunately, this makes her cheat often and earned her the scorn of the only other person in the anime who understands the desire to bet everything on a longshot.

Since her craziness often gets in the way of her gambling, Midari only reaches the seventh place on our list.

Yuriko is the head of the Culture Club, and yet another member of the Student Council, which means she’s considered one of the best gamblers in the school. In her club, the games are made in a way that there is a house advantage, but it’s so small that most people never realize that Yuriko cheats. This may look unfair, especially when she forces pets into higher and higher debts, but we must remember that the school’s philosophy on gambling includes the ability to bluff and cheat without being discovered, not on the fairness of the game.

And despite the fact that she looks meek and easily bullied by the rest of the Student Council, the truth is that Yuriko is the only Council member that seems to be against the Pet system, since she has made arrangements that every member of the Culture Club is not allowed to be part of the system so none of her girls can become Pets and thus, keep some sort of freedom for themselves. To keep her girls free, however, Yuriko has to keep her place in the Council and thus, she is ruthless when it comes to gambling.

This is why Yuriko, the mild-mannered girl who always wears a traditional kimono, earns the sixth place on our list.

Of all the Student Council, the only one who has absolutely no interest in the inner politic fights is Yumemi. While she appreciates the perks that come with being part of the Council, she is aiming way higher than just controlling the school. What she really wants is to become a Hollywood star and is willing to do anything that is required of her. In order to reach her dream, she plans to use the contacts she can create at Hyakkaou, as well as her growing fan base, to catapult herself to a role in the USA, as she thinks Japanese actors have little chance to succeed in the international market.

While she doesn’t gamble as often as other members of the council, that doesn’t mean she’s not ruthless when she does it. She doesn’t cheat directly, like others, but instead what she does is to make sure that all the odds are in her favor while pretending that she is the underdog. Even Yumeko is impressed by how she decided to gamble everything not on a game, but on her dream and thus she even uses her loses to keep ahead. While we never see her gamble in a traditional game, because she prefers events where her fan base gives her a slight advantage, we have to admire her ruthlessness when it comes to beating her opponents.

And this is why she earns the fifth place on our list.

Speaking of ruthlessness, that is the main characteristic of the Treasurer of the Student Council, Kaede Manyuda. He’s in charge of all the Student Council’s money, and in many ways, the one in charge of the ways in which they can cash in on the other students’ debts. He prides himself in being able to decide if a person has worth as more than a puppet from a glance, and has been raised to believe that if you can’t be the best on the road you’ve been put on, you’re worthless. Yes, this means that his own parents told him that if he didn’t reach the top of the career they had chosen for him, he was a failure.

When he gambles, he only plays a safe hand. He’s good at mathematics, which means he can consider all the possible outcomes easily, and thus, he can always bet on a winning hand. The fact that he is excellent at reading people, even when they try to keep a straight poker face, also helps with his particular brand of bluffing. Once he knows your strategy, he will go for the kill. If he can also humiliate the other party as he wins, it will make him feel even better when he destroys his opponent.

All these reasons, plus the fact he has money to spare in order to keep raising the stakes, earn him the fourth place on our list.

Meari Saotome is the first serious gambler we met in Kakegurui, just as she is dooming Ryouta to a life as a pet in the school. She has an excellent poker face and can lure you into believing you have the upper hand just with a smile. She was the top winner in her classroom before Yumeko arrived, and had a reputation thanks to her winning streaks that reached even the ears of the Student Council. Sure, she cheats; everyone does at Hyakkaou if they want to keep winning. But where others keep cheating with one strategy thinking that no one will ever catch on, Meari learns from her mistakes with Yumeko and starts changing her way of betting. Not only that, but also, her particular brand of cheating originally left enough to chance that she also could feel the thrill of the gamble.

Meari is one of the few people that realizes that Yumeko’s brand of gambling is going to change everything in Hyakkaou, especially after she loses badly against the newcomer and has to live as a pet for a short time. This allows her to realize how much the Student Council looks down on the rest of the student body and if there’s something that she doesn’t tolerate, it’s when people look down on her. With newfound resolve, she decides that she will bring down the council before letting them control her life again.

Due to her resolve, and how much she is willing to learn just by watching Yumeko, Meari earns the third place on our list.

Yumeko is the main character of the series, and she breathes and lives gambling. Nothing, absolutely nothing makes her happier than the thrill of risking everything in a high-risk bet. Even if she’s not the one doing the gamble, she loves watching people going down the same path towards madness that she walks in. Now, normally, such an addict to gambling would be completely broke and in need of a family intervention: after all, she has no limits when it comes to a bet and if she’s allowed to, she will bet billions of yen even if she doesn’t have them at hand; however, she is also an excellent gambler, and if someone cheats on her, she will find the way to turn it against the cheater.

Now, this doesn’t mean that she always wins. On the contrary, in the anime, we see her take some huge losses, and at one point she even loses enough to become a pet and have her life controlled by the Student Council. But this is what makes her so good at gambling: As long as she’s alive, she will find a way to make crazier bets and come back on top. Or at least, keep doing what she loves: gambling and making others gamble their lives with her.

Because of her ability to rope others into her madness, and the fact that we can’t be sure that losing is part of her overall strategy, Yumeko occupies the second place on our list.

The President of the Student Council and the absolute ruler of Hyakkaou Academy, to the point that she doesn’t consider it a school, but her own personal aquarium where she can see human nature at its best. It was she who made Hyakkaou into the gambling house it is when Yumeko arrives, by beating the previous President and making gambling compulsory, instead of an extracurricular activity. We rarely see her play, but when she plays, the stakes are so high that even those who watch the games feel like they are the ones whose lives are on the line.

Unlike Yumeko, who seems to be content with the actual act of gambling, Kirari plays to win. She has many ways to hide her plans, even from her own allies, like her assistant Sayaka Igarashi, or her right hand, the Vice President. She seems to have no morals and only wants to be amused. This leads her to directly influence others’ gambles, either by allowing increasingly high bets or by outright cheating. This is what makes her Yumeko’s goal: the other girl won’t rest until she has the chance to bet against Kirari. And Kirari is willing to bet that Yumeko will risk everything to make it possible.

Because she never loses, and manages to rope everyone into her web, Kirari more than wins the first place on our list.