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This included the demon town. After all, the only way to truly escape the Arena was to escape the town. That was the true security and enemy of anyone willing to escape.

However, he was not so foolish as to believe that they could outrun a horde of demons.

Besides, these demons were always hungry. There was a reason why no gladiator who had ever escaped the Arena had made it out alive.

Even old Buckle, who had been able to escape many years ago, spoke of the horrors that his comrades faced going into the town area.

Once a human was out there, he would become food that would no sooner be toyed with than eaten alive.

It was for this reason that many gladiators relegated themselves to surviving within the Chimera Ant Caves underneath the Arena.

Even Crusher said that it was an easier world down in the caves than it was outside.

Lenny had thought hard about this, but at the time, he did not have a solution that was feasible.

Of course, he could always break through and grow in strength until he reached a defining point where he could run away.

However, Lenny was not a fool.

As the old saying goes, A Shark cannot get bigger than its tank, or a snake its hole. 

He knew for certain that if he remained in the Arena, his growth would be stunted.

It was only by luck that he was able to get the Angel feathers. Such luck only happens once in a blue moon.

Besides, there was the obvious doubt that Cuba would allow him to grow that far and that big before turning him into a Magistri.

The best option was to figure out an immediate way out.

The moment Lenny had seen A123 use his ability in the Devil Dungeon

Right there at that moment, he knew that this was the one he was looking for.

This was the person who could do it.

After all, why fight the demons if they can fight and destroy themselves?

It was for this reason that he was willing to give in to the threat of Cuban when the Arena master played Russian Roulette with the lives of his teammates.

One must make sacrifices for the overall good'. 

Lenny was more than willing to take all the beating and torture for three days straight, convincing Cuban that he could not be broken by anything other than the safety of his comrades.

Why?

The answer was simple. Cuban never allowed any gladiator who had graduated from the Arena to escape.

All of them were turned into Magistris, and those were just A-class gladiators.

How much more his own teammates, who had survived a Devil Dungeon and now showed incredible Rank 1 lesser demon strength,I think you should take a look at

In fact, if Lady Vinegar had not spoken about Lenny, reminding the demon of Lenny's broad usefulness, then Cuban might have turned Lenny into a Magistri the moment they got back home.

Lenny had discovered from the Magistri's mouth that the moment a Gladiator's heart was eaten and Cuban's blood was in his veins, that Gladiator would lose his special abilities, inheriting Cuban's blood abilities as a replacement.

This meant that if A123 were to be turned into a Magistri, he would lose his ability.

That same Ability that Lenny considered integral to his plan

The only reason Cuban had not yet touched C888 and A123 was that he was using them as bargaining Chips for Lenny to do as he pleased. After all, a full three days of torture had done nothing. This was 'supposedly' the only way to break Lenny.

Of course, this was just as Lenny had planned it to be.

Next, Lenny used the small window of opportunity when Cuban left him with his friends in the room to convince A222 to agree to his escape plan.

Lenny had studied his teammates well.

Their connections, their bonds, their beliefs, and even their subtle fears

In the short time that they had spent together, he could predict the kind of actions they would take depending on the kind of information that they were fed.

Such was the way of an Assassin.

Information was an important lifeblood in his trade.

There was a guiding Saying to Assassins concerning this in his former world: If one should put Information and Knowledge first at all times, the money will never stop coming and the blood will never stop flowing.

Lenny used the knowledge he had about them to his advantage.

Because of the kind of gift A222 was given at birth, she saw the world in a different light.

A gladiator's world was cruel, but it was nothing compared to what she had to go through for most of her life.

One would think that her heightened senses would make her bold and fearless.

However, it had a different effect on her.

Her senses always fed her the harsher truth of the world. This made her quite fearful of it.

She became so fearful that she was willing to betray the order of Gladiators, acting as a right-hand man to the Order master, who was really the Magistri in disguise, just to save and preserve her own life.

This was a very selfish act.

But Lenny did not truly blame her. Human beings are such creatures at the core of their nature.

Self-preservation was an instinctive action.

An example would be a newly born child that would cry whenever it was hungry, sad, or even uncomfortable. The child did not care whatsoever about how its mother was feeling, only that it was satisfied.

All human beings have this need to want to put themselves first.

Of course, the only known solution to it was a concept human beings, as an intelligent society, invented for ourselves.

It was known as...LOVE.