Of the five branches of philosophy, the fifth is Aesthetics. Its surface question is “What is beauty?” Dig a bit deeper and the questions become ones like “What is quality?” and “Why do we like whatever we like?”
My theory is that we are drawn to things that resonate with us. This has more to do with how we perceive it and how we perceive ourselves in relation to it with little to do with the thing itself. With this is mind, ask yourself dear reader, who is your favourite Assassin and why?
My favourite is Edward Kenway. This is not to say that he is the best or ideal assassin. That position is reserved for the likes of Altair or Ezio (though I'm on team Ezio with this one). For the entirety of the game Black Flag Kenway isn't even an assassin. At the end he says that he has issues to sort out and that he would join the brotherhood when they are done, which he does. I like Kenway because I identify with his story about a Jackdaw trying to be an Eagle. Ezio is noble, wise, and has clarity of purpose. He is the quintessential Eagle. Edward Kenway is not.
In animal lore, the Jackdaw is equated with thievery and both craftiness and foolishness, he's too clever for his own good. He is the kind of person who does things the quick and easy way, is smart enough to succeed to a point, but is scrambling to hold that position and never feels truly worthy of it because he feels he did not earn it. Living in constant fear of being caught out for the fraud he believes himself to be.
As Mary Read tells him, "No one honest has an easy life, Edward. It's aching for one that causes the most pain." Her point here is that people have what they have because they sacrificed freedom and ease to get it. Those unwilling to make the same sacrifices see the "easy life" these others seem to have and want it for themselves. They ache for the benefits but do not want to pay the cost.
Aristotle called pride the crown of virtues. In other words, pride is the reward for living a life of positive habits. The opposite is arrogance where someone expects the benefits of virtue and pride but lack the works to back it. . An arrogant person is the kind who demands respect but has done nothing deserving respect. Rather than fullness, for the arrogant there is only emptiness
Imagine a cup and no matter how much you pour into it the cup never fills. The trick is that to everyone watching the cup is overflowing and you're making a mess. Doc Holiday in the film Tombstone describes his nemesis, Johnny Ringo, this way. "A man like Ringo has got a great big hole, right in the middle of him. He can never kill enough, or steal enough, or inflict enough pain to ever fill it. " Edward Kenway suffers the same affliction. He can never steal enough or become renowned enough to bolster his sense of self-worth. He's never good enough in his eyes despite his acquired wealth and fame. He is contemptuous of people of accomplishment, status, and rank because he believes that he deserves it more than they do.
Of course this is fiction, but in real life it's the same principle -- without the violence. We each have an idea of ourselves that we carry around with us. Commonly called the self-image. The question is whether this image is consistent with reality or not. A person who sees their cup as empty is constantly looking to fill it, but since the problem is one of perception not abundance, enough is never enough. Such people may have lives filled with money, power, respect, love and be the envy of others, but they lack the capacity to accept the fact that they have these things and therefore constantly strive for them.
Kenway was born to a poor family working the farm, but he always knew that he was meant for more. It was almost as though he saw the bigger picture while his family and neighbours saw only pixels. Some people are happy with the world they are given while others see and therefore want more. This is often the case with heroes in stories. They are set apart from the other characters because they see, or at least sense, a world beyond the mundane drudgeries of life.
The first example of Kenway reaching above his allotted station in life is made evident in the novelisation of the game to explain his motivations for leaving Caroline to make his fortunes as a privateer. He had won the heart of most beautiful woman in the area but her family was rich. Of course her parents disapproved of her marrying beneath herself and Edward came to resent the two of them living in a shack on his parent’s farm. Caroline was okay with this because she loved Edward, but he couldn’t live with himself. He needed to prove that he was better to Caroline, to her family, and to his neighbours. He needed to become rich.
Money is useless. It's just bits of metal, paper, or bytes. So the pursuit of money is also useless. But people do not pursue wealth for the money. They pursue what the money represents. For Edward, the pursuit of wealth was the pursuit of love, self-worth, and freedom.
It's been said that the people who say "money isn’t everything" are people who have it. They take money for granted and do not appreciate that having money enables all the great things that "money can’t buy", like love, self-worth, and freedom. However, St. Columba wrote that the man who is not satisfied with little will not be satisfied by more. Money enables what is already there. It's like how Dr. Erskine describes the super soldier serum in the film Captain America. It “amplifies everything that is inside, so good becomes great; bad becomes worse.” This is true for all forms of power.
For Edward Kenway becoming rich drove him to want to become richer, possessed of the "one last big score" mentality. He became so obsessed with acquiring the means to his end that he forgets his end purpose of returning to Caroline. He reaches rock bottom with the death of Mary Read while in prison and the grief driven drunken binge that followed. It is during this haze that he envisions his nemesis, Woodes Rogers, taunting him with Aesop's tale of the jackdaw.
"Aesop once wrote of an eagle, soaring high above a shepherd's field that swooped down on powerful wings to seize a grazing lamb and carry it off to her nest. Flying close by, a jackdaw saw the deed, and it filled his head with the idea that he too was just as strong and capable. So with a great flapping and rustling of feathers, the jackdaw came down swiftly and clutched at the coat of a large ram. But when he tried to fly away, he found he could not lift the animal, for his size and strength were not up to the task. And even as the jackdaw struggled, the ram hardly noticed he was there. Nearby, just across the field, the shepherd saw the fluttering bird and was quite amused. Running up, he captured the jackdaw and clipped its wings. That evening he gave the jackdaw to his children as a gift. "What an odd little bird this is, father!" they laughed and shouted. "What do you call him?" "This is a jackdaw," the father said. "But if you should ask him, he would claim to be an eagle."
This is the central point of the story. Edward Kenway is the jackdaw. He coveted the positions of the rich in his neighbourhood growing-up and believed that money would make him noble. He dresses-up in the robes of an Assassin, but has not earned the right to do so. He pretends to be Assassins throughout the story and granted he has the innate skills to pull it off, but he is no Assassin. When he fails he sees himself as the fraud he is, but in doing so he transforms.
For years I've been rushing around, taking whatever I fancied, not giving a tinker's curse for those I hurt. Yet here I am... with riches and reputation, feeling no wiser than when I left home. Yet when I turn around, and look at the course I've run... there's not a man or woman that I love left standing beside me.
It may seem a trite lesson. "I sought riches but all I needed was love", but it's deeper than that. It is about the cup that never fills, like some tartarusian torture, and a lesson in how to fill it. If you aspire to greatness, to be the hero or the Assassin, or to be loved and respected, it is not enough to pursue to benefits or trappings that you associate with these things. Dressing like a doctor does not make you one. Rather you must pursue to virtues that result in these benefits. If you want wealth, then develop positive work habits and an eye to spot opportunity. If you want love from others, then learn to respect their thoughts, feelings, needs, and space instead of assuming that yours somehow trump theirs.