Rousseau’s “On the Social Contract” begins with this famous declaration: “Man is born free, and is everywhere in chains.”
The opening clause of this declaration expresses a fundamental principle of modern liberalism: every human being is, by nature, free. Yet, Rousseau observes, notwithstanding this native freedom every human being has become enslaved, and the cause of this enslavement is civilization.
Rousseau then set about to explain how this paradoxical state of affairs could legitimately come about. His explanation requires an explanation because in much of his writing he implies that a satisfactory explanation isn’t likely, if indeed it is possible at all, for a profound moral pessimism and moral skepticism pervades all of his writings.
Before proceeding, there is need to clarify some terms.
First, Rousseau was not using the term “slavery” and its synonyms literally, but figuratively. He worried that civilization and its institutions: industry, commerce, wealth, education, leisure, the natural and social sciences, medicine, the cultivation of manners, leisure, and civil government curtail the freedom that is every individual’s birthright. He was not considering these things abstractly, but as they are practiced.
He was a keen observer of modern European states and of the social and psychological effects of their institutions and practices on the individual. For him, our native freedom is not just a right that we sometimes claim, but the deepest of human feelings.
If he’s correct, and I believe he is, you can discover it in yourself. Ask yourself, what does it feel like to be free? And how is this feeling affected in your everyday affairs, and the roles that you play at home, in school, in the workplace, and when negotiating the social and public media? When do you feel most free? How often do you feel that violated, or threatened? Can these violations or threats be rectified? If so, how? If not, why not?
Rousseau labored over such questions. “Man is born free, and is everywhere in chains” is his answer.
“Moral pessimism” is the conviction that human beings can do no genuine good; that any good deed is never pure, always tainted with hypocrisy or self-interest, or worse. Rousseau did not suppose that this inevitable corruption of the moral life was due to some original sin. He believed that mankind is by nature good, and that if human animals were left to themselves in their rustic simplicity to gather food, cohabit, procreate, nurture their offspring and die, all would be well, as well as it is among all other animals in the wild.
The loss of innocence is the inevitable consequence of becoming civilized. Only the savage is noble; savagery, cruelty, and all other social ills, are the ignoble inventions of civilized men, who ruthlessly practice them while artfully concealing their corrupt motives, even to themselves, so that they are also victims by their own corruption.
“Skepticism” is doubt that knowledge, in this case moral knowledge, is attainable. This seems paradoxical, for Rousseau’s writings are full of information about morality. What bothered him was that this sort of knowledge is unable to make us good.
Rousseau’s declaration was neither a passionate outburst nor an idle comment. His two earliest works are devoted to this theme. In his “Discourse on the Sciences and the Arts” he contends that the arts and sciences are rooted in human corruption and become instruments of corruption. “The sciences and the arts owe their birth to our vices,” he writes. “Astronomy was born from superstition; eloquence from ambition, hatred, flattery, lying; geometry from avarice; physics from vain curiosity; and even moral philosophy, from human pride.”
So much for the liberal arts and science, and for liberal education!
In another work, “Discourse on the Origin and Foundations of Inequality” among men, Rousseau argues that social and economic inequality are the unnatural products of civilization or politicization — these terms would have been synonymous for him.        
He does not deny that there are also natural inequalities, but these are mere differences. For example, differences of age, size, strength of body, mental disposition and various talents. They may be accommodated without violating anyone’s native freedom. His concern is about riches, honors, social privilege, social classes and the power residing in them. These are all unnatural products of civilization, and instruments of inequality.
This deep pessimism is not a liberal idea. Liberals tend to be optimists. They believe that civilization promotes moral and material progress, which in turn promotes freedom and equality.
But neither is this a conservative idea. Conservatives believe in an ancient constitution, in an original justice that sanctions class differences and inherited privilege, and their desire is that it be restored. Rousseau did not hold this opinion. He was sure that the only way for us is to go forward. He was an ambivalent liberal, which may be the only honest way to be liberal.
Perhaps the greatest lesson we learn from reading Rousseau’s “Discourse on Inequality” is that civilization is an altogether artificial system of institutions and practices, randomly fashioned by human beings, more often by opportunists than by leaders with noble ambitions. Furthermore, that our senses of civilization’s value are equally artificial sentiments. They are expressions of self-congratulation and flattery, seasoned with denial, cruel delusions that conceal the real effects of civilization: commerce, poverty, war, the capitalization and consequential deformation of the arts and sciences — and, even worse, of popular culture, elitism, the production of useless things and the abuse of human life to achieve it, addiction, manifold diseases, “the whips and scorns of time, the oppressor’s wrong, the proud man’s contumely, the pangs of disprized love, the law’s delay, the insolence of office” and such similar agonies and cruelties.
All this he contrasts with the enviable life of a noble savage, whose existence is a mere hypothesis, for he honestly admits that human nature in its original state is unknowable and unattainable.
If we cannot return to a state of nature, Rousseau concludes, we must make our peace with civilization, using whatever wisdom is available to us to fashion a constitution that causes the least harm and, perhaps, some good. He attempted this in “The Social Contract.”