If it were possible to ascertain the actual political philosophy of Zhuangzi, I am not at all sure that I would like it. There are other things he has to say which I don't like, but which I recognize as remedial — I don't like them because they cut against the grain of my "typical human inclinations". Zhuangzi's intention is not to tell us what we want to hear, but what, should we allow it to open us to other possibilities, though initially painful, might ultimately lead us to greater happiness. Thus, I must ask myself if I dislike Zhuangzi's political theory because it does not seem to me to be the 'moral' approach — we do have social responsibilities after all. And that immediately sends up a cautionary flag, for as soon as we start speaking of "the right thing to do" we have moved from freedom into bondage. It is not that the right thing wouldn't in any case be done, but that it would be done still more rightly, that is, more effectively.
The best place to start in coming to grips with Zhuangzi's political theory is to try and understand what it is, but this can only be an approximation — there is sufficient ambiguity and apparent contradiction to make this a tentative exercise.
At the core, he has definite Yangist tendencies. A. C. Graham has speculated that Zhuangzi might very well have at one time even been a Yangist. According to Mencius, Yang Chou would not have sacrificed one hair from his shin to save the world. This is no doubt hyperbole, but provides us significant insight into what he was about. His core belief, it seems, was that one's greatest responsibility is to survive. Zhuangzi seems to agree with this principle.
Yang has been labeled a 'hedonist', though much of the weight for this appellation comes from a spurious work in the Liezi attributed to him. Though even present day scholars continue to label him thus, I think it both unfair and misleading.
It is easy enough to see why Zhuangzi would feel sympathy for this principle. This, above all else, is what life does. Life is an impetus to live. And Zhuangzi's core belief is that we do best when we let life express itself through us. We are enjoined to “not add anything to the process of life.” Sacrificing oneself for some ideal is doing just that. Is this making us uncomfortable, yet? Going against our potty-training, is it? Not what we were taught in Sunday school?
Following this principle one would not “die for his country” or to “keep the world safe for democracy”. We might be able to get our moralizing minds around this, but what of sacrificing ourselves to save our child? There are always hypothetical counter-arguments, because life does not follow principles and rules. But here I think Mencius had it right when he suggests that anyone (normal) would jump to save a child from falling into a well without weighing the pros and cons of such an action. It is spontaneous, and that is the whole point.
You can check out Scott's writings on Zhuangzi here.