This commandment is a deeply troubling one, and commentaries have been wrestling with it from time immemorial. It is the commandments of the Rebellious Son. This child refuses to listen to his father and mother, and despite their disciplining him, he persists in his ways. He is to be brought to the court, and, possibly, given capital punishment.
The rabbis have worked hard to make this seemingly excessively harsh commandment makes some sense. First of all, they teach us that the Torah has limited application of this commandment so much that, perhaps, never such a case arose. By interpreting every word, we receive requirements such as: the child must be exactly at the bridge age of maturity, a period that lasts about three months, and he must have stolen a certain amount of meat and consumed a certain amount of wine, and that his parents must have similar voices, and that they must be able to walk.
Yet, even by limiting it, it still seems a difficult commandment to understand. Where is the guilt? Why is this child / man being put to death? The sages claim that it is a preemptive punishment. Based on these behaviors, it is a certainty that this young man will grow up to be a criminal of violent nature. It is better for him to die now, while he still is innocent. In this, the sages see a strong proof of the concept of reward and punishment in the world to come.
Nonetheless, this answer raises the question of free will versus God's foreknowledge. How can we be sure that the child will grow up to be a violent criminal, if there is free choice? Perhaps he will repent! One commentary suggests that the phrase, "He doesn't listen to his father's voice and his mother's voice," does not just referred to his biological father and mother. His Father, refers to Our Heavenly Father, and his mother refers to the assembly of Israel. In other words, this child has already rebelled against God and against the people of Israel.
But still, perhaps he will repent? Should we kill him and remove that possibility?
There is a verse in the Psalms that reads,."..[God] Understands to all of their actions." It does not say, "God understands all their actions," rather, "TO all their actions." In other words, God's knowledge of each person is so complete that he can know with certainty how they will behave in every future situation. It seems that the same is true of the rebellious son. The Torah is telling us that, if these symptoms are in place, there is no chance that he will not become a violent criminal.
The commentary Ohr Hachaim points to one word which may be the key to this entire, unusual, mitzvah. The rebellious son, "does not listen." In truth, however, the word for this is mistranslated. Literally, it means, "he is not someone who hears." It's to be compared to the King's guards, who are robbing the citizens. When the citizens come to complain to the King, will these guards allow them in? Of course not. This is what happens when one allows one's evil inclination to be one's ruler, such as is the case with the rebellious son.
I believe that this is the hidden message in the requirement that the rebellious son have eaten a certain quantity of meat and consumed a certain quantity of wine. The eating of meat itself is no great sin! When it is stolen, it becomes a sin. But when the young man drinks wine, he is drowning the spark of conscience with it. This is how he ensures that he will never hear "the voice of his father and the voice of his mother," whether it refers to his biological parents or to God and the Jewish people.
To be sure that indeed it is the young man himself that was the problem, the Torah requires the parents to be speaking with a unified voice. It requires them to attempt to discipline this child. And it requires them to be physically capable of carrying out such discipline. Clearly, their parenting was not perfect, since they are victims of the young man's punishment as well. But it is the young man who has chosen, despite being given an opportunity to grow up in a proper educational environment, to stop listening. If the parents were negligent or incapable of disciplining the child, he would not be deemed a rebellious son. That rebellion must come from within, must include a conscious decision to listen to no one but his own desires.
As we prepare for Rosh Hashanah, the message of this commandment is clear: Listen! Seek out lectures on ethical improvements, on Torah values. Listen to the needs and insights of those close to you. And, most of all, listen to the sound of the shofar, for the shofar is the voice of conscience.