The Torah obligation of respecting parents, which is included among the Ten Commandments, extends so far that it requires one to avoid disrespecting his parents even if they acted against him. Even if one’s father threw his wallet into the ocean, he may not react angrily or embarrass his father. The father in such a case certainly bears liability, and the child is fully entitled to take the father to Bet Din and demand that his financial loss be compensated, but even so, he may not humiliate or speak angrily to his father. Another case mentioned in Halachic sources is where a parent publicly went up to the child, tore his clothing and humiliated him. The obligation of respecting parents requires the child to remain silent and not cause the parent humiliation in return.
However, the obligation of respecting parents does not require one to lose money for the sake of showing his parents respect. Thus, for example, if one sees his father planning to throw his wallet into the ocean, he is fully entitled to try to convince the father not to, and, as mentioned, he is entitled to take the father to Bet Din after the fact.
In light of this Halacha, the Rabbis noted a question that arises from the famous story told in the Gemara of Dama Ben Netina, a non-Jewish jeweler in Ashkelon, who turned down a lucrative deal out of consideration for his father. The Gemara relates that the Jews approached Dama to purchase a certain precious stone that was needed for the Kohen Gadol’s breastplate, and Dama refused to sell it to them, because the key to the safe was under his father’s pillow, and his father was sleeping. In the end, Dama was rewarded for his sacrifice with the birth of a Para Aduma (red heifer), which he sold to the Jews for a large sum. The question arises as to why Dama did not wake up his father in order to avoid the loss of this lucrative deal, given that the command to respect parents does not require losing money.
The Ran (Rabbenu Nissim of Gerona, Spain, 1320-1376) offered two answers to this question. First, he explained that although one does not have to lose money for the sake of showing his parent respect, he is required to sacrifice money to avoid causing his parent distress. Therefore, Dama forfeited a lucrative transaction in order to avoid causing his father distress by waking him. Secondly, the Ran writes, a distinction exists between sacrificing money and sacrificing a profit. Dama did not lose money he already owned, but rather an opportunity to earn more money, and this sacrifice is, in fact, required for the sake of respecting one’s parent.
On this basis, the Rama (Rav Moshe Isserles of Cracow, 1530-1572) writes that one must be prepared to forfeit money-making opportunities for the sake of respecting his parent. Although the Misva of honoring parents does not require losing money for the sake of one’s parents’ honor, it does require losing profitable opportunities for the sake of one’s parents’ honor.
Summary: The Torah obligation to respect one’s parents goes so far as to require silence if one’s parent caused him financial damage or embarrassment, though in such a case the child may take the parent to Bet Din to demand compensation. One is not required to lose money for the sake of respecting his parents, but he is required to forego on profitable opportunities for the sake of respecting his parents.