There is an interesting discussion in the Talmud whether a slave of a Jewish owner would prefer to be set free or would he rather remain a slave and have the benefits and security that his master must offer him. (Git. 12b)
A passage in this week’s Portion seems to answer the question. The Torah says if a master strikes his slave so forcefully that he knocked out his eye or tooth he must set him free, LACHOFSHI YESHALCHENU TACHAT EINO, “…he shall set him free in return for his eye.” (Ex. 21,26)
If it is advantageous for the slave to remain with his master for the benefits he has, then isn’t enough that he lost his eye or his tooth that he is further hurt by freeing him from his master and loosing all those benefits?
The obvious answer is that it depends on what kind of a master he has. If his master follows the requirements and the restrictions the law imposes on him, he certainly prefers to stay on. If, on the other had, he has a master that is so violent that he beats him so as to cause major physical damage, and then he is certainly better off being freed and getting away from such horrible treatment.
Everything in life depends on the circumstances. There are no general rules that apply to every situation. We must also not judge another’s actions unless we know all the conditions that brought him to this behavior.