The Talmud in Kiddushin (22a) explains the word “with you” in every respect of the word. What the master eats and drinks, where he sleeps, in every aspect of his daily endeavor, the Jewish servant must be dealt with and viewed as an equal, and in certain situations as a superior. These laws serve as the basis for the Talmud’s statement of “one who purchases for himself a servant, is like purchasing for himself a master”. The commentators question the apparent contrast between the relationship of a master and his Jewish servant, to an individual and his fellow Jew who is in dire need. Regarding a servant the law as previously mentioned, has him come first, while we find that Rabbi Akiva opines that if two Jews have only one jug of water belonging to one of them, that the owner’s life takes precedence.
Why should a poor man be different than a servant? They have both fallen on hard times and are in desperate need of support from their fellow Jew. Rabbi Meir Chadash Zt”l explained the psychological difference between the servant and the poor man. There can exist between a poor and a rich man a harmony and equalty despite the poor man being deprived of the physical comfort afforded his wealthy friend. Although the poor man can’t satisfy his physical needs, he can still can be viewed as “with you”. However the servant’s being is changed by his subservient situation. Every way that he turns he sees his bitter status, mirrored in a reflection of himself as a lowly servant. Therefore the Torah demands that special attention be accorded to him. For his emotional stability we must be sensitive to all his needs, for he usually views himself as inferior to his master. We may learn from here the importance of understanding that people have different sensitivities and feelings; we cannot impose a blanket rule on a whole group without taking into consideration the effect this rule will have on each individual.