If your brother becomes impoverished and his means falter with you, you shall strengthen him – proselyte or resident – so that he can live with you.
You shall strengthen him: Do not leave him by himself so that he comes down in the world until he finally falls altogether when it will be difficult to give him a lift, but uphold him from the very moment of the failure of his means. To what may this be compared? To an excessive load on the back of an ass. So long as it is still on the ass's back, one person is enough to take hold of it and to keep the ass up, as soon as it has fallen to the ground not even five persons are able to set it on its legs.
Midrash Rabbah 34:1
Thus it is written, Praiseworthy is he who contemplates the needy; on the day of evil Hashem will deliver him (Psalms 41:2). Having cited this verse, the Midrash cites various explanations: Abba bar Yirmiyah said in the name of R. Meir: This verse is referring to one who causes his good inclination to rule over his evil inclination.
Why is caring for the poor proactively a matter of having your Yetzer Tov rule over your Yetzer Hara? What might it mean about a person's character traits? How might a proactive response to other people's troubles be protective for your own future problems? By the way, the Midrash goes on to mention helping people seeking political asylum and helping the sick. Does this change your thoughts on the meaning of the Midrash?
Yerushalmi Ketubot 11:3 (Jerusalem Talmud)
The wife R. Yosi Haglili aggravated him. One day R. Elazar ben Azaryah came by and told him, "Divorce her for lack of respect; it is not befitting that you live with her." He replied, "Her dowry is large." He replied, "I will give it to you," whereupon he gave it to her and divorced her. She married the town watchman. The watchman became poor and blind and she was forced to make the rounds and beg. One day they did not collect anything. He asked her, "Is there not another neighborhood here?" She replied, "There is another street here where my first husband lives, but I am embarrassed to go there." He began hitting her. Just them R. Yosi Haglili passed by and heard her humiliation. He put them up in one of his houses and supported them for the rest of their lives. This he did in keeping with the verse, "Do not ignore your kin," which applies even to one's divorcee. Still one could hear her voice at night saying, "Better the beating from my husband which is but an external pain than the humiliation of being supported by R. Yosi Haglili which is an internal one.
What is this teaching about the loss of dignity?
If you walk in my laws and faithfully observe My commandments
If you walk in my laws: One might think that this denotes the fulfillment of the commandments; but when the Torah states, "and you shall keep My commandments and do them," it is plain that in this passage there is mentioned the "fulfillment of the commandments." How then must I explain "If you walk in my laws"? As an admonition that you should study the Torah laboriously.
A poor person, and a wealthy person, and a wicked person come to face judgment before the Heavenly court for their conduct in this world. To the poor person, the members of the court say: Why did you not engage in Torah? If he rationalizes his conduct and says: I was poor and preoccupied with earning enough to pay for my sustenance and that is why I did not engage in Torah study, they say to him: Were you any poorer than Hillel, who was wretchedly poor and nevertheless attempted to study Torah? ... And if a wealthy man comes before the heavenly court, the members of the court say to him: Why did you not engage in Torah? If he says: I was wealthy and preoccupied with managing my possessions, they say to him: Were you any wealthier than Rabbi Elazar, who was exceedingly wealthy and nevertheless studied Torah? They said about Rabbi Elazar ben Harsum that his father left him an inheritance of one thousand villages on land, and corresponding to them, one thousand ships at sea. And each and every day he takes a leather jug of flour on his shoulder and walks from city to city and from state to state to study Torah from the Torah scholars in each of those places. ... And if a wicked man comes to judgment, the members of the court say to him: Why did you not engage in Torah? If he said: I was handsome and preoccupied with my evil inclination, as I had many temptations, they say to him: Were you any more handsome than Joseph, who did not neglect Torah despite his beauty? ... Consequently, Hillel obligates the poor to study Torah, Rabbi Elazar ben Harsum obligates the wealthy, and Joseph obligates the wicked. For each category of people, there is a role model who overcame his preoccupations and temptations to study Torah.
The Talmud is teaching that we should carefully examine our rationalizations and seek role models who overcame similar difficulties. Are there areas of learning, Jewish observance or ethical behavior that you would like to improve? What are your rationalizations for not doing so? Can you think of counter-arguments?