Midrash, for those unfamiliar, is a way of interpreting the Hebrew Bible, digging deep to uncover hidden meanings and moral lessons. And in Midrash Tehillim, a collection of interpretations on the Book of Psalms, we find some pretty clear guidance on this very issue.

It all starts with a verse from Proverbs (16:19): "Better to be lowly in spirit along with the oppressed than to share plunder with the proud." It's not always easy to choose the side of the underdog, is it? There's often more immediate gratification, more apparent "success," in siding with those who already have power. But the Midrash suggests that true happiness lies elsewhere.

It continues, “Happy is the person who takes care of the oppressed and behaves humbly.” It's a powerful image, isn't it? Someone who actively seeks to lift up those who are down, someone who chooses humility over arrogance.

But what about the alternative? "Woe to the person who takes care of the wicked," the Midrash warns, "as they will take care of their own interests and then depart from the world." Ouch. That stings a little, doesn't it? It's a reminder that aligning ourselves with those who are only out for themselves is a ultimately a dead end. They might use you, but they won't sustain you.

The text continues with a verse from Psalms (37:10): "A little while, and the wicked will be no more; though you look for them, they will not be found." It's a stark reminder of the fleeting nature of ill-gotten gains. The Holy One, blessed be He, has said that even for a brief moment, the wicked will enjoy their own pleasures in this world and then they and their helpers will descend to Gehenna. Gehenna, often translated as hell, is more accurately understood in this context as a place of purification, a place where the consequences of our actions are fully realized.

And it's not just about personal morality, either. The Midrash points to the story of Esau, the brother of Jacob, as an example of wickedness exposed. As it says in Jeremiah (49:10), "For I have stripped Esau bare; I have uncovered his hiding places." The prophet is saying that Esau's true nature, his self-serving ambition, will eventually be revealed.

David, King David himself, understood this principle deeply. "I will not eat at their table or sit among them," he declared. He drew a line. He understood that associating with the wicked, even in seemingly harmless ways, could compromise his own integrity and ultimately lead him astray.

So, what does this all mean for us today? It's a call to examine our own choices, our own allegiances. Are we drawn to those who seem powerful, those who promise quick rewards? Or are we willing to stand with the oppressed, to embrace humility, even when it's difficult? The Midrash Tehillim reminds us that true and lasting happiness is found not in fleeting pleasures or self-serving alliances, but in acts of compassion, and in a life lived with integrity. It's a choice we all face, every single day. And the answer, according to this ancient wisdom, is clear.