Devarim Rabbah, a collection of rabbinic teachings on the book of Deuteronomy, dives right into this thorny issue. It all starts with a verse from Job 34:30: “He prevents a deceitful person from reigning, from setting hindrances [mokeshei] for the people.” The word mokeshei is particularly interesting. It means "hindrances" or "snares," but Rabbi Yoḥanan and Reish Lakish offer a striking interpretation. Rabbi Yoḥanan argues that if you see a wicked person leading the generation, it’d be better if everyone just flew away! The text connects mokeshei to the idea of flying, referencing Amos 3:5: "Will a bird fall into a trap on the ground, and there is no snare [mokesh] for it?" In other words, a bad leader is a trap, and escape is the only option.

But what about trusting in leaders in general? The Rabbis in Devarim Rabbah don't hold back. When the Israelites demanded a king, essentially rejecting God's direct rule, the Holy One, blessed be He, responded, "Did you not forsake Me and request a king for yourselves?" It’s a pointed question, highlighting the inherent risk of placing faith in human leadership. The text then quotes Psalms 146:3: “Do not trust in princes…” Ouch.

Rabbi Simon, quoting Rabbi Yehoshua ben Levi, takes it a step further. He says that anyone who trusts in God merits to be comparable to Him. They become, in a sense, Godly. The proof? Jeremiah 17:7: “Blessed is the man who trusts in the Lord, and the Lord is his haven.” But the flip side is also true. Those who trust in idols, in false gods, become like those idols, as Psalms 115:8 warns: “Those who make them will be like them.” It's a powerful statement about the transformative power of faith – for better or for worse.

And what about trusting in regular, flesh-and-blood humans? The Rabbis are blunt: their protection is fleeting because humans are fleeting. Psalms 146:3 says it plainly: “In man, in whom there is no salvation.” The verse continues, "His spirit departs; he returns to his earth." We are mortal.

The text reveals a divine frustration. God says, "They know that a flesh-and-blood human is nothing, yet they forsake My honor and say: 'Install a king for us.'" It's a cry of disappointment, followed by a chilling prophecy: "By your lives, ultimately you will feel what is destined to befall you under your king." This echoes Hosea 7:7: “All their kings have fallen; no one among them calls to Me.” They put their faith in flawed humans, and when those humans fail, they have no one to turn to.

So, what are we to make of all this? Are we doomed to a cycle of disappointment in our leaders? Perhaps the message isn't to avoid all leadership, but to be discerning in where we place our trust. To remember that even the most powerful figures are still just human, and that true and lasting support comes from something far greater. Food for thought, isn't it?