Our Gemara on Amud Aleph discusses a judgment that people seem to have when comparing the wealthy to the impoverished. In certain halachic/legal situations, there is an assumption that the borrower trusts the lender’s financial assessment but not the reverse; the lender does not trust the borrower. One reason given for this by the Gemara is that people assume God would not have rewarded this man with wealth unless he was trustworthy. Conversely the pauper's financial status is a punishment for his dishonesty. As it states in Mishley (11:3):
תֻּמַּ֣ת יְשָׁרִ֣ים תַּנְחֵ֑ם וְסֶ֖לֶף בֹּגְדִ֣ים (ושדם) [יְשָׁדֵּֽם]׃
The integrity of the upright guides them; the deviousness of the treacherous leads them to ruin.
This simplistic formula of status in this world as an indicator of spiritual attainment is not the full story. Quite the opposite: The Gemara (Pesachim 50a) gives us one sage’s account of the World to Come, after a near-death experience:
Rav Yosef, son of Rabbi Yehoshua ben Levi, who became ill and was about to expire. When he returned to good health, his father said to him: What did you see when you were about to die? He said to him: I saw an inverted world. Those above, i.e., those who are considered important in this world, were below, insignificant, while those below, i.e., those who are insignificant in this world, were above. He said to him: My son, you have seen a clear world.
Aside from the Gemara’s eyewitness report, common experience has also taught us that while there are many generous and worthy philanthropists, there also are noble and honest poor persons, and for that matter, unworthy tycoons. So, what do we make of our Gemara?
A simple answer might be that our Gemara is discussing popular conceptions and beliefs, regardless if they are fair or true. But, there is more to this, because Gemara (Eiruvin 86a) tells us that it was the practice of Rabbi Yehudah Hanasi and Rabbi Akiva to show deference and esteem for the wealthy.
Maharil (Likkutim 35) explains that since Rabbi Yehuda Hanasi himself was wealthy, and Rabbi Akiva became wealthy later in life, they both honored affluent people as a tactic to avoid receiving honor for their Torah knowledge. If they promoted the idea that wealthy persons deserved respect, the respect and adulation they personally received for their wisdom and piety would be less likely to make them arrogant. They could humbly fight against spiritual complacency by telling themselves that the respect was coming only due to their deep pockets, not any real virtue.
While this is clever, I think there is a logical problem with the explanation. If there wasn’t something intrinsically proper about showing honor to the rich, how could Rabbi Yehuda Hanasi or Rabbi Akiva falsely encourage such flattery? Is it ok to misdirect all Jews to show deference for the wealthy, even for the justifiable cause of forestalling arrogance on their part? I believe this question comes from not understanding the Maharil properly. He was NOT explaining why the populace should show respect; that was a given, that wealthy persons are deserving of additional respect. He was explaining why Rabbi Yehuda Hanasi and Rabbi Akiva felt compelled to honor a rich person, as they were wealthy too, and so relative to him, merely a peer. The Maharil is suggesting that Rabbi Yehuda Hanasi and Rabbi Akiva did it for themselves. They wanted to train their thinking that their honor was only for practical mastery of material matters, leaving them free to seek spiritual goals motivated only by piety and not a wish for fame and fortune.
Regardless, we are still left with a question why our Gemara and others seem to value giving the wealthy special consideration. Pesach Eynayim (Eiruvin ibid) suggests we see that all material benefits are considered a gift from God, as we even see how Yaakov went back to retrieve small forgotten flasks so as not to squander what God gave him. Therefore, a person endowed with wealth must be a worthy recipient and vessel for God’s blessing. While this proves the point, it does not answer it. How does such sentiment match up
with the idea expressed in Pesachim above, that in the world those who seem deserving of honor often are not, and vice versa?
I believe the simple answer is that we erroneously overstated the position of our Gemara or the Gemara in Eiruvin, by saying that, as a class, wealthy people are more righteous. That is not necessarily so. However, since God clearly favored them in the realm of money, they probably are trustworthy. Similarly, Rabbi Yehuda Hanasi or Rabbi Akiva showed honor for the wealthy because of the mitzvos that their wealth uniquely positions them to accomplish. This is not to say that they are presumed to be more righteous than the pauper across all character and moral traits.
Translations Courtesy of Sefaria, except when, sometimes, I disagree with the translation 
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