Wealth — Eruvin 86a
תלמוד בבלי מסכת עירובין דף פו/א
רבי מכבד עשירים רבי עקיבא מכבד עשירים
It is obviously difficult to understand why R' Yehuda HaNasi and R' Akiva would give honor to wealthy people. Could it be that they honored wealthy individuals merely because of their wealth?!
Teshuvos HaGeonim (Musafia-Lik §2) explains that there is a category, separate and distinct from a Talmid Chacham, of a Ba'al Ma'asim, a person who gives Tzedakah and involves himself in communal needs graciously, and who possesses stellar character traits. Such people deserve respect even if they lack wisdom. Indeed, if they are Yi'ri'ei Cheit, they are superior to Talmidei Chachamim (see Shabbos 31b). It was this type of wealthy individual that Rebbe respected.
Maharil (Minhagim, Likutim §35) in the name of Maharam Segal explains that since R' Yehuda HaNasi was very wealthy, he accustomed himself to give honor to other wealthy individuals so that people would honor him for his riches as well, and not for his Torah wisdom, as he did not want to make the crown of Torah a diadem with which to enhance his prestige (R' Akiva honored the rich for the same reason).
The Kitzur Shulchan Aruch (29:3) explains that the reason to give honor to the wealthy is not because they necessarily deserve it, but as an exercise in humility: One should always strive to identify an aspect in which one's fellow man may be superior to oneself. In the case of a rich person, even if he lacks any other redeeming quality, one should be dan l'kaf zechus that he must have some superior merit for which riches were bestowed upon him.
[For other explanations, see Chasam Sofer to Gittin 59a d.h. Bunis ben Nunis, and the two different explanations given by R' Tzadok HaKohen of Lublin, in Pri Tzaddik to Matos §13 and in Likkutei Ma'amarim §16 d.h. Al Kein Amru Zal (Menachos 29a).]