Understanding Anavah

(יב,ג) פְּנֵי הָאֲדָמָה-אֲשֶׁר, עַל ,מִכֹּל, הָאָדָם--וְּהָאִיש מֹּשֶׁה, עָנָו מְּאֹּד

The final line of the Mishna states that from the time when Rabbi Yehuda HaNasi died, humility and fear of sin ceased. Rav Yosef said to the tanna who reviewed the Mishna: Do not teach that humility ceased, for there is still one who is humble, namely me. Rav Nachman similarly said to the tanna who reviewed the Mishna: Do not teach that fear of sin ceased, for there is still one who fears sin, namely me. (Sotah 49b)

This Gemara (and Moshe who put the Torah into written format) is very questionable since this is not the style of the Chachamim to speak in a apparently boastful manner expounding their virtues. This appears to be the opposite of a humble person. Fortunately, we can find many commentators that provide approaches to understanding of this apparent contradiction.

1. To avoid teaching an incorrect text, these rabbis stated that the middos of Anavah (humility) and Yiras Chet (fear of sin) did not cease with the death of Rebbe Yehuda haNasi since there were still individuals in that generation after Rabbi Yehuda that still had these middos. (Maharsha)
2. Perhaps Rav Yosef and Rav Nachman did not take pride in themselves for their attributes of Anavah and Yir'as Chet in general. Rather, they sought to teach to the their Talmidim the extent to which the attributes of Anavah and Yir'as Chet are supposed to be applied. They intended that their Talmidim learn about these Midos from their own particular deeds. The Gemara in Berachos (64a) and Horayos (14a) relates that when the Rosh Yeshiva passed away, Rav Yosef was selected to be the new Rosh Yeshiva, but he declined and offered the position to Rabah instead. In order to teach his Talmidim how to conduct themselves, he pointed out his own willingness to decline such a great and prestigious honor. The Gemara in Gitin (31b) relates that Rav Nachman bar Yitzchak refused to honor the wealthy and powerful members of the family of the Reish Galusa, because he did not consider them to be worthy of honor. (Rashi in Megilah 28b explains that Rav Nachman mentioned by the Gemara here is Rav Nachman bar Yitzchak.) Although the Gemara in Sotah (41b) teaches that one is permitted to give honor (Chanufah) to a wealthy Rasha in this world, Rav Nachman was a Yerei Chet and refused to honor Resha'im even when doing so is permitted. He wanted his Talmidim to know that he did not act in this manner simply because his personality was such that he respected nobody. He therefore prided himself publicly for demonstrating Yir'as Chet, the fear of sin, in his deeds, so that his Talmidim would learn and follow in his G-d-fearing ways. (Ben Yehodia)
3. In the Yeshulayim Gemara there is an Amora with the name of אנא (which is usually translated as me). Thus, these two Amoraim were not talking about themselves. (Vilan Gaon)
4. There are different levels of Anavah. The Mishhan speaks of the level of Rabbi Yehuda that leads to Yiras Chet, Rabbi Yosef is pointing out that one should not conclude that Anavah no longer exists, since he has a lower level of Anavah, which does not lead to Yiras haChet. (HaDivrei Shaul)
5. There are different levels of Anavah. The higher level is the essence of Anavah and a lower level which is achieved by logic and reason. The explanation is that the humility of Moshe and of Rebbi was not based on logic, but rather it was an essential humility. (Rav Nachman was among the pious of Babylonia, and studied in the style of Babylonia, which, as explained in Chassidus, reaches the level of Kesser. Rav Nachman therefore refers to essential humility which derives from kesser ). This distinction explains how Moshe was humble (despite prophecy being a gift from above that cannot be developed by the person) -- Moshe possessed essential humility (which is not based on any reason). (Lubavitcher Rebbe)
6. Rabbi Yehuda haNasi had many highly-positive attributes. Rabbi Yosef and Rabbi Nachman who each had one each of such refined attributes, did not wish to be honored and compared to Rabbi Yehuda. So each one requested that the Tanna who reviewed the Mishnah should remove that attribute to avoid being compared to Rabbi Yehuda (Binyan Tzion)
7. Anavah is not denying the true accomplishments one has achieved. Rather one must understand what one has attained. Moshe Rabeinu received the Torah from fire and was declared to be a Prophet that would have no equal. The Anavah of Moshe was to believe that if someone else had be given the same tools and potential, that person might have achieved an even higher level. ((Amek haDavar)
8. The Mishnah was not proposing that Anavah and Yiras Chet had were completely removed from the world with the death of Rabbi Yehudah. Rather, Rabbi Yehuda sparked and lead many of his generation to also reach such levels. Each Amora thought that since they obtained one attribute that was mentioned in the Mishnah, then many others of their later generation also obtained that attribute, and thus, the attribute should be removed from the Mishnah. These Amoraim did not observe that they were unique in their generation, and thus, the attributes were not widespread in their generation. (Sefas Emes)
9. The intention of the Mishnah is that both attributes would no longer reside in one person. Thus, Rabbi Yosef and Rabbi Nachman reinforced that the Mishnah does not mean that both attributes are totally nullified, since each Rabbi still had one of the Attributes (HaToras Hakenuos)
10. The intention of the Mishnah is not that due to the greatness of Rabbi Yehuda were these attributes removed. Rather, due to the greatness of Rabbi Yehuda still having great pains and sickness in life, others fell his pain yet respected him for his achievements and achieved their own levels of humility and fear of sin. Thus, Rabbi Yosef (became blind and forgot much of his teachings) and Rav Nachman (who had to constantly fight his nature) exemplified the same ability to inspire others to achieve this lofty attributes (Nachalas Yaacov)
11. Similar to the statement, “And Shem said, I forgive as you requested. (Bemidbar 14,20). Why add as you requested? If the argument put forward was acceptable, it does not matter that you requested. Rather, the word of a Tzadik makes an impression in the world, that HaShem decreed that He would implement the word stated by the Tzadik. Thus, after the Mishnah was taught that upon the death of Rabbi Yehudah the attributes would be removed from the world, Rabbi Yosef and Rabbi Nachman stated that the attributes cannot be removed, since the people of the world still needed these methods of refinement of their lives. Thus, as Tzadikim they declared their opposition so that HaShem would agree and not remove these attributes from the world (Tepuchai Chaim)

Many editions of the Gemara Sotah end with the famous saying of Rabbi Pinchas ben Yair (which forms the outline for the Sefer Mesilas haYesharim (Path of the Just)

Rabbi Pineḥas ben Ya’ir would say: Torah study leads to care in the performance of mitzvot. Care in the performance of mitzvot leads to diligence in their observance. Diligence leads to cleanliness of the soul. Cleanliness of the soul leads to abstention from all evil. Abstention from evil leads to purity and the elimination of all base desires. Purity leads to piety. Piety leads to humility. Humility leads to fear of sin. Fear of sin leads to holiness. Holiness leads to the Divine Spirit. The Divine Spirit leads to the resurrection of the dead. And piety is greater than all of them, as it is stated: “Then You did speak in a vision to Your pious ones” (Psalms 89:20).

Why does the Gemara add this saying, which original location is Avodah Zara 20b?

Maharasha states that these 10 attributes were attained by the earlier Chachamim and were batel (removed) after the destruction of the Bais haMikdash and the deaths of the other mentioned Chachumim.

The Kol haRamaz offers an opinion that this saying of Rabbi Pinchas ben Yair was to provide hope to our generations that we still have the ability to obtain these high goals.