Avot238

1:
Rabbi Yonatan also lived in the second half of the second century CE. He was young at the time of the Bar-Kokhba débacle, and during the persecutions that followed the Roman victory he, together with some young colleagues, decided to try their luck in foreign parts. The midrash [Sifré, Re'eh 28] tells the story:

Actually, several of these sages did eventually settle down outside Eretz-Israel, but Rabbi Yonatan, who apparently was the youngest of the group, remained in Eretz-Israel for the rest of his life.

2:
Rabbi Yonatan was a student of Rabbi Yishma'el. Not the Rabbi Yishma'el of the two previous mishnahs, but of Rabbi Yishma'el the great protagonist of Rabbi Akiva. Rabbi Yonatan learned from his teacher the method for which he was famed, which involved the interpretation of the Torah in as naturalistic a manner as possible. Throughout his life he tried to propagate his teacher's method, even when the rival method of Rabbi Akiva was gaining ascendency. The Gemara [Ĥullin 70b-71a] tells us how on one occasion he tried to convince one of Rabbi Akiva's star students, Rabbi Shim'on ben-Azzai, to adopt the system of Rabbi Yishma'el. And he very nearly succeeded! At least he managed to get ben-Azzai to admit that he deeply regretted not having studied under Rabbi Yishma'el.

3:
The teaching of Rabbi Yonatan in our present mishnah is the only time his name is mentioned in the whole of the Mishnah! And, to be honest, the teaching chosen is not really representative of the greatness of heart of this under-rated sage. (This is probably an indication of the extent to which the school of Rabbi Akiva gained complete ascendency and almost totally eclipsed the school of Rabbi Yishma'el and those faithful to his method.) At first reading the teaching of our present mishnah seems to be nothing more than a pious platitude; and try as hard as one can that is probably how it will seem also after a tenth reading. It clearly does not reflect what we know to be the hard reality of life: we know of many great sages who died in poverty and we know of many wicked people who died in extreme wealth. Possibly we must understand this teaching of Rabbi Yonatan as an earnest exhortation not to permit circumstances of financial need deflect one from Torah observance.

4:
In order to do greater justice to the Torah of Rabbi Yonatan here are some other statements attributed to him:

Rabbi Yonatan was the original author of the teaching that one should desecrate Shabbat in order to save life (though the teaching is usually quoted in the language of later sources). He said: Torah [Exodus 31:16] says: 'The Israelites shall keep Shabbat, observe Shabbat throughout their generations'; but one may profane one Shabbat in order to preserve someone that he may observe many Sabbaths" [Mekhilta, Ki Tissa].

He also tried to redefine the term 'Am ha-Aretz' saying that it designates a parent who does not educate his children in Torah [Sotah 22a].

Concerning the teaching of Rabbi Yishma'el in Avot 236 Derek Fields writes:

With respect to your discussion of Rabbi Yishma'el's dictum that one who sits in judgement may be complicit in suborning perjury, I agree with your discussion of the p'shat [surface meaning] of this text. However, I think that this mishnah begs for some counterbalance to the harshness of Rabbi Yishma'el's pronouncement. The importance of establishing the rule of law is so fundamental, that it is the only positive commandment in the Noachide laws. Were we to take Rabbi Yishma'el's warning at face value, we might be unable to find people who are willing to take the risks inherent in being a judge. I think that we need to understand this Mishna as, an albeit harsh, cry for humility as the overarching quality that defines a judge, and indeed all of our leaders. We would do well to extend Rabbi Yisma'el's teaching to apply it to all of us who are tempted to judge others, whatever the context.

I respond:

I believe that the following mishnah, Avot 237, solves the difficulty raised by Derek along the same lines as suggested by Derek.