The monkey wrench in all this is the pasuk in last week’s parsha, “…ki ta’aseh hatov v’hayashar b’eini Hashem Elokecha.” (12:28) Why here does the Torah put tov before yashar? Rav Filber notes this problem in parenthesis and just says “yesh l’chaleik” but offers no hint as to what he had in mind.
I found the Ksav Sofer asks this question. The pasuk in Va’Eschanan, “v’asisa hayashar v’hatov,” tells us the ideal of not only doing right, “yashar,” but going “lifnim m’shuras hadin,” doing “tov.” One might be tempted to simply aim to do right – there is no requirement, after all, to go above and beyond the letter of the law. Yet, the Torah knows human psychology and recognizes that this approach is doomed to failure. As I tell my children all the time, if you aim to give 100%, you probably will end up with something like 75%. It’s giving 125% that will give you 100%. We all fall short of what we aim for – that’s life. The pasuk in Re’eh tells us “ki ta’aseh ha’tov,” if you aim to go above and beyond the letter of the law and strive for tov, “v'hayashar b’eini Hashem Elokecha,” then you will at least end up fulfilling the letter of the law in G-d’s eyes.
My wife suggested another answer on Shabbos that I really like and that is perfect for inyana d’yoma. The pasuk in Va’Eschanan that speaks of “yashar v’tov” is addressing the individual. On a personal level, one is obligated to give first priority to acting ethically toward others, even if that doesn’t make things “tov” or easy for oneself. The pasuk in Parshas Re’eh is speaking to the nation, and in particular note the pesukim that follow speak of the conquest of Eretz Yisrael. In that context we are obligated to first do that which is “tov,” that which is good for our needs as a people. What is yashar in the eyes of the world is a secondary concern, as the Jew-haters out there will never be satisfied, no matter how careful and ethical our behavior is.