Though Rashi usually explains the Torah, sometimes it seems like he contradicts it. An excellent example can be found in Devarim 12:28: “Observe and hear all these words which I command you, that it may go well with you and with your children after you forever, when you do that which is good and upright in the eyes of Hashem your G-d.”
The Torah describes its mitzvos as tov ve’yashar, good and upright, in the eyes of Hashem your G-d. What is the difference between tov and yashar? Rashi says that tov means in the eyes of Hashem while yashar means in the eyes of man. The problem is that this directly contradicts the pasuk which says that the mitzvos are “tov and yashar in the eyes of Hashem” – meaning, yashar is also in the eyes of Hashem and not, as Rashi interprets, in the eyes of man.
To address this type of question, it’s often a good idea to temporarily ignore the contradiction and identify the lesson Rashi is trying to convey. To do so, we should understand how Rashi is interpreting the Torah’s claim that the mitzvos are good and upright.
Rashi says that tov means good in the eyes of Hashem. This is seemingly based on the first few times the Torah uses the term tov. After completing each of the six days of creation, it says, “And Hashem saw that it was tov.” Here too, Rashi interprets the statement that the mitzvos are tov to mean that they further Hashem’s objective in creation; they facilitate creating the type of society that Hashem intended.
Rashi then says that yashar means upright in the eyes of man. The lesson is that the Torah isn’t like ascetic religions which are good for their gods but bad for their followers. Instead, the Torah maintains that there’s a synergy between that which is good in G-d’s eyes and that which is upright in man’s eyes.
Putting tov and yashar together, Rashi is interpreting this pasuk as teaching that the Torah carries out Hashem’s plan (tov) in a manner that is simultaneously in line with man’s judgment of a good way of life (yashar). As the pasuk in Mishlei 3:17 says, “Her ways are pleasant and all her paths are peace.”
Let’s now return to the contraction. How can we reconcile the fact that the pasuk says that the mitzvos are both tov and yashar are in Hashem’s eyes while Rashi says that yashar refers to the way man views the mitzvos?
To answer this question, let’s probe Rashi’s claim that the mitzvos are upright in man’s eyes. Is this really true? After all, Chazal tell us that Yishmael and Edom took issue with certain mitzvos (see Rashi to Devarim 33:2). Even nowadays, many are critical of various mitzvos. Some find the laws of Shabbos or kashrus overly restrictive: others consider mitzvos like lulav or korbanos to be archaic. To claim that the mitzvos are upright in man’s eyes, we must ask, which man?
Perhaps the answer emerges from Koheles 7:29: “G-d made man upright (yashar) but they search for many (corrupt) strategies.” The point is that Hashem made man bi’tzelem Elokim, enabling him to have a sechel hayashar, a straight sense of right and wrong. Unfortunately, many pervert this sense and instead embrace the sense of right and wrong that’s grounded in their desires and fantasies. But the open-minded person who hasn’t perverted his G-d-given nature will judge the mitzvos as being yashar. This is attested to the description of the mitzvos in Devarim 4:8 “For this is your wisdom and your understanding in the sight of the peoples, who shall hear all these statutes, and say, ‘Surely this great nation is a wise and understanding people.’”
We can now see how Rashi isn’t contradicting the original pasuk but complementing it. Rashi is telling us that the plain meaning of yashar is that the mitzvos are upright in man’s eyes. But the pasuk is conveying the fact that man’s eyes are only valuable insofar as they see what is yashar in Hashem’s eyes – that they are in line with man’s G-d-given sense of yashrus.