This sheet on Deuteronomy 7 was written by Avidan Freedman for 929 and can also be found here
Sometimes I yearn for the simple clarity of the life described by the Torah. If you're good, you get rewarded- children, produce, livestock, the works. These are the promises Moses opens chapter 7 with. And if you're bad, you get punished: plagues, wars, exile. It would be so much easier to know if you're on the right path if you could constantly get instant Divine feedback.
But real life doesn't work that way, and the commentators already began to highlight the complexity by reading between the lines. On the phrase "He repays those who hate Him to his face, to destroy him," (“who instantly requites with destruction those who reject Him”) the Targum explains that God actually gives evil people a good lot in this life, so that they will not have any merits left in the world to come, so that if you look at who's enjoying blessing in this world, you can't know whether it's because they're so good or so bad. On the words 'that I command you to do today," the Gemara explains that 'today' you do them, but only in the unknowable world to come will you receive the reward, so that if you look at who's suffering in this world, you still can't really know anything about their righteousness or sinfulness.
But is this situation really more complicated, or is it perhaps simpler? To act with the constant expectation of divine reward or punishment is to be in a child-like state of constantly testing boundaries with God- what will He do now, how will He react to this? This is what the end of chapter 6 refers to when it forbids 'testing' God. It's a tiresome game which is the exact opposite of the command 'be pure/wholesome (tamim) with Hashem your God' (Deut. 18).
The Ramban explains that the word 'ekev' means twisted, roundabout (a root which gives us the name Ya’akov, Jacob). When a person is constantly looking for explanations, it takes him around and around (mi'saviv) to find the reason (siba). The opposite of 'ekev' is 'yashar', to be straight with God, not to look for the 'why', but rather to focus on the 'what'. 'Walk before me and be tamim', God commands Abraham.
Rather than a crooked, convoluted path marked by impossible guesswork of the divine will, God wants us to walk the straight path dictated by our convictions. It is the path not of Ya'akov, but of Yisrael.
Rabbi Avidan Freedman is the Rabbi of Hevruta, the Shalom Hartman Institute's post high school program for Israelis and North Americans, and an educator in the institute's high school.
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