While some medieval Jewish exegetes explicitly set out to counter Christian interpretations of certain biblical passages, Rashi (1040-1105)—the most influential of them—only appears to have done so once, with a reference to the beliefs of the “sectarians.” Yedida Eisentstadt argues, however, that on several occasions Rashi offered implicit evidence against supersessionism, the belief of some Christian theologians that, because Jews rejected Jesus, they were sent into exile and lost their chosen status, which then passed to the Church.
Most illustrative, writes Eisenstadt, is Rashi’s commentary to Deuteronomy 4:25-26, which reads: “When you have begotten children and children’s children and are long established in the land, should you act wickedly and make for yourselves a sculptured image in any likeness, . . . you shall quickly perish from the land.” Rashi here, as he often does, cites an earlier rabbinic commentary, but rather than summarizing or quoting it directly, he expands upon it in a way that suggests a broader point:
Although the [biblical] passage sounds like a warning (if you do x, then God will do y), it can be understood as a prediction: once generations of Israelites are settled in the promised land, they will be led astray to worship forbidden images and thereby anger the Lord. . . .
According to classical Jewish theology, both Jewish exiles were a punishment from God. . . . After [the destruction of the First Temple and] the first exile, God allowed Israel to return to the land and rebuild the Temple. The second exile [at the hands of Rome] is meant to last until the messianic age, after which the people would return to the holy land as they did after the end of the first exile. But Christian theologians offered a different understanding of the exile. In light of Deuteronomy’s theology of reward and punishment—and passages like the one above that threaten divine rejection—ancient and medieval Christians interpreted the writings of the apostle Paul and historical events to bolster their claim that they are God’s new covenantal people. . . .
In his comment on Deuteronomy 4:25, Rashi may have been responding to Christian interpreters who viewed the Hebrew Bible through supersessionist eyes. Reading the threats in Deuteronomy as referring to the permanent exile after the destruction of the Second Temple, Christian exegetes interpreted this exile as punishment for the Jewish rejection of Jesus as messiah. By [citing the talmudic teaching that] Moses’ prophecy in these verses was [fully] realized in the first, Babylonian exile, Rashi subtly suggests that the prophecy cannot refer to the subsequent Roman destruction and exile, which, according to Augustine, was emblematic of God’s rejection of the Jews. Moreover, if God brought on the Babylonian exile early in order to avoid having to fulfill the promise of destruction, [as Rashi claims], then God never did and never will abandon Israel.
Read more on theTorah.com: https://thetorah.com/does-rashis-torah-commentary-respond-to-christianity