Historically, how did Esav come to be associated with Rome/Christianity? How did Yishma'el come to be associated with Arabs/Islam?
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The Arabs were already associated with Yishmael at the time that Onkelos the Convert wrote his translation of the Torah. Although the same association is used in Targum Yonason Ben Uziel who lived two generations earlier (maybe even three!) he may not be the actual author of that translation and it may actually date from some time after the founding of Islam. See Parshas VaYeshev 37:25.