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Rashi the Vintner
as the legend of Rashi the vintner is, Haym Soloveitchik, a professor at Yeshiva University and the leading contemporary historian of Halachah, or Jewish law, argues against it.
In his 1978 essay “Can Halakhic Texts Talk History?” Soloveitchik argues that: “Jewish communities were generally tiny, averaging from a handful to a score of families and tended (in the Champagne region) to make their own wine… [which] was usually produced anew every fall… It is difficult to see how this could have been accomplished without the concerted effort of the entire community.”
Thus, he argues in a footnote, Rashi’s clear familiarity with wine production — as evidenced by his Jewish legal writings and Talmudic commentary — owes more to his having been a posek (a halachic decisor) for his small community, than to the prospect that he actually earned his living through wine.
As Soloveitchik put it, “the presumption is against anyone being a winegrower in Troyes” because the “deeply fissured soil to this day is inhospitable to viticulture.”
He allows that Rashi’s wording at times implies that there were some privately held vineyards, but almost certainly nothing productive enough for a family to earn a living off its wine.
“Despite all this,” Soloveitchik concludes, “Rashi may have been a vintner; but by the same token he may have been an egg salesman.”