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Why does the blessing of wine in Bereishis 27:28 spell "tirosh" two ways, and what does it mean that one who merits becomes a "rosh" (head) while one who doesn't becomes "rash" (impoverished)? The shiur develops a yesod that fulfillment exists only commensurate with sensing lack—a person can only become what he recognizes he's missing. Without feeling the void of unfulfilled potential, there's no motivation to grow, and the absence itself becomes a form of bankruptcy.
Rabbi Zweig analyzes the blessing Yitzchok gave to Yaakov in Bereishis 27:28, focusing on the word "tirosh" (wine). The Gemara (גמרא) notes that this word appears in two spellings—sometimes with a vav (תירוש) and sometimes without (תירש). The Gemara interprets: "זכה נעשה רוש" (if one merits, he becomes a rosh/head), "לא זכה נעשה רש" (if one does not merit, he becomes rash/impoverished). Rabbi Zweig raises several difficulties with this teaching. First, why does failing to merit the blessing result in poverty rather than simply lacking the blessing's benefits? When other blessings are not fulfilled, the person simply doesn't receive the benefit—there's no opposite punishment. Second, what is the connection between leadership (rosh) and poverty (rash) as opposites? Third, why is this message specifically embedded in the word for wine?
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Bereishis 27:28
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