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Why does Rashi (רש"י) read "one who loves money will not be satisfied" as meaning he won't even spend money? The shiur develops Rashi's insight that people who define themselves by net worth cannot spend because every expenditure diminishes their identity. Only those with genuine self-worth (built through personal effort) can enjoy their wealth freely.
Rabbi Zweig begins by examining a puzzling commentary of Rashi (רש"י) on Koheles 5:9. The verse states "Oheh kesef lo yishba kesef" - one who loves money will not be satisfied with money. While the simple reading suggests the person spends but isn't satisfied, Rashi translates it as the person won't even spend (eat) the money. This seems contradictory to the verse's apparent meaning. To explain Rashi's approach, Rabbi Zweig introduces the Talmudic principle that "a poor person is like a dead person," specifically citing the story of Yaakov fleeing from Esav. When Eliphaz (Esav's son) finds Yaakov, he resolves the conflict by taking all of Yaakov's money, since being poor is considered like being dead. The key insight is that this applies specifically to someone who was wealthy and lost their money ("dal" - meaning to subtract), not someone who was always poor.
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Koheles 5:9
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Why do Jews give money for Chanukah while others give presents? The distinction reflects two opposing philosophies: Esav's "I have much" treats money as personal reward, while Yaakov's "I have everything" sees it as divine responsibility. Giving children money teaches judgment and accountability, while presents simply convey affection without developing character.
