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BH

Is it true that there was a sage on his death bed who said I wish I used up all my money?

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Reish Lakish, in Gittin 47a:

כִּי נָח נַפְשֵׁיהּ שְׁבַק קַבָּא דְמוֹרִיקָא, קְרָא אַנַּפְשֵׁיהּ: ״וְעָזְבוּ לַאֲחֵרִים חֵילָם״

When he passed away, he left a kav of saffron. He applied to himself the verse (Tehillin 49:11), "They leave their wealth to others."

Maharsha ad loc. cites in this connection Eruvin 54a, that "it is the way of fools" to want to make sure to leave an inheritance, so Reish Lakish regretted that he was doing so.

Ein Eliyahu ad loc. observes that there are other places in the Gemara where leaving an inheritance is seen as a positive thing to do. He notes that since Reish Lakish himself had been a bandit earlier in life (Bava Metzia 84a), he might have been particularly worried that his children might follow in the same path and misuse their legacy. Although he instead suggests that Reish Lakish figured that all of his possessions ought to go towards paying back his erstwhile victims (or, if they couldn't be traced, using the funds for public-works projects).

The Chofetz Chaim (cited here) offers yet another reason: the time he spent earning the money to buy that kav of saffron was, in retrospect, wasted.

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