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Say a person never gave charity, due to ignorance or whatever other reason. He has now become a Baal Teshuvah and started observing the Torah.

What is the halacha with charity? Does he have to give 10% of all his assets, 10% of everything he has ever made or just start from scratch and begin giving maaser with each new pay check?

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Well I would assume it depends if we hold its a doraisa,drabbanan or minhag these days,this is a three way machlokes. –  sam Jul 24 '13 at 18:07
    
Depends on: judaism.stackexchange.com/q/8846 –  msh210 Jul 24 '13 at 18:24
    
R' Moshe Shternbuch has a responsum about this very question. I don't have time to summarize it, maybe someone else can volunteer... –  Dave Jul 24 '13 at 20:56

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The Shulchan Aruch in Yoreh De'ah 249 סימן רמט - כמה חייב ליתן וכיצד יתננה says that the first year one decides to start keeping Ma'aser Kesafim, on separates 1/5 or 1/10 of one's capital.

After that, every year one separates 1/5 or 1/10 of the profit on one's income.

Since he starts with יִתֵּן עַד חֹמֶשׁ נְכָסָיו it would seem that he considers all one's assets as capital.

The entire Siman is:

א שִׁעוּר נְתִינָתָהּ, אִם יָדוֹ מַשֶּׂגֶת, יִתֵּן כְּפִי צֹרֶךְ הָעֲנִיִּים. וְאִם אֵין יָדוֹ מַשֶּׂגֶת כָּל כָּךְ, יִתֵּן עַד חֹמֶשׁ נְכָסָיו, מִצְוָה מִן הַמֻּבְחָר; וְאֶחָד מֵעֲשָׂרָה, מִדָּה בֵּינוֹנִית; פָּחוֹת מִכָּאן, עַיִן רָעָה. וְחֹמֶשׁ זֶה שֶׁאָמְרוּ, שָׁנָה רִאשׁוֹנָה מֵהַקֶּרֶן, מִכָּאן וָאֵילָךְ חֹמֶשׁ שֶׁהִרְוִיחַ בְּכָל שָׁנָה.

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