A Jew is prohibited from tattooing himself. If a person with tattoos were to convert to Judaism, would they be required to have the tattoos removed?
Would a Jew who got a tattoo and later repented be required to have it removed?
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According to this article by Rabbi Dr. Ari Zivotofsky there is no requirement to remove a tattoo, although it could be considered a pious act to do so, especially if the tattoo depicts something immoral and idolatrous.
He discusses four ways of removing a tattoo, two of which are permissible, and two of which are questionable. Removal via a cream or laser surgery are permissible. However removal via injecting new dye or via plastic surgery are questionable, due to issues of tattooing and wounding ones self, respectively.
While there is a commandment for a Jew to not get a tatoo, Leviticus 19:28, B.T. Makkot 21a there is, however, a separate Torah prohibition - "Lo Yosif" - not to inflict a wound upon yourself, Deuteronomy 25:3. According to many poskim, removing a tattoo involves "wounding" yourself. Therefore, it is generally prohibited to a Jew to inflict pain upon himself in order to remove the tatoo. This is why you see many Jewish survivors of the death camps still wearing the numbers that the Nazis tatooed on their arms. Rabbi Hanoach Teller, in his book, "It's a Small World," tells a nice story about a Jew who had become a baal tshuva and went to a men's mikvah, but was embarrassed to show his naked body with many tatoos. An older man broke the silence and, showing him the numbers on his forearm, said, "see, I have a tatoo, also." Based on this, and the fact that a good friend of mine, Dr. Clifton Price, zt'l, a ger tzedek of amazing merit, who had a tatoo that described him as "Slim," I see no basis for denying conversion to a person because he had a tatoo when he was not Jewish.
There are sources that say it is permitted to have a tatoo removed, however. Rabbi Moshe Feinstein, zt'l, held that a young woman who wanted to increase her marriage prospects was permitted to undergo cosmetic surgery although she would be causing wounds to be inflicted on her. He permitted it, since the surgery is done with her will and is essentially for her good. Iggrot Moshe, Choshen Mishpat 2:66. The Talmud, Taanis 23b, relates an incident where one of the Sages lifted up his frock when walking through thorns. "Skin heals, clothes don't," said the Sage. Even though he was scratching his skin by walking through the thorns, it wasn't done in a hostile or degrading manner. Rabbi Feinstein cites this, and a ruling by Maimonides, Rambam, Hilchot Chovel U'Mazik 5:1, as coroboration of his ruling.
According to this article, Rav Eliyahu Bakshi-Doron (Techumin 22:387) viewed the removal of a tattoo as a meritorious act to avoid remembering a previous sinful life. However, Dayan Weisz (Teshuvot Minchat Yitzchak 3:11) does not (seem to) agree that this is necessary. (This is aside from the opinion of Rav Ephraim Oshry (Teshuvot Mee’ma’makim 4:22) that Holocaust survivors should not remove their tattoos (which may have a unique status).
All citations are found in the linked article. I have not looked up any sources inside.
Rav Moshe Heinemann said in a shiur in Ner Yisroel to answer such a question "No, he is not obligated to remove a tattoo he received earlier. The torah doesn’t say you cannot have a tattoo – it only says you are not allowed to make a tattoo on your body (Vayikra 19:28 - וְשֶׂרֶט לָנֶפֶשׁ לֹא תִתְּנוּ בִּבְשַׂרְכֶם וּכְתֹבֶת קַעֲקַע לֹא תִתְּנוּ בָּכֶם אֲנִי ה)"