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If fruits were picked by a Cohen for themselves and then someone else eats (with the Cohen's permission, of course), does the person still need to separate Ma'aser?

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Short answer: Yes.

Long answer: Firstly, a Cohen gets Teruma, not Ma'aser, technically. (Though in Ezra's time they could [also] be given Maaser.)

Secondly, all fruit grown in Eretz Yisrael is Tevel until tithed - i.e. all Terumoth and Maasrot or taken off - no matter who grows the fruit.

Therefore, Cohanim may not eat Tevel, even if they want to eat fruit from their own trees.

However, a Cohen can keep the Terumah he separates from the fruit he picks or grows. He needn't give it to other Cohanim.

Source: שלחן ערוך - יורה דעה סימן שלא - דין נתינתם באיזה מקום

קכג: כֹּהֵן אוֹ לֵוִי שֶׁמָּכְרוּ פֵּרוֹת תְּלוּשִׁים, קֹדֶם שֶׁתִּגָּמֵר מְלָאכְתָן, וְאֵין צָרִיךְ לוֹמַר אִם מָכַר בִּמְחֻבָּר, הֲרֵי הַתְּרוּמָה וְהַמַּעֲשֵׂר שֶׁלָּהֶם

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  • So could he theoretically separate the trumah, "give" it to himself, and then add it back to the original pile? Oct 11, 2015 at 14:22
  • Not really, as he has to make the Bracha אשר קדשנו בקדושתו של אהרן וצוונו על אכילת תרומה before eating it. Oct 11, 2015 at 14:47
  • He would have to also be Tahor to eat the T'ruma and probably isn't.
    – CashCow
    Oct 12, 2015 at 14:56

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