פירוש על תרומות 1:8

הזיתים הנכתשים – it was customary to crush olives in a mortar-shaped cavity to remove their oil.

Introduction This mishnah is a foil to mishnah four above, where we learned that one does not give terumah from an unfinished product in order to exempt a finished product. Here we learn that one also should not give terumah from a finished product for an unfinished product. However, the difference is that while Bet Hillel held in mishnah four that if he did give terumah, his terumah is not terumah, in today’s case if he did give terumah it is valid.

תרומתו תרומה – it is completed, from the Torah.

They may not give terumah from oil for crushed olives nor may [they give terumah from] wine for trodden grapes. One may not give terumah from oil or wine for olives or grapes that have begun to be processed but have not yet completed their processing, such as crushed olives or trodden grapes.

ויחזור ויתרום – from the perspective of the Rabbis, after he has completed the pounding of those olives and the treading of the grapes, he will go back and remove the priest’s due a second time according to the measure that is needed for oil and win that he has removed.

If he did so, his terumah is terumah, but he must give terumah again. Here we get a halakhah the likes of which we have not yet seen. On the one hand, if one does give terumah from finished produce for unfinished produce, his terumah is valid. However, he must go back and give terumah again for the wine and oil that are produced after he gave the first time.

הראשונה מדמעת – if it fell to less than one-hundred [parts] non-holy produce, everything is made subject to the law of Terumah through an admixture and it is prohibited to “foreigners” (i.e., non-Kohanim) and everything is sold to a Kohen – for it is complete priest’s due according to the Torah.

The first terumah renders on its own [produce into which it falls] “doubtful terumah” and is subject to the added fifth, but not the second. The first terumah is real terumah, while the second is not. The mishnah lets us know this by relating that if this terumah falls into other non-terumah produce, it renders the entire mixture “doubtful terumah.” A non-priest who accidentally eats such a mixture will have to repay the amount he ate, plus an added fifth. However, the second terumah that he separated is not terumah that the Torah mandated, and therefore, the penalties for it falling into regular produce is not enacted. This second terumah was only a penalty on the person for having separated terumah from unfinished produce on behalf of finished produce.

וחייבין עליה חומש – a foreigner (i.e., non-Kohen) who eats it inadvertently pays the principle and [an additional] one-fifth according to the law regarding all foreigners who eat priest’s due.

אבל לא שניה – because it is not other than a Rabbinic ordinance; therefore it is not eaten until priest’s due and tithes are separated from it from another placer, since from the Torah, it is completely produce that cannot be eaten until Levitical and Priestly gifts have been separated, and if you ask – what is the difference here when one separates priest’s due from [olive] oil instead of from pounded olives, that his separated priest’s due is priest’s due, and then separates priest’s due again and what is the difference above concerning one who separates priest’s due olives instead of [olive] oil and grapes instead of wine where his separation of priest’s due is not priest’s due? And one can say that regarding a person who separates priest due from olives instead of [olive] oil, where there is a loss to the Kohen, his separating priest’s due is priest’s due/Terumah, but that the Rabbis are they who decreed that he should go back and separate priest’s due once again.