(Tosefta): If a sharecropper received from a gentile a wheat seeded field to harvest; vineyards of grapes to harvest for wine or olive groves to harvest for oil, he should first tithe the gentile's portion before he gives it to him.

Question: Our Mishnah taught that he received it before it was sown, so that the obligation to tithe came when it was in the hands of the sharecropper; but if he received it after it was sown, must he tithe...?

Answer (R. Chanina): It's referring here to one who receives it in Kablanus - the reason that he is exempt from tithing is to encourage sharecroppers to accept land, otherwise Eretz Yisrael will remain uncultivated; but here, he received it already sown.

(The Tosefta continues): If he received it to harvest and divide whilst still ears (before the obligation to tithe came), or to pick grapes and divide them in the baskets (whilst still grapes, before they were made into wine), or to pick olives and divide them in the baskets (before they were made into oil); he may give them as they are (without tithing).

(The Mishnah taught (above Menachos 2-1(c)) - R. Yehuda said - When is this (that the sharecropper does not need to tithe before he gives it)? When he pays (the owner with produce) from that same field and that same species; but if he pays from another field or from another species, he must also separate Maaser.) This means that from the same species but not from the same field or from the same field but not from the same species, he must first tithe and then give him.

Baraisa (R. Chiya): From that same field - whether from the same or from a different species, he gives Terumah and then gives to the owner. From a different field, whether from the same or a different species, he must first tithe and he can then give.

Question: In our Mishnah (that the words 'when is this' indicate that R. Yehuda is coming to explain the Chachamim), the Halacha follows R. Yehuda. And according to R. Chiya's Baraisa (that there is a dispute between R. Yehuda and Chachamim), the Halacha is like the Chachamim. But does R. Chiya disagree with our Mishnah?

Answer: Our Mishnah is discussing a place where it was common for barley to produce double the quantity of wheat. (And since it appears like he is paying a debt - because he had agreed to pay in wheat, but now that he is paying in barley, he is giving a larger quantity of produce; therefore, he must first tithe.) R. Chiya's Baraisa is discussing a place where they produce equal quantities (so it doesn't appear like paying a debt, and he need not tithe.)

Question: (The Mishnah taught (above Menachos 2-(d)) that one who received a field from a gentile in Chakirus, he should separate Maaser before he gives the gentile his portion.) Here (for a Jew's field) you said that he must first give Terumah and then give the owner; and there (for a gentile's field) you said that he must first give Maaser and then give the owner...?

Answer (Chevraya citing R. Yochanan): The Chachamim penalized (to require the sharecropper to tithe) when receiving a field in Chakirus from a gentile but not from a Jew.

Answer #2 (R. Ila citing R. Yochanan): The requirement to tithe is according to the letter of the law - but the Chachamim were lenient when receiving from a Jew.

Each opinion has a Baraisa to support him... (Note: The Vilna Gaon adjusted the text in the next two entries.)

A Baraisa that supports R. Ila - One who receives a field in Chakirus from a Jew - he must first take Terumah and then give (the owner). R. Meir says that he must take Maaser and then give.

The Gemara explains: The Rabbanan reason that the Chachamim penalized when receiving in Chakirus from a gentile but not from a Jew. R. Meir reasons that they also penalized when receiving from a Jew.

Question: Why penalize one who receives from a Jew? Rather, it can only be explained like R. Ila, that Rabbanan say that strictly speaking, he must tithe, but they were lenient when receiving from a Jew. And R. Meir says that they followed the strict law, even when receiving from a Jew.

A Baraisa that supports Chevraya - One who receives a field in Chakirus from a gentile, he must first take Maaser and then give (the owner). R. Shimon says that he must first take Terumah and then give (the owner).

The Gemara explains: Rabbanan say that they applied the strict law when receiving from a gentile, but not when from a Jew. And R. Shimon says that they didn't apply it even when receiving from a gentile.

Question: Why would they not apply it when receiving from a gentile? Rather, it can only be explained like Chevraya, that according to Rabbanan, they penalized when receiving from a gentile but not from a Jew. And R. Shimon says that there is never a penalty given at all; therefore, if the gentile later converted or sold the produce to another Jew, he would need to give Terumah but not Maaser.

Question: (The Mishnah (Menachos 2-1(e)) taught from R. Yehuda that the law of first taking Maaser and then giving to the owner applies even if a person receives his own ancestral land from a gentile.) According to R. Ila, it is understandable; but according to Chevraya, who said that they penalized when receiving from a gentile, what would it help if he later converted or sold it to others, since the penalty is already resting upon it...?

(R. Yochanan): The Mishnah's case is when his ancestral field was forcefully taken by bandits - Chachamim required him to tithe when he receives it from the gentile, since it will encourage him to force himself to redeem it.