(Mishnah): If they poured him the cup (of wine for Kiddush), he should say, "That which I will leave at the bottom of the cup is Maaser and what is near it should be the rest of the Maaser. That which I (first) made Maaser shall be Terumas Maaser for the whole Maaser and the Maaser Sheni should be at the mouth of the cup and should be redeemed onto money."

(Gemara): (The Mishnah seems to be referring to when they pour the cup on Friday night (not before Shabbos) and therefore he must be making this stipulation on Shabbos itself?) Rather, the Mishnah is merely teaching about a case of pouring the cup, but the stipulation is made before Shabbos.

What's the case? If the stipulation takes effect before he drinks, he will certainly be drinking a mixture that contains Maaser"! If he says, "When I will drink...", it turns out that he must have drank Tevel since the Terumah only comes into existence after the wine has been drank. Rather, he said, "When I will drink, the Maaseros should take effect retroactively.

Question: Isn't he thereby carrying Tameh Terumah (in his cup) on Shabbos?

Answer (R. Elazar): He leaves a small amount of Chulin (together with the Terumas Maaser, allowing to move them together) as a Mishnah teaches (in Maseches Shabbos), "One may carry Tameh Terumah together with Chulin".

Rebuttal: The two cases are incomparable - there, he is moving the Tameh for the sake of the Tahor; here, he is moving the Tahor for the Tameh!

Answer (R. Yosi bei R. Bun): He only makes it Terumah when it leaves the cup.

The later Mishnah teaches that one who buys wine from the Kusim (he should make a stipulation...). The Baraisa on that Mishnah teaches that R. Yosi and R. Shimon prohibit making this stipulation, lest the wine bottle split before he manages to separate, causing him to have drank Tevel retroactively. If so, our Mishnah does not follow R. Yosi and R. Shimon.

Rejection (R. Yaakov bar Idi): No, all agree here that it can be made, since he drinks it immediately afterwards.

(Mishnah): If a worker does not trust his boss (for Maaseros), he should take one fig and say, "This and the nine figs that follow it should be Maaser for the 90 that I will eat, but this one should be the Terumas Maaser for them and the last ones should be Maaser Sheni and redeemed onto the coins. He should deprive himself of one fig (so as not to cause a loss to his boss when he gives one as Terumas Maaser).

(Rabban Shimon ben Gamliel): He may not deprive himself, since he will be weaker and will reduce his work for his boss.

(R. Yosi): He does not need to deprive himself, because it is a stipulation of Beis Din that Terumas Maaser be given from the property of the boss.

(Gemara) (R. Eliezer citing R. Hoshiya): (The correct location of this entry is in Maseches Terumos Perek 4 Halacha 2. The Mishnah teaches that according to R. Meir, if an Am HaAretz's produce was in a storeroom and he gave a Se'ah to a Levi employee (as Maaser Rishon) and a Se'ah to a poor employee (as Maaser Ani), a Chaver employee separates up until 8 Se'ah and he may eat from them (without being concerned that they are Tevel, since he saw the boss tithe). R. Meir viewed every person like an employee who doesn't trust his boss.

Certainly, if the figs became burnt, the Terumah he declared is invalid and the mixture remains Tevel. And if the Terumah became burnt, when he eats the fruits, the Terumah is sancitified retroactively.

Question: What is the meaning of the term 'Chasach - save' in the Mishnah?

Answer: He should deprive himself of eating one fig and use it for Terumas Maaser.

Baraisa: One should not plow with his cow at night and then hire it out in the day. One should not work his own property at night and hire himself out in the day. A worker should not starve himself or afflict himself, because as a result, he will reduce his boss's work.

R. Yochanan went to a certain place and found that the schoolteacher was weak. He asked them what was going on and they said that the teacher often fasts. R. Yochanan told him that he may not fast. If one who hires himself out to do mundane work is not allowed to fast, certainly one who hires himself out do Heaven's work is not allowed to fast.

(R. Chiya bar Ashi citing Rav): (Explaining R. Yosi in the Mishnah) It is a stipulation of Beis Din that Terumas Maaser is taken from the worker and Maaser Sheni from the boss.