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1) [line 1] SHOKEL LO (SHEKALIM)
(a) In the Beis ha'Mikdash, many public sacrifices were offered (for example the daily Temidim, the Korbenos Musaf of Rosh Chodesh and the festivals, etc.). In order to finance these Korbanos, one half a Shekel was collected from every Jew, both those living in Eretz Yisrael and in the Golah, once a year.
(b) The half Shekalim were collected before Rosh Chodesh Nisan so that the Korbanos of the new year (which starts with the month of Nisan) would be offered from the money that was collected for the new year. On the first of Adar, Beis Din announced that the Shekalim should be collected, in order to ensure that all of the Shekalim would be collected before Rosh Chodesh Nisan (see Insights to Shekalim 2a). Some commentaries contend that a portion of the Shekalim would not arrive until after Rosh Chodesh Nisan, while others claim that all of the Shekalim arrived by Rosh Chodesh Nisan, since the Shekalim were collected from the regions further from Yerushalayim earlier in the year. (This latter opinion appears to be the conclusion of the Yerushalmi, Shekalim 2a - see Mishnas Eliyahu ibid. 2b.)
(c) The amount that was collected from each Jew was not fixed at half a Shekel. Rather, the amount given was always half of the "Matbe'a ha'Yotzei" (the primary coin in use at the time), provided that it was not *less* than the value of half a Shekel.
(d) The word "Shekel," as used in the phrase "Machatzis ha'Shekel," refers to the Shekel that was in use at the time of Moshe Rabeinu, which was equivalent to the "Sela" of the times of the Gemara. Machatzis ha'Shekel is half of a Sela, or two Dinarim. People became accustomed to calling the coin that was valued at half of a Sela, "Shekel," since it was "paid out" ("Shoklim" Oso) in order to fulfill the Mitzvah of Machatzis ha'Shekel each year (RAMBAN to Shemos 30:13).

*2*) [line 4] MITZVAH KA'AVID - (a) Even a person who did not send in his yearly Shekel still has a portion in the Korbenos Tzibur. Therefore he did not gain anything from the fact that someone paid his yearly dues for him. (The Gemara is apparently discussing a situation in which for some reason Beis Din is not taking a collateral from this person for not paying his dues.) -- RASHI; (b) The Gemara is discussing a person who already sent his Shekel to Yerushalayim, but the Shekel was lost or stolen before reaching its destination. Since he does not have to send in another Shekel, the person who sent in a second Shekel for him did him no favor -- TOSFOS DH v'Al.

3) [line 4] TORMIN (TERUMAS HA'LISHKAH)
(a) Every year, one half a Shekel was collected from every Jew to fund the Korbenos Tzibur that were offered in the Beis ha'Mikdash. Beis Din placed the money that was collected in a room in the Mikdash reserved for that purpose (see Background to Yoma 55:7, "Shekalim").
(b) At three times during the year (before each of the three festivals), Beis Din filled three boxes, each of which held three Se'in (approximately 21.6, 25 or 43.2 liters, depending upon the differing Halachic opinions) with Shekalim from that room. The portion that was set aside in the boxes was called the "Terumas ha'Lishkah," while the remainder of the Shekalim were called "Sheyarei ha'Lishkah" (Shekalim 7b, 8a). (See Insights to Shekalim 9:2)
(c) There is a difference of opinion as to why the Terumas ha'Lishkah was done three times a year rather than just once. One opinion states that the reason was only to publicize the Terumas ha'Lishkah (Shekalim 2b, see Insights there). According to others, Beis Din was concerned that the Terumas ha'Lishkah should be collected from the Shekalim that arrived later in the year (this opinion is also mentioned in the Yerushalmi, ibid.).
(d) The Shekalim from the Terumas ha'Lishkah were used to purchase the animals needed for public sacrifices and for the wages of certain laborers and appointees of Hekdesh. The Shekalim from the Sheyarei ha'Lishkah were used to buy other goods necessary for the upkeep of the Mikdash and the entire city of Yerushalayim (Shekalim 4a-b).

4a) [line 5] HA'AVUD - Shekalim that have been collected but have been lost
b) [line 5] HA'GAVUY - Shekalim that have been collected but are still on the way to the Beis ha'Mikdash
c) [line 5] HE'ASID LIGAVOS - Shekalim that have not yet been collected

5) [line 7] KAMISHTARSHEI LEI - he profits from it by being released from a monetary debt

*6*) [line 8] HA MANI? CHANAN HI - that is, according to Chanan the person who paid the Shekel for him cannot claim compensation in court. Therefore, even though the person for whom the Shekel was paid benefited from the Shekel, it is considered no more than a Grama, an indirect benefit, which is permitted -- TOSFOS DH Ha

7) [line 1] KISUFA MI LEIS LEI!? - does he not have shame (if he passes before the person who lent him money and he has not paid back the debt)?!

8) [line 15] KANKANIM - [empty] jugs, utensils in which wine is stored
9) [last line] PASHAT LO ES HA'REGEL - (a) he stretched out his foot to him scornfully, as if to say "take the mud off my feet" (RASHI); (b) he stretched out his foot to him hopelessly, as if to say "you can hang me from a tree by my leg and I still will not find the money to give you" (RASHI, second explanation); (c) he ran away to a distant place (RAMBAM, RITVA)

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