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It is a Mitzvah to rejoice on Chanukah. One is not to show any sadness on Chanukah and is rather to express joy over the miracle that Hashem performed for us. The joy which one must have on Chanukah is even greater than on Sukkos, and is similar to the joy of Simchas Torah, as both of these joys are a custom which are not written in the oral law.
The joyous occasion of Chanukah is to be utilized to increase in Torah learning. One is obligated to during Chanukah to learn Torah and pray with extra concentration, in light of the fact the Yevanim desired to uproot Torah learning and Avodah. The days of Chanukah are especially auspicious for Torah learning. This is unlike the custom today in which people use the days of Chanukah for games and other mundane entertainment.
It is customary for young adult paupers to collect charity money during Chanukah. Accordingly, one is to increase in giving charity during Chanukah. Giving charity during this time is a Segulah for rectifying various spiritual blemishes.
It is a Jewish custom, which is Torah, to distribute Chanukah Gelt to children. This was also the custom of the Chabad Rebbeim. One is to distribute even to his married children. The purpose of this custom is to motivate the child to learn Torah. Accordingly, one is to explain to the child upon receiving the money that it is being given so they increase in learning Torah.
When to give: Parents are to give Chanukah Gelt to their children every day of Chanukah, with exception to Shabbos. On Friday or Sunday, one is to give a double portion on behalf of Shabbos. One is not to give Chanukah Gelt on Shabbos, even in the form of non-Muktzah items. On the 4th or 5th night they should give a double or triple portion.
Distributing to students: A Rebbe is to give Chanukah Gelt to his students.
Distributing to spouse: Spouses are to request Chanukah Gelt from each other; the wife is to request from the husband and the husband from the wife.
May one play Dreidel for gambling purposes?
- Example: May one play Dreidel for winning money, chocolate coins etc.
Some write that it is permitted on Chanukah to play Dreidel for winning purposes, as on Chanukah people forgive items to each other just like by family. However, one is certainly to avoid playing with large sums of money or valuable items.
The Chassidic masters spoke ardently against playing cards, saying that it contains much impurity.
The last day of Chanukah:
The eighth day of Chanukah is called Zos Chanukah. On this day, there shines a great amount of G-dly light which is able to refine the greatest depths of evil. One is to increase in Torah learning on this day. On this day one can complete all matters of Chanukah which were not yet accomplished on the previous days.
The Rebbe’s Mivtzaim:
- One should endeavor that a Menorah is lit in each and every Jewish home.
- Boys of all ages should light their own menorah.
- One should gather children together and explain to them the miracle of Chanukah.
- One is to arrange that each Jewish boy and girl receives Chanukah gelt, and that they in turn also give to their friends.
- One is to increase in learning of Torah during the holiday
 Rambam Chanukah 3:3 “The days of Chanukah are days of joy and praise”; Megillas Taanis [and Megillas Antiochus] “it was established for festivities and joy like all the festivals written in the Torah”; Rashal 85, Bava Kama 7:37; Seder Hayom Chanukah “These are days of Sasson and Simcha”; See Likkutei Sichos 10 p. 142 [printed in Shulchan Menachem 3 p. 282-287]
 Rebbe in Shaareiy Halacha Uminhag 2:282
 Rashal 85
 P”M 670 A”A Hakdama
 Shlah Hakadosh Chanukah
 Shlah Chanukah; Biur Halacha 670:2 “Venohagin”
 M”A 670; Hashlama of Rav Nechmia of Dubravna end of 670
 Kitzur SHU”A 139:1; P”M 670 A”A Hakdama; Sefer Haminhagim P. 161 “Some are accustomed to increase…”; See Likkutei Sichos 5 p. 346; Igros Kodesh 23:301 [printed in Shulchan Menachem 3:262]
 Kitzur SHU”A 139:1
 Toras Menachem 5748 2:65; Likkutei Sichos 20 p. 452; Rebbe in Shaar Halacha Uminhag 2:283; Shulchan Menachem 3 p. 288-289; Sefer Haminhagim P. 161
 Toras Menachem ibid; See Likkutei Levi Yitzchak p. 358
 Toras Menachem ibid; As the Greeks nullified our Torah learning, and the idea of giving children money is connected with motivating them to learn Torah. [See Rambam Pirush Hamishnayos Sanhedrin Perek Chelek]
 Toras Menachem ibid
 Now, although the [Previous] Rebbe would distribute coins for “Chanukah gelt” (gifts of pocket money) on only the fourth or fifth night of Chanukah, in order so the children rejoice over the new receiving of the gift, nevertheless today with the great darkness of exile one is to give daily. [Rebbe ibid]
 Toras Menachem ibid, due to a decree
 This is in light of the custom of our Rebbeim to give Chanukah Gelt on the 4th or 5th night. Now, since today we give every day, therefore on the 4th or 5th night a double or triple portion should be given to commemorate this. [Rebbe ibid]
 Igros Kodesh 21:195
 Hisvadyus 5747 2 p. 132
 Bnei Yissachar Kislev 2:25; Minhagei Chasam Sofer that so was his custom; See Piskeiy Teshuvos 670:4
 The meaning behind the inscription of the Nun Gimel Heiy Shin, is to teach one that even when one is in the midst of mundane activity, such as playing a game, he is not to forget G-d. The playing of Dreidel also contains mystical meanings behind it, as explained in Bnei Yissachar [Kislev 2:25]. There he explains that it represents the fall of the 4 evil empires who placed the Jewish people into exile. There he mentions that the original custom was to use wood Dreidels, due to mystical reasons.
 Piskeiy Teshuvos 670 footnote 25 in name of Rebbe of Klozinberg
 See Choshen Mishpat 34:16
 Biur Halacha 670: “Venohagin”; Kedushas Levi Parshas Mikeitz; Bnei Yissachar
 Playing cards is a grave sin, as each card contains an unmentionable degree of impurity. [Kedusha Levi ibid]
 Sefer Haminhagim P. 161 [English]
The reason: This term follows the words “Zos Chanukas Hamizbeiach” which is read from the Torah on the 8th day of Chanukah. See Shaar Hamoadim Chanukah for a lengthy Sicha regarding why only the last day of Chanukah is called Zos Chanukah, as on Chanukah the main aspect is the Mikbael:Bepoel, as rules Beis Hilel, and hence only the last day in actuality has all eight lights lit.
 Shaar Hamoadim Chanukah 71
 Based on Shaar Hamoadim Chanukah 70
 Shaar Hamoadim Chanukah 72
 Shevach Hamoadim p.98