Having a cup of wine [i.e. Kos Shel Bracha] while Bentching:
There is a dispute recorded regarding the obligation of having a cup of wine, otherwise known as a Kos Shel Bracha, present while reciting Birchas Hamazon, and then having a blessing of Hagafen recited over it at the conclusion of the Bentching. The arguments extend between when it is required and if it is required at all.
A. The dispute:
First opinion-Obligation even upon individual: Some Poskim rule that it is an absolute [Rabbinical] obligation to recite Birchas Hamazon over a cup of wine, even if one is alone [i.e. ate by himself and is Bentching without a Zimun]. If there are two people eating together, then each one must have their own cup of wine when he Bentches. However, if there are three people eating together and making a Zimun, then only the Mizamein is required to have a cup of wine. According to this opinion, one is required to search for wine for Bentching, just as one is required to place effort to fulfill all other obligatory Mitzvos. If even after one’s search, he was unable to find any wine [or any other beverage defined as Chamer Medina] then if he expects to get a hold of wine later on, then he must delay eating his meal until he gets the wine, even if this means there will have to skip one meal. [Meaning, that if he desires to eat bread for lunch and does not have wine available but expects to get wine by dinnertime, then he should not eat bread for lunch. If, however, he does not expect to get wine until the next day by breakfast time, then he may have bread for lunch, but may not have bread for dinner.]
The second opinion-Only obligatory when there is a Zimun: Some Poskim rule that it is only an obligation to recite Birchas Hamazon over a cup of wine if one is Bentching with a Zimun [whether of three or ten men]. [However, if one is Bentching alone, or without a Zimun, then he is not required to have a cup of wine.]
The third opinion- Mitzvah Min Hamuvchar by Zimun: Some Poskim rule that there is never an obligation to recite Birchas Hamazon over a cup of wine, even if one is Bentching with a Zimun. This applies whether by a Zimun of three or even a Zimun of ten. Nonetheless, when there is a Zimun, it is a Mitzvah Min Hamuvchar to recite Birchas Hamazon over a cup of wine. However, this only applies if one has wine available, although one is not obligated to search for wine as one is required to do after obligatory Mitzvos. The above Mitzvah Min Hamuvchar only applies by a Zimun, however, when one is Bentching by himself [i.e. without a Zimun] then one does not need to Bentch over a cup of wine at all even for the sake of a Mitzvah Min Hamuvchar, even if he has wine available. [In other words, according to this opinion, there is no Mitzvah Min Hamuvchar to Bentch over a cup of wine unless there is a Zimun taking place.]
Opinion of Kabalah-Not to have unless Zimun: According to the teachings of Kabbalah, one is not to recite Birchas Hamazon over a cup of wine unless there is a Zimun present. [However, when a Zimun is present, then a Kos Shel Bracha is required.]
B. The final ruling:
Coming up in Part 2!
 See Admur 182:1; 296:13; 299:6; 477:8-9; Michaber 182:1; Tur 182; Piskeiy Teshuvos 182:1
 1st opinion in Admur ibid and 296:13 and 477:8 [and implication of Admur 46:1]; 1st opinion in Michaber ibid; Tosafus Pesachim 105b in name of Rashbam and Reb Yechiel of Parish; Rabbeinu Yonah Brachos 50b; Rosh Pesachim 10:14 and Brachos 8:2; Hagahos Maimanis Brachos Samech in name of Maharam of Rothenberg; Mahrahm 507; Tashbeitz 303; Kol Bo 25
 Admur 296:13
 Admur ibid; Michaber ibid; Kol Bo 25
 Admur ibid; Levush 182:1
The reason: As just as he fulfilled their obligation for the actual Birchas Hamazon, so too he fulfills his obligation for the cup of wine. [Admur ibid]
 Admur ibid; Michaber ibid; Ramban Milchamos Brachos 8; Rabbeinu Yerucham 16:7; Ran Pesachim ibid
 See Admur 182:2-3
 Admur ibid; Michaber ibid; Tur 182
Other opinions: Some Poskim rule that there is no source prior to the Tur for this ruling which prohibits eating bread if you don’t have a cup of wine and expect to receive wine later on, and therefore they conclude that one who is lenient has not lost out. [M”A 182:1] Practically, one may regardless be lenient in this matter being that there Poskim who rule that Bentching require a cup of wine at all. [Elya Raba 182:2] See Kaf Hachaim 182:3
 2nd opinion in Admur ibid; 2nd opinion in Michaber ibid; Hagahos Maimanis Brachos Samech in name of Riy and Rav Elchanon; Midrash Hanelam Rus; Zohar Chadash 47a
 3rd opinion in Admur ibid and 2nd opinion in 296:13 and 299:6 and 477:8; 3rd opinion in Michaber ibid; Rambam Brachos 7:15; Rif Pesachim 105b; Rashba Brachos 52a and Shut 1:342; Ran Pesachim ibid; Raavad Brachos 8
 Admur ibid; Rama ibid; Raavad ibid; Ran ibid; Ramban ibid; See Shaar Hamitzvos Eikev p. 106 “If there is a Zimun of three, and there is wine, then one should Bentch over wine”
 Admur ibid; Lechem Chamudos Brachos 8:5; Malbushei Yom Tov 182:2; Kitzur SHU”A 45:1; Ben Ish Chaiy Shelach 16; Kaf Hachaim 182:4
Contradiction in Admur: See Admur 299:8 in parentheses where he writes that according to all there is a Mitzvah Min Hamuvchar to Bentch over a cup of wine [even Beyachid]. See also Admur 296:13 who does not differentiate between a Yachid or Zimun when mentioning the Mitzvah Min Hamuvchar to Bentch over wine according to the lenient opinion.
Other opinions: Some Poskim rule that according to this opinion it is a Mitzvah Min Hamuvchar to Bentch over a cup of wine even Beyachid. [Possible understanding of Rama 182:1; Levush 182; Poskim in Kaf Hachaim 182:4]
 Admur ibid in parentheses “This custom [of not having a Kos Shel Bracha when Bentching alone] is correct according to Kabalah.”; Beir Heiytiv 182:1 and 4; Yad Aaron 182; Or Tzadikim 23:33 and in Kuntrus Derech Seuda “according to Kabalah, it is forbidden to take a Kos Shel Bracha for Birchas Hamazon if a Zimun is not present.”; Shaar Hamitzvos Eikev p. 106 “If one is alone, he should not Bentch over a cup”; Zohar Parshas Teruma 2:157 “A Kos Shel Bracha is only with three”; 168; Parshas Pinchas 3:246 “Three need a cup”; 274; Kaf Hachaim 182:1 and 15; See also Rama 182:2
 See Shaar Hamitzvos and Zohar ibid; See Kaf Hachaim 182:1 that so is the final ruling, to follow Kabalah that Kos Shel Bracha Beyachid is forbidden, as whenever there is no clear Halachic ruling, then we follow the Mekubalim
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