The custom of partaking of dairy foods on Chanukah in commemoration of Yehudit is sourced in the Rishonim quoted by the Rama (Chapter 670). The Ben Ish Chai (Parashat Vayeshev, Section 24) writes that since this enemy general was one of the Assyrian-Greek kings and he also wished to cause the nation to relinquish the faith we commemorate this miracle as well during Chanukah.
Though the original sefer is not connected explicitly to Chanukah or the Macqub'im, the story becomes connected to Chanukah when it shows up in medieval Jewish folklore and rabbinic discourse in both Sephardic and Ashkenazic communities. In all these versions, when General Holofernes besieges the Jewish capital, a beautiful, sharp-witted, bold widow named Yehudit convinces him that she will help deliver Jews to him, then gets him drunk until he passes out, takes his sword, and cuts off his head. Emboldened by the sight of their oppressor’s severed head, go on the offensive and vanquish their enemy.
When we consider this minhag in context of its full meaning. We can easily understand why oily foods are popular and contemporary Chanukah folklore celebrates the abundance of oil with which Hashem miraculously rewarded the faithful for their religious devotion.
Dairy food however is the medieval minhag which is reflected as the tool used to lure a person to sleep for the sake of committing righteous violence against him. In this way, the medieval versions of the Yehudit story recognize the echoes of Yael luring General Sisera to sleep and smashing a peg through his skull (Judges 4:18-21). Just as Yael’s tool for coaxing him to sleep was milk, in the medieval story Yehudit uses cheese to lure her enemy to sleep so she can kill him.
What we find in the Megillah of Yehudit is how it aligns Chanukah and its celebrations with Purim and its feast, using language taken directly from Megillat Esther to tell Yehudit’s story. In this telling, Chanukah, too, is a day of “sending portions to one another” (Esther 9:22). Like our Purim feasts, the Chanukah celebration should mimic the wicked buffoon King Ahasuerus’s feast, in which “the drinking was according to the law: none did compel” (Esther 1:8).
This medieval Chanukah is not just a festival of oil burning long once the messy war stuff is over; it is the kind of “feasting and joy and good day” (Esther 9:19) marked by celebrating violently slaughtering those who would have done us worse. This perhaps suggests that brutality and caprice are the ways of the world, and perhaps that villain and hero are hard to distinguish.
The translators error has caused many to believe that on Purim, “a person is obligated to become intoxicated to the point of not knowing the difference between cursed Haman and blessed Mordekhai” (Talmud Bavli, Megillah 7b).
(It should be noted that along side many Sephardic Poskim this practice was also condemned by the Lubavitcher Rebbe).
In the Megillat Yehudit Chanukah we engage in similar revelry: the text calls Yehudit a queen and describes her presiding over the feast with the same language used in the Megillah of Esther to describe Ahasuerus’s festive conduct: “Queen Yeudit had appointed to all the officers of [his] house, that they should do according to every man’s pleasure” (mimicking Esther 1:8).
So how did Sephardim learn to observe this minhag of consuming dairy? What is the real meaning and should we still observe?
For Sephardim I can only assume that the Ran was influenced by Ashkenazim as we know that Jews of Yemen did not consume dairy on Shavuot before the 14 century. This is added to a long list of other customs which are not belonging to Sephardim proper.
What we can see thus far is that for Chanukah, cheese functions like alcohol on Purim: meaningful in its brutally honest embrace of the violence of the world, in its recognition that oppressors have lured us to sleep in order to abuse us, and in its contrast to sober, controlled, ordinary behavior.
In a world without systemic justice, there exist our soporific wine and cheese, will we will fantasize about luring the oppressors to sleep so that we can destroy them?
Conclusion: May will elevate the Minhag and spirit of Chanukah and bring about true light and change to the world in which we live for the generations which are coming.