A friend recently asked me if I had any sources for the custom of playing with a dreidel on Chanuka and what it means. I responded:
See here, from R' Gavriel Zinner:The Bnei Yissaschar has some famous pieces on dreidel, one is that the dreidel is spinned from the top while a gragger is spun from below, symbolizing that on Chanukah the yeshua came through hisarusa d'l'eilah and Purim was a hisarusa d'l'sata. Also he connects the letters to the word "גשנה" in Breishis 46:28. I think he also points out that the letters are, b'gematria, "moshiach".While the custom to play with a dreidel on Chanukah appears to have been well established beforehand, I don't know of any written sources earlier than the 19th century.The Bnei Yissaschar doesn't mention the story of children playing dreidel to hide that they were learning Torah. This story is also not mentioned in Taamei Minhagim or Sefer Hatodaah (both of whom would almost certainly have mentioned it if they had heard of it and thought it was true). The earliest source I have found for this story is a sefer published in 1918 by a Rev. Hirshovitz in Pittsburg called אוצר כל מנהגי ישרון. (R' Zinner quotes it in his first footnote.) You can see it here:He says it in the name of some other sources but I have not been able to identify them reliably.As far as I can tell, this story began sometime in the second half of the 1800s. It is probably not a coincidence that at that same general time a number of writers (especially from the Mizrachi movement) were engaged in efforts to "romanticize" Jewish history, to give it more appeal to young people and reinforce nationalist sentiment. I suspect that this story grew out of that general tendency.
If anyone has any additional sources, please let me know.