The Classic Reason
The common reason given for playing the game of dreidel on Chanukah is that the simple little top was used during the Chanukah era to preserve Judaism. When the Syrian-Greeks ruled over the Holy Land, they outlawed many Jewish practices, such as circumcision, Shabbat observance and Torah learning. With great self-sacrifice, the Jewish children would hide in caves to learn Torah. When they would see a Greek patrol approaching, they would quickly hide their scrolls and take out spinning tops, pretending to have simply been playing a game.
Despite the ubiquity of this reason, many mystics have ascribed much deeper symbolism to the game of dreidel. In fact, many of them don’t even mention the classic reason for dreidel. But to understand the deeper meaning of the dreidel, we first have to describe how a dreidel looks.
The Letters on the Dreidel
The dreidel is essentially a type of top with a Hebrew letter on each of its four sides. The four letters are nun (נ), gimel (ג), hei (ה), and shin (ש), which are commonly understood to be an acronym for the phrase נֵס גָדוֹל הָיָה שָׁם, “A great miracle occurred there.”
The mystics also ascribe deeper meaning to other aspects of the dreidel, including the position of the handle and the material the dreidel is made of.
Rabbi Yehuda Loew, known as the Maharal of Prague (1525–1609), explains that a person has four spiritual elements: the body (גוף–guf ), soul (נפש–nefesh), intellect (שכל–seichel ), and one that “includes and encompasses them all” (הכל–all).
He further explains that the Jewish exiles can be divided into four kingdoms that subjected and exiled the Jewish people: Babylon, Persia, Greece and Rome. Each of these kingdoms attacked the Jewish people in a uniquely different way, but, ultimately, the Jewish people were victorious.
The Babylonian Empire attacked the Jewish soul (nefesh), for they were the first to destroy the Temple and stop the daily offerings, which are connected to the soul, as the verse states, “And if a ‘soul’ brings an offering ...” The Persian Empire attacked the Jewish body (guf); as related in the Purim story, Haman tried to kill the entire Jewish nation. The Greek Empire, which produced some of the world's greatest philosophers, attempted to demonstrate the incompatibility of Torah with the intellect (seichel).
The last exile by the Romans, who destroyed the Second Temple, utilized all the above, attacking the Jewish body, soul and intellect, in an attempt to delegitimize the Torah and Judaism (the Hebrew word for "all" is hakol).
Thus, Rabbi Tzvi Elimelech Shapira (1783–1841), in his work B'nei Yissaschar, explains that this is the inner meaning of the dreidel. The gimmel of the dreidel stands for the Jewish body, guf (Persia); nun stands for the Jewish soul, nefesh (Babylon); shin stands for the Jewish intellect, seichel (Greece); hei stands for all the above, hakol (Rome).
Each kingdom/exile is depicted on a different side of the dreidel, representing our enemies’ surrounding us from all sides. Negativity is always represented by disunity. We spin the dreidel on one central point, representing the central unity of the Jewish people. This unity will eventually be realized by all nations of the world, as the verse says, “For then will I turn to the peoples a pure language, that they may all call upon the name of the L‑rd, to serve Him with one consent.”
Rabbi Tzvi Elimelech Shapira adds another point. If you add up the numerical value of the letters of the dreidel, you get 358 (nun  + gimmel  + hei  + shin  = 358).
This is the same numerical value of the word נחש, nachash, meaning serpent (nun  + chet  + shin ), referring to the snake that seduced Eve to sin in the Garden of Eden. It is also the same value as משיח, Messiah (mem  + shin  + yud  + chet  = 358).
In short, the dreidel then represents the idea that the “serpent,” which the sages explain corresponds to the evil inclination, the forces of negativity, and exile throughout the generations, will finally be transformed and vanquished with the coming of the Moshiach.
At some point, Jews living in the Land of Israel decided to change the last letter on the dreidel from a ש, which denotes a great miracle happened “there” (שָׁם), to a פ denoting a great miracle happened “here” (פֹּה). Based on this, the letters on the dreidel would be nun, gimel, hei, and pei, נגהפ , and their numerical sum would come to 138.
Some point out that this numerical value still hints to the final redemption, for 138 is the value of the word tzemach (צֶמַח), the name of the Moshiach appearing in the Bible, “Tzemach is his name ...” It is also the numerical value of the name Menachem (מְנַחֵם), which the sages of the Talmud say is the name connected to Moshiach.
A Wooden Dreidel
Dreidels are made of many materials, including metal, wood and plastic. In fact, Rabbi Moses Sofer, known as the Chatam Sofer (1762–1839), is known to have dedicated at least one night of Chanukah to play with his silver dreidel with his children. Nevertheless, some give special significance to wooden dreidels.
In the Haftorah of the Torah portion of Vayigash, which is read during Chanukah, the Prophet Ezekiel wrote about the final redemption on two wooden sticks:
"And you, son of man, take for yourself one stick and write upon it, 'For Judah and for the children of Israel his companions'; and take one stick and write upon it, 'For Joseph, the stick of Ephraim and all the house of Israel, his companions.'”
Indeed, it is specifically in the Torah portion of Vayigash that we find that Jacob, before going down to Egypt to meet his son Joseph, sent his son Judah ahead of him to Goshen: “He sent Judah ahead of him to Joseph, to direct him to Goshen (גּשְׁנָה) ...”—which makes up the four letters of the dreidel. This is not a coincidence, for it is specifically this verse which holds the secret to the Jewish survival throughout the long and bitter exile. As the Midrash explains, the reason Yaakov sent Judah ahead of the family was in order for him to set up a center for learning and spirituality before the whole family would arrive in Egypt.
Top or Bottom? Chanukah vs. Purim
On Chanukah, we spin a dreidel from the top. On Purim, we swing a gragger from the bottom. This represents the difference between the two miracles.
On Purim, the miracle came about from “below.” In the Purim story, the Jews fasted and prayed, while the miracle itself seemed to be hidden within events that unfolded within nature. On Chanukah, we don’t really find that the Jews necessarily were “worthy.” It was out of G‑d’s great mercy that He intervened from above with openly revealed miracles. Thus, on Purim, we swing the gragger from below and on Chanukah we spin the dreidel from above.
The game of dreidel teaches us that even when we are playing, we imbue the game with meaning, remembering our heritage and the miraculous salvations that G‑d performed for us in the past. We also express our longing for the final redemption with the coming of the Moshiach, may it be speedily in our times!