1) Hamantaschen are eaten in remembrance of the great hidden miracle of Purim. A hamantasch is essentially a cookie whose filling is hidden inside the dough, just as the miracle of Purim was hidden under the guise of nature. Until the destruction of the First Beis HaMikdosh, which occurred shortly before the time of Purim, the Jews regularly saw open, supernatural miracles. However, with the destruction began a period that lasts until today, where Hashem operates in a behind-the scenes fashion, and His hand is not so apparent in daily events.
The Purim story was the first time the Jews realized that the absence of overt miracles did not mean that Hashem had abandoned them. Instead, they realized that Hashem had a new modus operandi, as they understood how the Purim miracle was concealed and hidden within nature. Although as an observer at the time might misinterpret the events as normal and natural political happenings, every step of the Purim story was directed by the hand of Hashem. (Sefer Menuchah V’Kedushah 2:20)
2) One of the main themes of Purim is that of “v’nahafoch hu”, the turnabout. The story represents not only salvation from our enemies, but a complete reversal and interchanging of situations for the parties involved. The Jews switched from being completely dominated by their enemies to completely dominating them. There are many avenues through which Hashem could have caused His plan to come about. On Purim, Hashem used Haman the very person who desired to destroy Hashem’s people, to actually bring about their salvation.
Haman’s decree to annihilate the Jews caused a massive teshuvah movement and recommitment to the Torah, culminating in the hanging of Haman on the same gallows he had built to execute Mordechai. We eat hamantaschen on Purim, a sweet cookie named after the bitter Haman, to symbolize the v’nahafoch hu of how Haman and his evil actions turned into the source of sweetness and nourishment for Jewish survival. (Rabbi David Aaron, Endless Light pg. 81-82)
3) Nowadays, hamantaschen are filled with all types of jellies, jams, and even chocolate. However, originally, they were filled with either sesame or poppy seeds, designed as another method of fulfilling the minhag of eating seeds on Purim. Therefore, hamantaschen are effectively pocket pastries filled with poppy seeds. In Yiddish, poppy seeds are called “mohn”, and pockets are called “taschen”, revealing the source of the name mohn-taschen. Beginning with the minhag of eating seeds, this pastry became a Purim mainstay because of the similarity of the word mohn (מהן) to Haman (המן), both in pronunciation and in spelling. For this reason, the name mohn-taschen eventually evolved into hamantaschen. (Sefer Matamim, Purim 2)
4) The word tash in Hebrew means to “weaken”. On Purim, we specifically eat the pastry hamantaschen because it means “Haman became weakened”. This commemorates Hashem saving us by weakening Haman during the time of Purim, and in addition express the wish that Hashem should always save us by weaking the Haman’s of every generation. (Otzar Kol Minhagei Yeshurun, 50:11, pg. 126)
5) On Purim, we eat hamantaschen, a food that carries the name of Haman, because as eating destroys the food being eaten, we symbolically fulfill the mitzvah of destroying Amalek by eating Haman. (Sefer HaMoadim, vol. 6, pg. 153; Rav Yaakov Kaminetzky, BeMechitzas Rabbeinu HaGaon Rabbi Yaakov Kaminetzky, pg. 142)
6) Haman offered ten thousand kikar, talents, of silver to Achashveirosh for permission to exterminate the Jews. We eat hamantaschen specifically filled with poppy seeds because the countless number of poppy seeds in the “Haman-taschen” (“Haman-pockets”) commemorates the ten thousand kikar of silver Haman had in his pocket to offer to Achashveirosh. (Sefer HaMoadim, vol. 6, pg. 154)
7) The Alshich explains that at first, the Jews did not believe that they were going to be completely wiped out. In an effort to convince them of the seriousness of the situation, Mordechai sent numerous letters to the Jews describing the true brutal natures of Haman and Achashveirosh. However, because Mordechai feared the king might intercept these messages that painted him in unfavorable light, Mordechai hid them in pastries, which he then sent to the Jews. These pastries saved the Jews, because when they found Mordechai’s letters hidden within the dough, they became convinced of the direness of the situation and were stirred to repentance. On Purim, we eat hamantaschen, a pastry that contains hidden filling, to commemorate how the hidden filling of Mordechai’s pastries brought about our salvation. (Sefer Menuchah V’Kedusha 2:20)
Why Do Hamantaschen Have Three Sides or Corners?
1) The three-sided shape represents the three avos, Avraham, Yitzchak, and Yaakov, whose merit helped save the Jews on Purim, by causing Haman to become “tash”, weakened. (Sefer Matamim, Purim 2)
2) Traditionally it is thought that the three corners of the hamantaschen are reminiscent of the three-cornered hats worn by Haman and those in Persian court. These hats may have resembled the tricornered hats worn by Napolean or George Washington. Hamantaschen were fashioned and baked into the shape of Haman’s hat to further the symbolism commemorating his downfall. (Sefer HaMoadim, vol. 6, pg. 154).
3) I would like to add one more idea, behind the three-sided shape of the hamantaschen which someone sent me:
Rav Efraim Shapiro shared that the Maharal teaches that you learn the מהות, the essence of something, by looking at its central features. The middle letter of the whole Torah is the letter “vav” in the word גחון in Parshas Shemini.
The letter “vav” is unique because it can be written in three ways:
וו = 12, representing the 12 shevatim – ישראל
22 = ויו, representing the aleph beis representing, תורה - אורייתא
ואו = 13, whose numerical value is 13, which is the same as the value of אחד, representing Hashem Yisborach - קודשא בריך הוא .
ישראל , אורייתא, קודשא בריך הוא חד הוא
The Shevilei Pinchas writes that the Megillah begins with a “vav” (ויהי), ends with a “vav” (לכל זרעו), and in the middle it contains a “vav” (ותען אסתר ותאמר).
The goal of the Megillah is to combine ישראל, אורייתא, קודשא בריך הוא.
Furthermore, the Torah teaches us וחי בהם.
The gematria of חי is 18 or 3x6. One has חיות, life, when one combines the 3 vavim.
But what is בהם? The gematria of בהם is 47. If you go back to the values of the vavim, 12 + 22 + 13 = 47.
Moreover, when Haman asked Mordechai about what he was learning he replied קמיצת העומר. When Haman heard this, he replied, “if that’s the case, then you are going to win”. קמיצת העומר is performed by bending the 3 middle fingers representing the 3 vavim.
Finally, a hamantaschen is constructed with 3 vavim. But what makes it unique? The מלוי - the filling.
וחי בהם
We need to derive חיות serving Hashem with the מלוי - combining all 3. Fill oneself with connection to Hashem with tefillah, tehillim, with limud haTorah, with enthusiasm for mitzvos and fill oneself with ahavas habriyos.
