Sefarim Debate which of the 613 mitzvos is the ‘Hardest’ to fulfill.
We add one more Mitzvah to this, and learn Pesach lessons along the way.
Last year, as I was leaving shul to head to my Pesach seder, I was stopped by a young bachur. The question he asked, and the answers I ultimately discovered, are worthy to share and may have a positive impact on the reader’s Pesach and seder. Before sharing his difficulty, let’s first put ourselves into the mindset behind his vital enquiry.
The sifrei machshava frequently share that it is often the very issue, mitzvah, or nisayon, that challenges us most where we may discover the greatest potential growth, and from which one may discern their unique tafkid in this life. Correspondingly, there are certain obligations that are a challenge for all klal yisroel, and from which the Torah testifies to their same power in unleashing our kedusha and dveykus should we accomplish them.
On this note, some of our gedolim have wondered the following: What is the most challenging mitzvah -from all of the taryag mitzvos and seven mitzvos m’derabanan, as well as the myriad Rabbinic legal protections?
While this is certainly a subjective question, over the years, many candidates have been offered by gedolim.
The Ksav Sofer had his own proposed candidate (Shu’t Ksav Sofer, Orach Chaim, siman 57), stating: “…and in truth the mitzvah of tochacha (rebuke) is more difficult to accomplish properly more than any mitzvah in the Torah”. And, indeed, if done properly we could remove all sin!
The Gra offers another mitzvah as the most challenging to observe properly: the obligation to be in a state of simchah on the yomim tovim (Devarim 16:16; Divrei Shalom, p. 36; shu”t Mishneh Halachos 7:75). While the Rambam (Peirush Mishnayos, avos, 2:1) posits that this mitzvah is one that many assume is easy (mitzvah kalla), he, perhaps, was only speaking of our mistaken presumptions.
On this theme of simchas yom tov, the Brisker Rav is quoted as saying that the yom tov of sukkos is therefore the hardest, as the simcha must last every second! Rav Reuvein Benges is quoted as saying, “Certain types of minor chametz on Pesach may only be a violation of a derabanan, whereas just a trace of sadness may be a violation of a Torah law!” (Shu’t Teshuvos V’Hanhagos, 5:155). This helps explain why we are told in ki savo that to avoid the tochachos we need to serve Hashem with Joy, as within our greatest challenge is also our greatest refuge.
Indeed, the challenge in keeping any of the mitzvos that rely on our emotions is echoed by Rav Baruch Eptsien in his Tosfess Beracha: “Why in Hillel’s response to the convert regarding the verse, “Love your fellow as yourself,” [does he add] “What is hateful to you, do not do to your friend.”?…This is because the emotion of love is relegated to the heart, making it impossible to require such matters. So, it is taught as refraining from harmful actions against another, for this too can be learnt from the verse…“
Let’s simplify this question, and ask instead: What is the most challenging mitzvah to be mikayem over Pesach?
Rav Shlomo Brevda quotes in the name of the Gra that just by the seder alone there are sixty-four mitzvos to be fulfilled (Leil Shemurim, p. 46, 47)! This is not to mention the unremitting obligation to avoid eating, benefitting or owning chometz, etc.
If you ask a yeshivah bachur this question, they may respond “Fulfilling the proper shiurim on leil Pesach”. A father may answer “V’higadeta l’vincha, to have a true dialogue with one’s children about our geula is most difficult to satisfy properly”.
Now I can share the shailah I was asked last year, upon which I immediately recognized realized that this may be the most challenging mitzvah of the night, if not the year. Rav Shternbuch makes the same case, writing how “One of the gedolei hador once shared with me that this is the hardest mitzvah, and how at the end of each seder he was concerned if he fulfilled it, even at bdieved level”. (Hagadas Moadim Uzmanim, p. 86).
To what mitzvah do I refer? It comes from a mishneh (Pesachim 116b), and we say it by the seder:
“In every generation, each person must see himself as if they are exiting mitzraim”
Is there a mitzvah more challenging?!
When the bochur asked me last year how to best fulfill this mitvah in accordance with all views, I was unable to answer right away. After much thought and research, I would later share with him the following.
Rav Yechezkal Landau underscores the seeming incongruity of this mitzvah. It is one thing to feel this way when the beis hamikdosh stood, he writes, but today – with all of our suffering – how is this emotional state even possible?! He even points to the incompatibility of such an emotion when slavery still exited (in his day) around the world! (Derushei HaTzleach, 1967 edition p. 53a bottom of first column, 51b bottom of first column, and 52a first column).
Countless other questions abound regarding this mitzvah -both in lomdus and hashkafa. Due to these, the sefarim state something unbelievable (see in particular, Emek Beracha, pesach, 3; see also Netziv to shmos 34 and devarim 16 and Sefas Emes, pesach, ’58, inter alia.).
“The hallel and thanks we offer on Pesach is unique, and different than that of any other yom tov. On, say Chanukah, we are recalling and thanking Hashem for what He did for us long ago. However, on Pesach, we are also referring to the here-and-now, our own personal geulah…” This is why the Rambam adds one crucial word to this mitzvah: “In every generation, each person must see himself as if they are exiting mitzraim ‘atah/now”! (Emek Beracha, ibid.).
This too is why Pesach carries a seasonal obligation -from which much of our calendar is derived. Pesach, the Torah says, must be in the aviv/spring. The word aviv comes from avah, meaning hopes/yearnings (this bis where the word taavah comes from, see, e.g. bereishis, 24:5; See Rav Hirsch Chumash, shmos, 9:30).
Each spring we see the dead trees converted to life, the cold turn to warmth, and the darkness transformed to light. This is Pesach!
By the time we reach the end of magid, our goal is to take the lessons from the story of the hagadah and to then transfer our own struggles and challenges onto that prism. By doing so, one will find themselves calmed with the relief in the knowledge that just as Hashem did for us in the past, so can he do for us in the future. Both individually in our personal lives, and for us as a nation.
This is a most amazing chiddush, and one that make this mitzvah, while still challenging, plausible. More, this mitzvah becomes aspirational for the entire year. Pesach in general, and sipur yetzias mitzraim in particular, is an emunah reset.
So yes, this is still a most difficult mitzvah, yet one with a clear path of accomplishment. And, as we began, the nisayon in its kiyum alludes to the fact that from it one can gain stupendously in their dveykus to Hashem, as well as solace and hope in their own lives.
May Hashem indeed bring each of us a persanol and communal geulah!
Chag Kosher V’Sameach!
Rabbi Moshe Taub is the rabbi of Young Israel of Holliswood and rabbinic editor and weekly contributor for Ami Magazine. He is the author of Jews in the World (Mosaica Press) and writes on Jewish law, history, and thought at ShulChronicles.com.

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