1- So the story is about Shimon of Timna who missed coming to the ‘Drashah’ of Reb Yehuda on the night on Yom Tov.
We mentioned that this is perhaps the ‘minhag’ to go on ‘tahalucho’ to say/hear a dvar Torah on the second night of Yom Tov.
Shimon replied that his town was besieged by a garrison – “בלשת” – of soldiers who threatened to loot all Jewish monetary possessions. In order to appease them the Jews prepared a meal by slaughtering a calf for the soldiers to feast on. Being occupied with this unfortunate situation, concluded Shimon, did not allow him to attend the ‘Drashah’ of Reb Yehuda.
Reb Yehuda tells Shimon “I wonder if your gain (of averting the looting of property) is negated by the loss of transgressing the prohibition of cooking for a goy on Yom Tov.”
Or as Binyomin Rosenberg phrased it: The Juice is not worth the squeeze.
From Reb Yehuda criticism of the actions of Shimon (slaughtering the calf and thereby saving the town from being completely plundered) it seems that if he were asked, his ruling would be to allow themselves to be robbed and lose everything in order not to transgress the prohibition of cooking for a goy on Yom Tov!
2- We mentioned the general rule of how much a person is obligated to spend on Mitzvos.
The consensus is, as per the Ramo, that for a Mitzvas Ese (or any passing Mitzvah) one needs to spend up to one fifth of his net worth. So if someone is stuck on an island and only one Esrog is available but at an exorbitant price, he is obligated to purchase it if the cost is up to a fifth of all he is worth.
To put this in perspective: A homeowner living in in Crown Heights – BH the value of the property is easily $1 million. Say with a mortgage of $600,000 leaving equity of $400,000….one would need to spend up to $80,000 for the אתרוג…
On the other hand, in order not to transgress a lo sa’se one must spend his entire net worth!
For example, if one is forced to eat crabs and the only way out is to bribe his captors, he is required to give them all he owns not to eat the non-kosher food.
3- Now let us understand the story of Reb Yehuda and Shimon.
The transgression of the prohibition of cooking for a goy on Yom Tov is an עשה. One is permitted to cook on Yom Tov but only for the purpose of eating and for a Jew only. לכם ולא לנכרי. But that is an עשה, and a maximum of a fifth is to be spent as above.
So why did Reb Yuhuda rebuke Shimon? The town acted accordingly in not allowing to lose everything they owned just to fulfill an עשה!
4- We discussed the logic of the above rule. עשה versus לא תעשה.
In general – which is more important? An עשה or לא תעשה? From the fact that עשה דוחה לא תעשה it seems that an עשה is greater.
The Alter Rebbe states it explicitly in the beginning of Igeres Hatshuva. [He explains there as to why תשובה for an עשה is easier that for a לא תעשה].
But in a certain aspect the opposite may be true. By not performing an עשה (like not eating Matzah) one does ‘nothing’. There is nothing ‘acitve‘ on his part by not eating Matzah. He just sits back and lets the night pass by.
Conversely, by transgressing a לא תעשה, one is actively performing a prohibited commandment. The חוצפה so to speak and the ‘rebelliousness’ – מרידה , is more evident in a לא תעשה than a מצוות עשה.
So perhaps this the reason one is required to spend everything on not transgressing a לא תעשה: One needs to avoid to ‘rebel’ at all costs!
5- In light of the above – we spoke about a case of transgressing a מצוות עשה, but with an act that is proactive – קום ועשה.
For example our case. Under normal circumstances the לכם ולא לנכרי is a passive עשה. ‘Cook (but) only for yourselves’.
But in our case, by cooking for a goy, one transgresses the עשה in an active way!
So therefore Reb Yehuda was correct in telling them that they acted incorrectly for they needed to spend everything to prevent transgressing this עשה.
We mentioned the משנת חכמים that tackles this issue. See here.
(ראה מ”ש בפת”ש סי’ קנז סק”ה מחלוקת הפוסקים אם החיוב בל”ת להוציא כל ממונו הוא דוקא בלאו שיש בו מעשה)
We related one of his quips as to why American Jews assimilated.
See the Pushkas for Yeshivas.
7- We concluded with a riddle as to where the Alter Rebbe writes (and it pertains to our Gemara):
ומילתא דפשיטא שאין לסמוך על התניא