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Thought for the Day: Havdala for a Jew Who Didn't Keep Shabbos

(Based on shiur by R' Fuerst, shlita: Interesting Teshuvos from HaRav Shteinman ZT”L.)
Here's the setup: an irreligious Jew (we'll call him Koby) in Israel went to his neighbor, a Torah observant Jew (we'll call him Yaakov), on Saturday night and asked him to make havdala for him. Why? He was having an issue with his eyesight, and had heard that putting the wine from havdala into one's eyes is a סגולה (by which he meant supernatural cure) to heal eyesight. Koby wanted Yaakov to make havdala for him, so he could put some of the wine into his eyes.

This is wrong on so many levels. First, of course, is treating Havdala as some sort of voodoo. Second: why couldn't Koby just make Havdalafor himself? Even if he were a recent immigrant (which he was not), there is always an ArtScroll siddur around. Etc, etc, etc...

Ok; let's cut to the chase: Is a Jew who did not keep Shabbos obligated in Havdala? As it turns out (you may need to sit down for this shocking bit of news.... ok, comfy?): it is a מחלוקת הפוסקים/controversial among those who decide normative Jewish law. It is easy to understand the opinion of those who contend that a Jew who did not keep Shabbos is still obligated in Havdala. After all, the performance of one mitzvah is not normally dependent on the performance of another mitzvah. According to those who hold he is not obligated, however: why is Havdala different?

Havdala, by it's nature (and, in fact, the definition of the word) is to separate/distinguish between the sanctify of Shabbos and the ordinariness of the week. Just as we bring in Shabbos with Kiddush, we usher it out with Havdala. Perhaps one is only obligated in Havdala if he kept Shabbos just as one is only obligated in the mitzvah of Birkas HaMazon if he actually ate. One might argue that eating is optional, whereas Shabbos is an obligation, so the cases are not comparable. However, we do have one case where eating is obligatory: matzah on Pesach. Still one might argue that the bentching is going on the food that is still in one's stomach, and not on the fact that he ate.

The sense of the poskim is that Koby is, in fact, obligated in Havdala. Does that mean that Yaakov should make Havdala for Koby so that Koby can put magic wine in his eyes? R' Shteinman advised that Yaakov should demur and tell Koby that the סגולה of Havdala wine is for those who keep Shabbos. In fact, since it is such a chutzpah, the סגולה may have the opposite effect and be damaging to Koby's eyesight. R' Fuerst feels that it might be different in America, where this could be used as an opportunity to bring Koby closer to Torah. (I am not sure why R' Fuerst makes this distinction between America and Israel.)

Besides this (it seems to me) rare request, the question actually has much broader implications. Namely: since you are not allowed to do malacha after Shabbos until saying Havdala, what happens if you get a non-religious Jewish taxi driver after Shabbos? If he is obligated in Havdala, then you are not allowed to have him drive for you until after he recites at least a minimal Havdala. You'll have to listen to the shiur to find out more.

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