The most famous question about the holiday of Chanukah was posed by Rabbi Yosef Karo (1488-1575, author of Shulchan Aruch, the code of Jewish Law) in his work called Beit Yosef. The Talmud in tractate Shabbat 21B teaches us the basis for the establishment of the holiday of Chanukah:

When the Greeks entered the Sanctuary they defiled all the oils (that would be used for the daly lighting of the Menorah in the Temple) that were in the Sanctuary. When the Hasmonean monarchy (the Maccabees) overcame them and emerged victorious over them, they searched and found only one cruse of oil that was placed with the seal of the High Priest, undisturbed by the Greeks. There was sufficient oil there to light the candelabrum for only one day (it was meant to burn throughout the night). A miracle occurred and they lit the candelabrum from it for eight days. The next year the Sages instituted those days and made them holidays with recitation of (the prayer of) Hallel and special thanksgiving in prayer and blessings (this refers to the prayer of Al HaNissim).

Now if we celebrate Chanukah to commemorate that miracle we need to ask ourselves over how many nights did that miracle take place? The answer should be seven because there was enough oil for one night. Why then are we celebrating for eight nights?

There are literally hundreds of answers offered to answer this question. Here are (don’t worry) a few of them (these are not Rabbi Karo’s answers).

Although they poured in the full measure for the first night and the Menorah burned throughout the night, they discovered the next morning that only an 1/8 of the oil was burned! Each subsequent night this miracle repeated itself. Thus the first night was also a miracle.

Another answer offered is that the Talmud tells us that the cruise of oil had the seal of the Kohen Gadol (the High Priest) on it. It was not the practice for the Kohen Gadol to put his seal on the oil used in the Beit HaMikdash. So why did this one have it? The Kohen Gadol brought a daily Mincha offering (a meal offering of flour and oil mixed together and offered on the altar) called the Minchat Chavitin (מנחת חביטין). It was brought from his own oil. We can therefore say that the cruise of oil with his seal was the oil he had set aside for his personal meal offering. Now, the amount of oil the Kohen Gadol needed for that offering was three lugin (a lug is a liquid measure recorded in the Torah). The amount needed to light the Menorah though was three and a half lugin. The oil they found was actually short the amount needed for the Menorah lighting. But that was the only pure oil available so that’s what they used. And it still lasted throughout the night! Thus the first night was a miracle.

The last answer is that the first night actually was not a miracle. We look at it that way because we take for granted that oil will burn. That’s it’s nature. The truth is that nature is also a miracle. Oil only burns because Hashem decreed upon it to do so just as He decreed upon a cruse with oil to burn for one night that it should burn for eight. As we celebrate the supernatural miracle of the oil the Sages wanted us not to forget the natural miracle of oil. Therefore the first night, the night that there was enough oil for, is the first night of celebrating the miracles of Chanukah.

Shabbat Shalom and Happy Chanukah!
Yitzchak