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2. Rashi’s answer
3. Harav Kook’s answer: God-worship now and then
Altars now and then
"Neither shalt thou set thee up a pillar, which the Lord thy G-od hateth" (ch.16, v.22). We saw that our ancestors used pillars for the service of G-od: When Jacob had slept in Beit-El on his way to Lavan, he "took the stone that he had put under his head and set it up for a pillar, and poured oil on the top of it" (Genesis 28,18). On his return from Padan-Aram, Jacob comes back to Beit-El and again - "Jacob set up a pillar in the place where He spoke with him, a pillar of stone, and he poured out a drink- offering thereon, and poured oil thereon" (Genesis 35,14). In contrast to this, it is said at the beginning of our Portion -"Neither shalt thou set thee up a pillar, which the Lord thy G-od hateth" . The Torah was not satisfied with only determining that making a pillar is forbidden, but also added that it is hated by G-od!
Rashi’s answer
Rabbi Abraham Iben-Ezra explains that the prohibition mentioned here relates only to pillars being made for idolatrous worship, but a pillar being made for the sanctification of G-od was not banned. Rashi, however, claims that this prohibition relates to every pillar whatsoever, even in order to sacrifice on it to Heaven. Therefore he explains that although "it was pleased to Him in the days of our ancestors, now He hates it". Why? "because they (the Canaanites) made it an ordinance of an idolatrous character". Rashi also explains the difference between a pillar and an altar: a pillar is one stone made for sacrifice, and this is forbidden, while an "altar of stones and an altar of land He has commanded you to make".
Harav Kook’s answer: God-worship now and then
While Rashi brings a historical explanation of the "change" - as it were - in G-od’s attitude to the pillar, Harav Kook (Letters, No.746) provides us with a theoretical-conceptual one. Rambam describes the pillar as a monument around which people are gathered for worship. This way of worship - says Harav Kook - was pleased in the days of the ancestors, when there was not yet any difference between the nations, and Abraham called all the inhabitants of the globe to appeal to G-od. This was Abraham’s unique way, to teach all human-beings that there is a Master of this world. This "universal" approach suits the character of the pillar, which gathers everyone around it, without making any differentiation between one person and another.
In the days of the descendant, however, there is already a special nation, which has received a Torah, with a detailed Devine instructions about the Devine service. From this point on worship of G-od is done "in the house". A house has walls, which separate the inside from the outside. Only those who deserve being in the house are allowed to enter, and the level of their worship is much higher.
Jacob foresaw this and said: "And this stone, which I have set up for a pillar, shall be G-od’s house" (Genesis 28,22). That is to say, not a pillar, which everyone gathers around but a house made of surrounding walls, designed for the worship of only those worthy of it.
Our Sages of Blessed Memory (Tractate Pesahim p. 88) say: "What is the meaning of the verse ‘And many nations shall go and say: Let us go and climb the mountain of the G-od, the house of Jacob’s Lord’? - Not as Abraham, who called it a mountain and not as Isaac, who called it a field but as Jacob, who called it a house". A mountain is an elevated area that one may approach from any side one comes. That was Abraham’s way, of bringing everyone beneath the wings of Presence. A field has its borders; it has some limits. The house has walls as barriers and only the deserving one is allowed to come in.
We may add that this is also the difference between a pillar and an altar: the pillar consists of one stone and is parallel to the general call aiming to notify that there is a Master of the world. The altar consists of many stones and it is suitable for the nation that has got detailed Divine guiding and all the details of its life are illuminated by Divine light by Torah and Mitzvoth.
Lessons
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