In the second part of this letter, Lewis brings up the question of praying to or with saints. While there is certainly a discussion of such topics in Jewish prayer I'm not going to rehash it. I'm simply going share my thoughts. So, if you don't like what I write below - blame it on me, there are other opinions out there...
A fundamental belief in Judeo-Christian thought is that man is created in God's image. This can and does mean a number of things. But, chief among them, is that any individual human can have a direct relationship with God. No intermediary is necessary. And while it might feel like a good idea to have an mutual friend between you and God, it seems to me that it's a bit of a trap. God already told us you can have a direct relationship. He's not lying, so trust him! So, no, I don't like the idea of praying to saints (or righteous individuals, or rabbis, or angels, etc.).
Still, there are several points to note. First, the above does not mean that one should not have others pray for them. Of course you should. That's why synagogues (and I assume churches) have special prayers for the those who may be sick or in danger, as we did for the hostages and continue to for the members of the U.S. Military and Israeli Defense Force. When someone prays for you, they declare before God that they care and that they themselves would be harmed should something happen to you. They throw in their peace of mind and well-being and say, "God, I am unworthy, but know that harming them hurts me too." This empathy is of great importance before God and may tip the scale in favor of safety and salvation for the person being prayed for.
Second, though there is a lot of discussion as to how much angels should be invoked in prayer, it's almost impossible to cancel them completely from the Jewish liturgy. Angels, as in the typical type that are pictured with wings, and the astronomical bodies such as the sun and stars, have no free will. They follow the will of God. Copying their songs of paise to God or mimicking aspects of their being in physical terms (such as standing with ones feet together since angels are described as having one leg, or wearing white) demonstrates that we heed, or at least stive to heed, God's will like the angels, despite both our capability to to not follow and our sometimes unfortunately choices to not not follow His commands.
Third, the place of prayer matters. Certain places are holy because of what happened there or what is to be found there. For example, Jerusalem is holy because it is where Abraham did not end up sacrificing Isaac, or because it is the place God chose to build the Temple (one could argue that God commanded to build the Temple is Jerusalem because it was already holy - perhaps due to the just mentioned binding of Isaac. But I don't think you have to say that. There are other rationales given for why the Temple is, for example, on the border between the tribes of Judah and Benjamin). Other places, such as a typical synagogue outside of Israel, can become holy, and appropriate for prayer, simply because Jews have prayed there for so long. And, perhaps a place can become holy, or let us say consecrated, because it is the final resting place of great people or a place where great people did their holy work. Abraham Lincoln put it succinctly, "The brave men, living and dead, who struggled here, have consecrated it, far above our poor power to add or detract." Praying in a place of holiness (beyond perhaps that God is 'attracted' to such places) shows that we recognize the holiness. That we too, strive to be holy and walk in the footsteps of the great ones before us.
In summary, I certainly don't like the idea of praying to saints and I'm not a big fan of praying with saints but I'm willing to entertain some glimmers of the idea as with my caveats above.
Next time we'll discuss time of prayers...