His answer is the best you'll hear on the topic...

Mitch Horowitz: No. He’s a genius who has a very shrewd eye for kind of oppositional imagery in our culture. And he uses these things and he understands the magnetism of these symbols. You know, symbols like the pentagram and the eye in the pyramid or astrological symbols, they do have a certain magnetic power. They have a pull on us. When people look at a crucifix or when people look at a Star of David, they feel something. There’s some kind of pull. It may just be a matter of conditioning, but the fact is, when you use the eye in the pyramid, it’s a magnetic symbol. It possesses something.

And I think when you’re using imagery that comes from the ancient world or that comes from Renaissance-era occultism, there is a little something going on there. We’ve never quite figured out a way to digest the image of the pentagram. Some people are really attracted to it, other people recoil from it. Jay-Z understands this and when he uses these images in his videos, on his clothing, and in other places, you know, he realizes that we are people who think in images and that you can take an image and you get a response from people. I was asked at one point whether I thought Jay-Z was a Freemason because of some of the images that appear in his videos. One of his videos also shows an image of Mao Tse Tung, I don’t think he’s an Agrarian Socialist, but he understand in the same way that street artists do that you can take these images and they touch an emotional cord in us that sometimes is very subliminal, even mysterious.

I don’t think he’s an occultist, but I do think he is probably a genius in terms of using imagery.

Source: Big Think