When you build the tallest building on the NY skyline, and build 2 of them side by side, then you are making a statement by that simple fact alone, regardless of design and appearance. Your statement is "I want this to be the most important building complex in this city." Those buildings, dominating the skyline, then become a visual image, or symbol for some, of the city itself.
The reason that the terrorists attacked the WTC is because it symbolizes NY, not because of what was going on inside. If they hated stockbrokers, they could target the NYSE. If they hated insurance, they could bring down a building that housed a big insurance company. If they didn't like usurers, they could bring down a bank building. But the WTC had firms in all those industries and more. It wasn't an attack on any specific business, it was an attack on New York. They couldn't blow the whole damn city up, so they went for the biggest thing in New York they could destroy, that's all.
What the buildings symbolize must depend on what their purpose is. Is it a jail? A seat of government? A library? A university? An apartment building? What the building qua building symbolizes depends on what goes on inside. How could Tolkien be so stupid as to consider a tall collection of offices as symbolic of Tyranny, unless he hated commerce in general?
I have never read these books, and never studied Tolkien, but from what I have learned about Tolkien's background, it appears that he was principled in his defense of core western values. Dreher's assumption that Tolkien would have considered the WTC a symbol of tyranny offends me, because I think it shows a great writer in a bad light without factual basis.
You are confusing the WTC as a symbol of NYC because of its place on the skyline, with its symbolism based upon on its function as an office building. Dreher seemed to be implying that because it is a place where trade was conducted, it is a symbol of tyranny. That is crap, IMO, and if Tolkien would have thought such, he would have been full of crap. I think Dreher is the one full of crap, though, not Tolkien.
As I said, otherwise an excellent article. I don't know why he felt the need to put in this attack on Tolkien's logic.