Mr. Kimball, I believe you are oversimplifying Santayana’s politics.

First of all, you are using the “history” quote out of context. However, most people who use it do this, so it is understandable.

Second, you are quoting the letter out of context. If you printed the previous paragraph of the letter, it would not go down so well with your readers:

As you probably know, I am (strange as it may be nowadays) a naturalist in natural philosophy. I cannot conceive the existence of moral life, or of anything good, not rooted in some definite material organism, animal or social. On this point I agree with the historical materialism of Marx. I also agree with the theory of Fascism, in so far as this coincides with the politics of Plato and of antiquity in general. Society is not based
on ideas, but on the material conditions of existence, such as agriculture and defence; virtue is moral health, and when genuine rests on the same foundations.

What Santayana was mostly opposed to was radical democracy, on the principle that it would entail imposing the will of the majority on the individual, rather than affirming a rational order rooted in tradition. This is the conservative side of Santayana that Russell Kirk emphasized.