I draw my title and theme from a passing observation in a recent analysis of Santayana's views of American culture by Krzysztof Piotr Skowronski." Skowronski contrasts "confrontation" with "encounter," understanding the latter as "a transfer of ideas and experiences that can serve the intellectual, spiritual, or economic developments of at least one of the parties."" Confrontation, on the other hand, consists in "a clash of interests or ideas resulting in a kill-or-be-killed scenario."" I contend that Santayana's critique of American philosophy and culture is encountering in the manner described by Skowronski, and thus ought not be grouped, as Robert Dawidoff has it, amongst those confrontational "American Tocquevillian" critiques of Henry Adams and Henry James." Two larger aims of my discussion are to obviate attempts to dismiss Santayana's thinking as a form of "outsider cynicism," and to invite a serious consideration for whether and in what respects his critique of American philosophy and culture avoids the shortcomings of anti-relationality and disconnection that are discussed in another presentation of this same panel."
In order to flesh out Santayana's encounter with American philosophy and culture, it is necessary to place the critique in the larger scheme of his broad historical perspective." More specifically, Santayana's understanding of James, Royce, and Dewey rely heavily on his philosophical critique of Modern methodologies." Thus, I begin with a seminal passage from one of the volumes of Santayana's early influential work, The Life of Reason, which finds Santayana engaging the modi operandi of Hobbes, Locke, Berkeley, and Hume."
As to Santayana's understanding of American culture, his much discussed critique (and coining) of the "genteel tradition" can be shown to flow directly from his philosophical critique of Modern methodologies, and so I turn in the second part of my presentation to a consideration of this critique." More specifically, I bring out the sophistication of Santayana's identification of Calvinism and Transcendentalism as the twin ingredients of the Genteel Tradition." In all of these respects it is my intent to demonstrate the links between Santayana's sophisticated philosophical insights, and his informal, speculative criticisms of America and its philosophy.
Finally, I consider the numerous published, and unpublished attempts to cast Santayana as, to borrow the term from Anthony Woodward in his characterization of one of the main characters in Santayana's only novel, a cynical "fain"ant."" It is one of the more remarkable shortcomings of contemporary American philosophy that it has chosen to allow, and sometimes encourage this characterization of Santayana when a more accurate understanding would open the way for a broader, mutual edification on behalf of American intellectuals and those who criticize them." At stake in all of this is a clarification of the power and importance of critique, and the clear delineation between its fruitful and stultifying instantiations.
 Krzysztof Piotr Skowroński." "Santayana and the Problem of Americanization." Transactions of the Charles S. Peirce Society." Winter, 2004, Vol. XL, No. 1: 107-133.
 Ibid, 108.