This essay examines Pirandello’s tortuous relationship with the United States as it emerges in his personal experiences and in his literary works. In spite of the triumphal welcome Pirandello received on his visits to the United States in 1923 and 1935, his attitude toward the country was fraught with skepticism and ambivalence. Unsettled by the threat of US neo-colonization of lands and cultures, and associating American civilization with blind enthusiasm for technology unaccompanied by a concomitant moral growth, Pirandello expressed his scarce admiration for a country and a people whose favor and financial support he nonetheless hoped to gain. In Pirandello’s fiction, America is a place whose opportunities come at the price of loneliness, exploitation, and difficult compromises. The essay also delves into Pirandello’s reception in the New World in the 1930s, a time that required him to articulate his position on Fascism before an American audience.