While identified with the modernist movements in art and literature, Stein's political affiliations were a mix of reactionary and progressive ideas. She was outspoken in her hostility to some liberal reforms of progressive politics. To Stein, the industrial revolution had acted as a negative societal force, disrupting stability, degrading values, and subsequently affecting cultural decline. Stein idealized the 18th century as the golden age of civilization, epitomized in America as the era of its founding fathers and what was in France, the glory of its pre-revolutionary Ancien Régime. At the same time, she was pro-immigrant, pro-democratic, and anti-patriarchal. Her last major work was the libretto of the feminist opera The Mother of Us All (1947) about the socially progressive suffragette movement and another work from this time, Brewsie and Willie (1946), expressed strong support for American G.I.s.
A compendium of source material confirms that Stein may have been able to save her life and sustain her lifestyle through the protection of powerful Vichy government official Bernard Faÿ. Stein had met Fay in 1926, and he became her "dearest friend during her life", according to Alice B. Toklas. Faÿ had been the primary translator of Stein's work into French and subsequently masterminded her 1933–34 American book tour, which gave Stein celebrity status and proved to be a highly successful promotion of her memoir, The Autobiography of Alice B. Toklas. Fay's influence was instrumental in avoiding Nazi confiscation of the Stein's historically significant and monetarily valuable collection of artwork, which throughout the war years was housed in Stein's Paris rue Christine apartment, under locked safeguard.
In 1941, at Faÿ's suggestion, Stein consented to translate into English some 180 pages of speeches made by Marshal Philippe Pétain. In her introduction, Stein crafts an analogy between George Washington, and Pétain. She writes of the high esteem in which Pétain is held by his countrymen; France respected and admired the man who had struck an armistice with Hitler. Conceived and targeted for an American readership, Stein's translations were ultimately never published in the United States. Random House publisher Bennett Cerf had read the introduction Stein had written for the translations and been horrified by what she had produced.
Of Jewish parentage, Stein collaborated with Vichy France, a regime that deported more than 75,000 Jews to Nazi concentration camps, of whom only 3 percent survived the Holocaust. In 1944, Stein wrote that Petain's policies were "really wonderful so simple so natural so extraordinary". This was Stein's contention in the year when the town of Culoz, where she and Toklas resided, saw the removal of its Jewish children to Auschwitz. It is difficult to say, however, how aware Stein was of these events. As she wrote in Wars I Have Seen, "However near a war is it is always not very near. Even when it is here." Stein had stopped translating Petain's speeches three years previously, in 1941.
Stein was able to condemn the Japanese attack at Pearl Harbor while simultaneously maintaining the dissonant acceptance of Hitler as conqueror of Europe. Journalist Lanning Warren interviewed Stein in her Paris apartment in a piece published in The New York Times Magazine on May 6, 1934. Stein, seemingly ironically, proclaimed that Hitler merited the Nobel Peace Prize.
- "The Saxon element is always destined to be dominated. The Germans have no gift at organizing. They can only obey. And obedience is not organization. Organization comes from community of will as well as community of action. And in America our democracy has been based on community of will and effort.... I say Hitler ought to have the peace prize...because he is removing all elements of contest and struggle from Germany. By driving out the Jews and the democratic Left elements, he is driving out everything that conduces to activity. That means peace."
Given that after the war Stein commented that the only way to ensure world peace was to teach the Germans disobedience, this 1934 Stein interview has come to be interpreted as an ironic jest made by a practiced iconoclast hoping to gain attention and provoke controversy. In an effort to correct popular mainstream misrepresentations of Stein's wartime activity, a dossier of articles by critics and historians has been gathered for the online journal Jacket2.
How much of Stein's wartime activities were motivated by the real exigencies of self-preservation in a dangerous environment, can only be speculated upon. However, her loyalty to Pétain may have gone beyond expedience. She had been urged to leave France by American embassy officials, friends and family when that possibility still existed, but declined to do so. Accustomed to a life of entitlement since birth, Stein may have been convinced her wealth and notoriety would exempt her from what had befallen other European Jews. In an essay written for the Atlantic Monthly in November 1940, Stein had written about her decision not to leave France: "it would be awfully uncomfortable and I am fussy about my food." Stein continued to praise Pétain after the war ended, this at a time when Pétain had been sentenced to death by a French court for treason.
Author Djuna Barnes provided a caustic assessment of Stein's book, "Wars I Have Seen":
- "You do not feel that she [Stein] is ever really worried about the sorrows of the people. Her concerns at its highest pitch is a well-fed apprehension."
Others have argued that some of the accounts of Stein's war time activities have amounted to a "witch hunt".