Soon thereafter, Stein introduced Toklas to Pablo Picasso at his studio, where he was at work on Les Demoiselles d'Avignon.
In 1908, they summered in Fiesole, Italy, Toklas staying with Harriet Lane Levy, the companion of her trip from the United States, and her housemate until Alice moved in with Stein and Leo in 1910. That summer, Stein stayed with Michael and Sarah Stein, their son Allan, and Leo in a nearby villa. Gertrude and Alice's summer of 1908 is memorialized in images of the two of them in Venice, at the piazza in front of Saint Mark's.
Toklas arrived in 1907 with Harriet Levy, with Toklas maintaining living arrangements with Levy until she moved to 27 Rue de Fleurus in 1910. In an essay written at the time, Stein discussed the complex efforts humorously, involving much letter writing and Victorian niceties, to extricate Levy from Toklas' living arrangements. In "Harriet", Stein considers Levy's nonexistent plans for the summer, following her nonexistent plans for the winter:She said she did not have any plans for the summer. No one was interested in this thing in whether she had any plans for the summer. That is not the complete history of this thing, some were interested in this thing in her not having any plans for the summer... Some who were not interested in her not having made plans for the summer were interested in her not having made plans for the following winter. She had not made plans for the summer and she had not made plans for the following winter... There was then coming to be the end of the summer and she was then not answering anything when any one asked her what were her plans for the winter.
During the early summer of 1914, Gertrude bought three paintings by Juan Gris: Roses, Glass and Bottle, and Book and Glasses. Soon after she purchased them from Daniel-Henry Kahnweiler's gallery, the Great War began, Kahnweiler's stock was confiscated and he was not allowed to return to Paris. Gris, who before the war had entered a binding contract with Kahnweiler for his output, was left without income. Gertrude attempted to enter an ancillary arrangement in which she would forward Gris living expenses in exchange for future pictures. Stein and Toklas had plans to visit England to sign a contract for the publication of Three Lives, to spend a few weeks there, and then journey to Spain. They left Paris on July 6, 1914 and returned on October 17. When Britain declared war on Germany, Stein and Toklas were visiting Alfred North Whitehead in England. After a supposed three-week trip to England that stretched to three months due to the War, they returned to France, where they spent the first winter of the war.
With money acquired from the sale of Stein's last Matisse Woman with a Hat to her brother Michael, she and Toklas vacationed in Spain from May 1915, through the spring of 1916. During their interlude in Majorca, Spain, Gertrude continued her correspondence with Mildred Aldrich who kept her apprised of the War's progression, and eventually inspired Gertrude and Alice to return to France to join the war effort.
Toklas and Stein returned to Paris in June 1916, and acquired a Ford automobile with the help of associates in the United States; Gertrude learned to drive it with the help of her friend William Edwards Cook. Gertrude and Alice then volunteered to drive supplies to French hospitals, in the Ford they named Auntie, "after Gertrude's aunt Pauline, 'who always behaved admirably in emergencies and behaved fairly well most times if she was flattered.'"
During the 1930s, Stein and Toklas became famous with the 1933 mass market publication of The Autobiography of Alice B. Toklas. She and Alice had an extended lecture tour in the United States during this decade. They also spent several summers in the town of Bilignin, in the Ain district of eastern France situated in the picturesque region of the Rhône-Alpes. The two women doted on their beloved poodle named "Basket" whose successor, "Basket II", comforted Alice in the years after Gertrude's death.
With the outbreak of World War II, Stein and Toklas retreated to the town of Culoz. After the war, Stein was visited by many young American soldiers. The April 6, 1945 issue of Life magazine featured a photo of Stein and American soldiers posing in front of Hitler’s bunker in Berchtesgaden. They are all giving the Nazi salute and Stein is wearing the traditional Alpine cap, accompanied by the text: “Off We All Went To See Germany.”
In a preface written for a Paris exhibition of Spanish painter Francisco Riba Rovira in 1945— approximately one year before her death—she expressed her opinions of Picasso, Cézanne, Matisse and Juan Gris as well as Riba-Rovira, a familiar artist of her salon at rue de Fleurus.
The following is a translation from Stein's preface to the exhibition by Francisco Riba Rovira at Roquepine Gallery in May 1945:It is inevitable that when we really need someone we find him. The person you need attracts you like a magnet. I returned to Paris, after these long years spent in the countryside and I needed a young painter, a young painter who would awaken me. Paris was magnificent, but where was the young painter? I looked everywhere: at my contemporaries and their followers. I walked a lot, I looked everywhere, in all the galleries, but the young painter was not there. Yes, I walk a lot, a lot at the edge of the Seine where we fish, where we paint, where we walk dogs (I am of those who walk their dogs). Not a single young painter!
One day, on the corner of a street, in one of these small streets in my district, I saw a man painting. I looked at him; at him and at his painting, as I always look at everybody who creates something I have an indefatigable curiosity to look and I was moved. Yes, a young painter!
We began to speak, because we speak easily, as easily as in country roads, in the small streets of the district. His story was the sad story of the young people of our time. A young Spaniard who studied in fine arts in Barcelona: civil war; exile; a concentration camp; escape. Gestapo, another prison, another escape... Eight lost years! If they were lost, who knows? And now a little misery, but all the same the painting. Why did I find that it was him the young painter, why? I visited his drawings, his painting: we speak.
I explained that for me, all modern painting is based on what Cézanne nearly made, instead of basing itself on what he almost managed to make. When he could not make a thing, he hijacked it and left it. He insisted on showing his incapacity: he spread his lack of success: showing what he could not do, became an obsession for him. People influenced by him were also obsessed by the things which they could not reach and they began the system of camouflage. It was natural to do so, even inevitable: that soon became an art, in peace and in war, and Matisse concealed and insisted at the same time on that Cézanne could not realize, and Picasso concealed, played and tormented all these things.
The only one who wanted to insist on this problem, was Juan Gris. He persisted by deepening the things which Cézanne wanted to do, but it was too hard a task for him: it killed him.
And now here we are, I find a young painter who does not follow the tendency to play with what Cézanne could not do, but who attacks any right the things which he tried to make, to create the objects which have to exist, for, and in themselves, and not in relation.This young painter has his weaknesses and his strengths. His force will push him in this road. I am fascinated and that is why he is the young painter who I needed. He is Francisco Riba Rovira.
In the 1980s, a cabinet in the Yale University Beinecke Library, which had been locked for an indeterminate number of years was opened and found to contain some 300 love letters written by Stein and Toklas. They were made public for the first time, revealing intimate details of their relationship. Stein’s endearment for Toklas was “Baby Precious,” in turn Stein was for Toklas, “Mr. Cuddle-Wuddle.”
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