Drawn in 1916, this drawing represents a clothed spanish man, wearing a hat, with his hands crossed. It is a wonderful example of Modigliani's subte pencil work and unique style. The year marks the beginning of Modigliani's most prolific period, which will end in 1920 upon his death. A similar work now belongs to the collection of the Museum of Modern Art, in New York: Mario the Musician. Born in 1884, in Livorno, Modigliani began to study painting in 1898, and attented the Reale Instituto di Belle Arti in Venice in 1903. His major influences were Cezanne and Toulouse- Lautrec, altough he quickly developped his own style, influenced by his arrival in Paris, and his bohemin way of life. He became a current exhibitor in the Salon d'Automne and the Salon des Indépendants between 1907 and 1912. Experimenting with painting, and then with sculpture after meeting Constantin Brancusi in 1909, Modigliani's subject of choice remains portraiture throughout his artistic creation. Mostly living in poor conditions, Modigliani will have a few, but important, patrons. First, the collector Dr. Paul Alexandre, then his dealers Paul Guillaume and Leopold Zborowski. Only one solo show will be organized during his lifetime, at the Galerie Berth Weill in December of 1917, by Leopold Zborowski. In 1916, he is still represented by Paul Guillaume and spending most of his time with his artistic cirle in Paris. Those include important art historical figures such as Max Jacob, Jacques Lipchitz and Chaim Soutine. His subject often include people from his entourage: lovers, friends, wives, children... In the case of Caballero, the sitter's identity is not identified. Ten years after his arrival to Paris, 1916 is an important year in the artist's production. Numerous of Modigliani's most iconic works were painted throughout 1916. The most iconic perhaps, remains the double portrait of Jacques and Berthe Lipchitz, now in the Art Institute of Chicago and an astonishing depiction of the poet Max Jacob in a top hat and polka dot cravat, which now hangs in Dusseldorf's Kunstsammlung Nordrhein-Westfalen. Modigliani had been living in Montparnasse for almost a decade and had been one of the main figures in the jewish immigrants settling in the neighborhood. To celebrate his marriage to Russian poet Berthe Kitrosser, Lipschitz had commissioned this portrait to help Modigliani financially. The cost of which was described by Lipschitz as: « ten francs per sitting and a little alcohol ». The portrait of Max Jacob draws similarities with the drawing presented in this catalogue. From the composition to the subject, Caballero can draw a parallel to one of Modigliani's most masterful portrait. Caballero, a work that the gallery has known of for over thirty years, has been included in several of Modigliani's most important exhibitions over the past two decades, most notably at the Palazzo Reale in Milano (2003), the Musée du Luxembourg in Paris (2003), the Jewish Museum in New York (2004) and the Art Gallery of Ontario (2005). It first belonged to Youki Desnos, a central figure in the Montparnasse of Modigliani. Lucie Badoud, of her original name was the lover of Foujita for several years before marying the surrealist poet Robest Desnos.