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Paul Guillaume was twenty-three when Modigliani painted this portrait. Already an established dealer in l'art négre, Guillaume is presented as the 'new helmsman' and defender of contemporary art. His name boldly appears at upper left; at upper right the Star of David is accompanied by the inscription 'Stella Maris'; 'Novo Pilota' is painted with a flourish at lower left. Modigliani signed the painting at lower right, adding a 'swastika' which, prior to its later negative association, was recognised as a Sanskrit symbol meaning 'good omen'.

The Russian sculptor Ossip Zadkine, a friend of Modigliani, gave an account of one of Guillaume's sittings for the artist: 'Zborowski took Modi to the home of Paul Guillaume, a young art dealer, rather plump and flabby, who exhibited not only cubist paintings but also African sculptures as yet unfamiliar to the general public, of the sort I had noticed some years earlier in the British Museum, with ethnographic labels. Paul Guillaume agreed to have his portrait done by Modigliani. All the sittings and painting sessions took place in a cellar lit by strong electric light and with a litre of wine on the table'.