Having already acquired several important paintings by Picasso, Leo Stein and his sister Gertrude finally met the painter through the dealer Clovis Sagot in the fall of 1905. That winter Picasso began to work on his famous portrait of Gertrude (C. Zervos, vol. I, no. 525), and in early 1906 he painted a portrait in gouache of Leo.
Fernande Olivier, Picasso's mistress during this time, described the Steins:
They made a pair. He with a professional air, bold, wearing gold-rimmed glasses. A long beard with reddish highlights, a shrewd eye, a large, stiff body given to strange positions and unfinished gestures... Much too intelligent to mind ridicule, and too self-confident to bother with what others thought, they were rich, and he wanted to paint... (quoted in P. Daix and G. Boudaille, Picasso: The Blue and Rose Periods, Neuchâtel, 1967, p. 284)