David Galenson makes this interesting point about Pablo Picasso in his paper on artists and the art market published in the American Enterprise Institute’s journal, The American. It turns out Picasso had a clever scheme for raising his profile among collectors: paint a lot of dealers:
It is likely that no artist painted more portraits of dealers. During the early period in which he was establishing himself as a leading artist, Picasso painted the dealers Pedro Manach (1901), Clovis Sagot (1909), Ambroise Vollard (1910, 1915), Daniel-Henry Kahnweiler (1910), Wilhelm Uhde (1910), Léonce Rosenberg (1915), André Level (1918), Paul Rosenberg (1919), and Berthe Weill (1920). In 1918, he also painted portraits of the wife of Georges Wildenstein and of the wife and daughter of Paul Rosenberg.11
Early in his career, Picasso told Kahnweiler, “I’d like to live like a poor man with a lot of money.”12 Yet Picasso was careful to keep private his considerable interest in the material rewards of art, and it did not become part of the colorful image that made him the epitome of the modern artist for a vast admiring public.
Arti$ts and the Market (The American)