The Kokoschka literature often accepts the claims spread by the artist himself, namely, that the only definitive factors informing his choice of models were personal sympathy and human values. Yet how much calculation could be hidden behind this has previously been overlooked or concealed. Many times Kokoschka pursued only his financial interests; thus, for example, in 1951, he portrayed Emil Bührle, founding owner of the leading Swiss armaments corporation. In a letter to Hugo Feigl , Kokoschka indeed called Bührle „one of the biggest armament kings,“ yet justified his work on his portrait with the argument that he must pay for the roof of his „future little house.“ Kokoschka also dispensed middlemen to establish contact with politicians. Assisted by art historian Hans Wingler, who knew the daughter of Adenauer, Kokoschka attempted to convince the Chancellor of a portrait sitting. Previously unknown, is that in 1941 London, Kokoschka together with art historian Carl Tancred Borenius sought in vain to paint Churchill. Likewise, an attempt to portray Pope Pius XII also failed. The paper draws upon extensive unpublished Kokoschka letters among his papers in the Zentralbibliothek, Zürich.