The essay reconstructs the controversial relationship between Bernard Berenson and Jean Cocteau, from their first meeting in 1916 to the post-World War II period, through detailed and largely unpublished archive documentation. Thus, on the one hand, Berenson's `uncertainties' in the face of contemporary art, in particular Cubism and Picasso, are brought into sharper focus, and on the other hand, almost specularly, the impatience of Cocteau and some personalities close to him, such as Gertrude Stein and Marie Laure de Noailles, towards this closure, culminating in some episodes of mockery and discrediting of the American critic's authority.