[citation needed] At the end of the 1920s he met poet Adriano del Valle and in 1930, Daniel Vázquez Díaz, when he was painting frescoes in La Rábida monastery.
He met Alberto Sánchez, Pablo Neruda, Rafael Alberti, Miguel Hernández, Maruja Mallo, Joaquín Torres García and Luis Buñuel.
In 1935 Caballeros created three surrealist posters for his performance together with del Valle in the Ateneo of Sevilla and illustrated poems for Lorca and Neruda.
He contributed to magazines such as Cruz y Raya, Noreste, Línea, Caballo Verde para la poesía, (Green Horse for Poetry) etc.
After the war he made surrealist illustrations filled with contents related to Catholicism in magazines such as Vértice or Santo y Seña convinced by Dionisio Ridruejo.