During the country's Student’s Week in 1928, Otero Silva formed part in a series of protests against the rule of dictator Juan Vicente Gómez (see Generation of 1928 ).

There, along with Gustavo Machado, Rafael Urbina López and other Venezuelan expatriates he participated in the taking of Fort Amsterdam in Willemstad on June 29 of the same year, in another attempt to overthrow president Gómez.

[1] The plot, supported by 250 men, in addition to notable communists [1] such as José Tomás Jiménez and Guillermo Prince Lara, involved the kidnapping of governor Leonard Albert Fruytier [nl].

[1] The revolutionaries plundered the island's weapons, ammunition and treasury[2] and hauled governor Fruytier back to Venezuela on board the stolen American ship Maracaibo.

Taking advantage of the freedom of speech allowed by Gómez's successor, Eleazar López Contreras, Otero Silva published humorous political poetry in newspapers.

[3] Once back in Venezuela, he co-founded the humorous weekly newspaper El Morrocoy Azul (The Blue Tortoise), along with Francisco José Delgado and Claudio Cedeño.

Towards the end of the dictatorship, Otero Silva was arrested for editing and publishing the Manifiesto de los Intelectuales (Intellectuals Manifesto), a text attacking Pérez Jiménez' administration.

After Marcos Pérez Jiménez was overthrown in 1958, Otero was awarded with the National Prize for Journalism, and elected to the Venezuelan Senate, representing the state of Aragua.