[1] In 1905, after graduating the military academy, he briefly attended the San Fernando school in Havana, where he was tutored by Ricardo de la Torriente and Leopoldo Romañach.

[9] After returning to the island in 1908, Massaguer began mingling with Havana's aristocratic circles, forming close friendships with some of the city's most powerful and influential men, as well as winning the favor of many women who were quickly charmed by him.

[5] Massaguer, largely self-taught, honed his style using the avant-garde techniques he studied from the European and American magazines that were widely available in Cuba at the time.

After two years of refining his craft, Havana announced a poster contest aimed at attracting North American tourists to stay in the city during the winter months.

[5] The prize was ultimately awarded to the Galician painter Mariano Miguel, who had recently married the daughter of Nicolás Rivero, the wealthy owner of the conservative newspaper Diario de la Marina.

Although Massaguer received only an honorable mention, the fraud scandal caused such an uproar that his name quickly entered the public spotlight, and he became an overnight sensation.

[9] Other exhibitors here included Maribona, Riverón, Portell Vilá, Valer, Botet, Barsó, García Cabrera, Carlos Fernández, Rafael Blanco, and Hamilton de Grau.

[11] Social catered to a certain aesthetic in Cuba - that of the sophisticated elite socialite - but Massaguer would also use this magazine to ridicule and jibe against that same class of society when he found their personalities worthy of his contempt.

[12] In Social, readers could find a variety of content, including short stories, avant-garde poetry, art reviews, philosophical essays, and serialized novels, as well as articles on interior design, haute couture, and fashion.

[5] One of the features of Social magazine was its section called "Massa Girls," which was a play on his own name, and pronounced with a glottal 'g' in a similar fashion to the letter in Massaguer.

His broad, childish laugh, of a carefree individual who carries his luck hidden in a pocket, appears everywhere for the moment, disguising the pranks of pupils that lurk, mock and, finally, flash with satisfaction at finding the characteristic point after having analyzed a soul... Massaguer's personality is beginning to solidify now.

He has been the best-known and most popular caricaturist for a long time, but his technique had not reached the security, the mastery of values that he presents in his latest works, which is very natural and explainable”[5]In 1919, Massaguer and his brother created the magazine Carteles.

[13] It became a prime example of the humor and graphic design employed by artists like Horacio Rodríguez Suria and Andrés García Benítez to reflect on Cuban society and politics.

[5] In April, 1921, Cinelandia quoted the Argentinian Columbia University professor, Enrique Gil: "[Latin American] merchants have the movies as guides.

[9] In the introduction to Guignol, Massaguer wrote: “Sometimes a tight shoe, a flowery buttonhole, a peculiar movement when walking, reveals the soul of the model...

The tendency of those of us who follow the modern school of caricature is to simplify by exaggeration”[5]In 1924, he moved to New York with his wife, the niece of Mario García Menocal.

[9] In the late 1920s, Massaguer made the mistake of creating an unflattering caricature of the Cuban dictator Gerardo Machado - and was deported from the country.

He particularly enjoyed being free again to travel to Cuba in order to legally purchase and partake in the alcoholic beverages of Havana's clubs - whereas Prohibition in the United States ended in the same year as the fall of Machado.

[9] He was visited regularly and interacted with the New York social elite, and many Cuban exiles, including Pablo de la Torriente Brau and Teresa Casuso Morín.

[8] One of Massaguer's most famous works from this period is one of Camilo Cienfuegos, Che Guevara, and Fidel Castro and a dove perched on one of their shoulders.

[9] In 1989, on the Centenary of his birth, the Cuban Museo Nacional de Bellas Artes featured an exhibition on Massaguer, and brought the artist to life once again in the communist country.

[8] His works have also been featured at the Palacio de los Capitanes Generales, the City Museum of Havana, and the Cárdenas Art Gallery.

The Franklin D. Roosevelt Presidential Library and Museum maintains stewardship of certain historical works of Massaguer that caricatured the President in an unflattering manner during the Great Depression.