Bosch was also sporadically drawn into Cuban politics. Infuriated by the rapacious corruption of "more or less honestly" elected president Gerardo Machado, the short, fiery-tempered businessman backed an uprising in 1931 and had to flee the island once the rebellion collapsed. Years later, in 1950, Bosch was persuaded to serve briefly as finance minister and managed to put the budget into the black in little more than a year, but corruption returned as soon as he left the post. The Bacardi family then collided with the Batista regime, which used the national labor federation to stir up trouble and attempt to extort money from the company.
In an often overlooked part of Cuban history, Bosch and other Bacardi family members supported the Cuban revolutionaries, including Fidel Castro and the broader M-26-7 organization. It is unlikely that Castro's revolution would have succeeded without the wide middle-class support that it enjoyed, a reaction against the brutal repression of the Batista regime and its thugs. Gjelten recounts that Bosch personally donated at least $38,500 (equivalent to $275,000 today) and arranged meetings between the revolutionaries and the CIA to assuage the latter's concerns. Other Bacardi family members, employees and facilities were also put at the service of the underground.
The Bacardis opposed Cuban dictator Fulgencio Batista and supported Fidel Castro, even granting some workers leave to join his rebel forces. Vilma Espin, late wife of Cuban President Raul Castro, was the daughter of a Bacardi accountant and one Bacardi family member even knitted caps and stockings for Castro rebels fighting Batista's forces.
The rebels issued a decree that Bacardi facilities were not to be attacked, and the company's chief executive, Jose "Pepin" Bosch, accompanied Castro on his first trip to the United States after taking power in 1959. Bosch ducked out early, however, already afraid of where Castro was leading the government.
After nationalizing Bacardi, Cuba eventually began producing Havana Club rum, a brand it usurped from the Arechabala family, Bacardi competitors who did not fight to keep their trademarks after nationalization.
Bacardi eventually bought the naming rights to Havana Club from the Arechabalas and began selling its own version of Havana Club in the United States, touching off more legal battles with Cuba that have yet to be fully resolved.