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“The very act of saying I think there should be other parties in the country — that’s where the line was totally crossed, was ruptured,” Mr. Oliva said in an interview at his home studio.

Mr. Milanes has often tested the limits of what officials will swallow. In a 2008 interview with the Spanish newspaper, Publico, he suggested that Raul Castro is too old to run Cuba.

“I don’t trust in any Cuban official who is more than 75 years old,” he said.

Earlier this year, he told journalists in Florida that a dissident group has a right to protest.

“The most vile and cowardly thing is for a horde of supposed revolutionaries to ruthlessly attack [them],” Mr. Milanes wrote. This “does not mean I disagree with Fidel (Castro),” he added.

A column on state-run website, Cubadebate, chided Mr. Milanes for what it called his erratic opinions and speculated he was suffering a deep personal crisis. But officials have not moved to stop the international star from giving concert tours around the world.

Mr. Milanes, who has written odes to the comminist rebel Che Guevara, still clearly considers himself a socialist.

“My 53 years of revolutionary militancy give me the right, which very few exercise in Cuba, to express myself with the freedom that my principles require,” he said.

Cuban media may have given a hint of one line not to cross when the newspaper, Trabajadores, published an interview with Mr. Rodriguez in which he urged a more democratic socialism, eased restrictions on travel, better environmental protection and less discrimination.

The complete transcript later posted on Mr. Rodriguez’s blog showed Trabajadores had cut some of his more controversial sentiments, such as: “I hope if someone protests for something that we don’t agree with, we have enough dignity to respect their right to express themselves.”

Cuba has a deeply ingrained “fortress-under-siege” hostility to speech that might give ammunition to the enemy dating back to the struggle to break free from Spain in the 1890s, Mr. Lopez said.

That bunker mentality sharpened after the 1959 Cuban Revolution and the start of U.S. efforts to oust Fidel and Raul Castro. Officials often say the need to present a united front justifies the prohibition of a free local media on the island.

“Prevention of expressing certain views is not only tolerated but, I would say, supported by the general population” in a way that seems unfamiliar to Americans who cherish their First Amendment rights, Mr. Lopez said.

“I can’t think of a time in the United States when somebody came to me and said: ‘You know what, this is true but he shouldn’t have said it.’ It’s very unusual.”

Fidel Castro expressed the principle in a 1961 warning to Cuba’s intellectual class that excessive criticism would not be tolerated.

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