BY ALFONSO CHARDY AND JAY WEAVER

Rafael del Pino Siero, a U.S. citizen, was one of Fidel Castro's first friends at the University of Havana -- and one of the first former allies Castro imprisoned after taking power in 1959.

Del Pino Siero, who had broken with the guerrilla leader over suspicions that Castro was a communist, was captured while trying to help a Cuban escape to Miami in July 1959. He died in his prison cell 18 years later at age 51, leaving behind in Miami two youngsters: Rafael del Pino Jr. and his sister Milagros Suárez.

The Del Pino children got a measure of justice Friday when six Miami-Dade County jurors gave them the biggest award to date in a wrongful death claim against the Cuban government: almost $253 million.

The amount eclipsed the $187.6 million awarded by a federal judge to the relatives of three victims in the 1996 shootdown of two Brothers to the Rescue small planes by a Cuban MiG. Family members in that case collected about half of the award from frozen Cuban assets in New York.

The Del Pino children probably can't do likewise -- the Cuban account frozen in the United States is dwindling.

But even so, the award Friday in state court makes for a pointed political statement: It was five times more than the damages Suárez and Del Pino Jr. sought.

''I was flabbergasted,'' said Del Pino Jr. minutes after the verdict was announced in the courtroom of Miami-Dade Circuit Judge María Espinosa-Dennis. "I kept thinking why did they give us so much more?''

In fact, one of the jurors told Del Pino Jr. as he walked out of the courtroom: ``It was not enough.''

All of the jurors declined requests for interviews, but one -- Thomas Crews -- explained briefly that the high award was a message.

''Basically, all of us decided that we all wanted to send a message to the world that countries don't mess around with U.S. citizens,'' Crews said.

Experts say it will be nearly impossible for Del Pino's children to collect the award because funds in a frozen Cuban bank account in New York almost exhausted.

Most of those assets identified by the Treasury Deparment were paid out in the Brothers to the Rescue case and in two other Miami cases. Those involved the Anderson family, which received $47 million, and the Weininger family, which got $24 million.

Miami attorney Joseph DeMaria, who is representing the Anderson family and another Miami resident in a separate Cuban case, said: "We are facing more resistance in our efforts to collect on these judgments.''

DeMaria warned that Del Pino's children will also face legal obstacles, because the death of their father in 1977 occurred five years before the State Department placed Cuba on a list of state sponsors of terrorism -- a designation that opens the island nation up to liability.

''The timing of the case raises legal barriers that they will have to overcome in seeking to enforce their judgment,'' he said.

NO RELATIONSHIP

Though the central character in the case, Del Pino Siero, bears the same name as that of former Cuban Gen. Rafael del Pino, who defected in 1987, there is no relationship between them.

Del Pino Siero was born in 1926 in Havana but moved to Miami during World War II when he became a citizen and joined the U.S. armed forces. He later returned to Cuba to study law and ended up a classmate of Castro's at the University of Havana.

The two were so close that in 1948, they and other Cuban students traveled to Bogotá, Colombia, to attend a summit meeting of Western Hemisphere leaders that ended up being disrupted by one of the worst riots in Colombian history.

The uprising came in response to the assassination of Colombian presidential candidate Jorge Eliécer Gaitán. Evidence has emerged since then that Castro participated in the rioting. It is not clear if Del Pino Siero did as well.

Later, Del Pino Siero's family said, he traveled to Mexico intending to join Castro aboard the yacht Granma, whose landing began the Cuban revolution. Instead, he broke with Castro in Mexico.

''He noticed that there were Russian KGB there,'' said Del Pino Jr. "So right then and there he backed off and broke away from Castro.''

Del Pino Siero returned to his home near Miami International Airport and -- after the triumph of the Cuban revolution on Jan. 1, 1959 -- he began flying small planes into Cuba to smuggle out anti-Castro activists.

During one such ''extraction flight,'' Del Pino Siero was captured. The lawsuit filed in December 2005 in Miami-Dade Circuit Court alleges he was set up by a Castro "agent and spy.''

''Rafael del Pino agreed to fly to Cuba and when he arrived in Cuba, Fidel Castro's military was waiting for him and a gun battle ensued,'' the lawsuit says. "Rafael del Pinio was shot and sustained injuries and was immediately imprisoned by the Castro regime.''

Though he survived, he did not recover fully -- allegedly because he did not receive adequate medical care, his family said. He was sentenced to 30 years and died in the Combinado del Este prison in 1977.

Cuban officials have said he hanged himself. But the lawsuit says the Cuban government "intentionally, unlawfully, and with complete disregard for human life, tortured and killed Rafael del Pino by hanging him.''

The civil trial began Wednesday. The Cuban government was served with court papers but chose not to be represented in the courtroom.

The trial ended on a highly emotional note: Suárez, Del Pino Jr. and their attorneys -- René Palomino and Jorge Borrón -- cried openly in front of the jurors, who showed no emotion.

LETTER FROM 1969

The tears came when Borrón, in his closing argument, read from a letter that Del Pino Siero wrote from prison to Suárez in 1969 promising to buy her ''many presents,'' particularly a piano she had wanted since she was a little girl.

''My darling daughter,'' Borrón read, "I am happy to find out that you went to the beach and to the Seaquarium on your vacation. . . .''

Del Pino Siero went on to recommend that she buy ''good coats'' because she was planning to visit New York in the winter. The letter ended: ``Kiss, kiss, kiss, from your dad who blesses you.''

Borrón was openly sobbing while reading and had to stop several times to compose himself.

He ended his statement saying: "Ladies and gentlemen, this is Rafael del Pino speaking from the grave.''