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President Obama’s handshake of Cuban strongman Raúl Castro at Nelson Mandela’s funeral is no petty matter. Although some would argue that it was merely a polite gesture, it takes on added meaning when you examine the background of the two heads of state involved in the greeting.

The leader of the free world extending his hand, and a cheerful salutation, to a brutal dictator who has personally carried out the execution of hundreds of so-called “counter-revolutionaries,” is deeply disturbing. It is also a slap in the face to the Cuban exile community and the millions of Cubans who continue to suffer under the repressive regime of the Castro brothers.

As much as the White House would like you to think that the meeting with Raúl Castro was unscripted, it most certainly wasn’t. The world of modern diplomacy – and modern security – simply doesn’t permit such chance meetings. You are left to wonder why President Obama chose to shake the hand of an unrepentant murderer.

In the early years [Raúl Castro] was directly responsible for the execution of hundreds of “enemies of the state,” many of them innocent individuals, summarily rounded up and shot merely on the basis of rumor or innuendo.

— Raúl Mas Canosa

Yes, a murderer.

To understand the offense, one must understand a little more about Raúl Castro, Fidel’s younger brother and his successor. While Fidel was healthy, Raúl remained in the shadows, running the Cuban Armed Forces and maintaining a fairly modest profile. His low-key persona, however, was little more than an illusion. Raúl Castro was an avid participant in the Cuban revolution. In the early years he was directly responsible for the execution of hundreds of “enemies of the state,” many of them innocent individuals, summarily rounded up and shot merely on the basis of rumor or innuendo. Raúl’s penchant (and even enthusiasm) for executions is well documented in Brian Latell’s masterful book After Fidel: The Inside Story of Castro’s Regime and Cuba’s Next Leader.

In 1989, Raúl Castro even participated in the betrayal and subsequent execution of a man many considered to be his best friend, General Arnaldo Ochoa. Ochoa had incurred the wrath of Raúl’s brother Fidel, who accused him of treason and set him up in a show trial worthy of Joseph Stalin. Raúl sent him to his death, knowing better than to question his brother’s judgment. Other senior government officials were also rounded up and shot.

In addition to his role in executing hundreds of Cubans, Raúl Castro has come very close to being indicted by the U.S. government for his involvement with Colombian drug traffickers (in 1993) and for his participation in the premeditated shoot down of the two Brothers to the Rescue civilian aircraft (in 1996). Three of the four men killed in the shoot down were U.S. citizens.

Nevertheless, the President of the United States decides to shake the hand of a killer, a brutal dictator, and one of the last remaining despots of the 20th century.

Unbelievable.

And why was Raúl Castro at Mandela’s funeral?

In the late 20th century, Cuba and the Soviet Union allied themselves with African nationalist movements throughout the continent, anxious to extend their communist ideology. Cuba even sent tens of thousands of troops to fight against South African forces that controlled parts of Angola and modern day Namibia. Western democracies, including the U.S., supported the status quo, more concerned with stopping Soviet and Cuban expansion than they were with ending apartheid.

During that period of time, Nelson Mandela was a member of the South African Communist Party and supported violence and sabotage against the repressive and brutal South African government. He received assistance from the communists and openly admired Fidel’s Cuban revolution. Mandela even mimicked Fidel’s “History will absolve me“ speech at his own trial for treason in 1964. The outcome landed him in prison. During Mandela’s long incarceration, Cuba and the Soviet Union continued and even increased their support of nationalist revolutionary movements throughout Africa. Combined with increasing international condemnation, regime change ensued, including in South Africa.

There is a popular expression that states: “One man’s terrorist is another man’s freedom fighter.” The phrase has its origins in Gerald Seymour’s1975 thriller Harry's Game focusing on an Irish Republican Army (IRA) assassin and the British soldier sent to kill him.

For South Africans, and for many others, Nelson Mandela was a freedom fighter. To his credit, Mr. Mandela never engaged in wholesale murder, vengeance and retribution. He adopted violence (in the form of sabotage against government installations) only after repeated attempts at peaceful change had failed.

However, in the minds of many Cuban exiles, Nelson Mandela is no hero. Mr. Mandela sought and received the assistance of the Castro brothers in his struggle against apartheid. He praised their military intervention in Angola and Namibia. He continued to praise them and visited Cuba after his release from prison.

For Cuban exiles, myself included, Nelson Mandela is a terrorist sympathizer. Moral clarity requires no confusion.

And where does our President stand? Does he share Mandela’s Machiavellian belief that “the ends justify the means”? Does he believe that the sins of the Castro brothers must be forgiven? Does he think that by shaking the hands of a murderer he can wipe away a half-century of crimes against the Cuban people?

I hope and I pray that is not the case.