A Day of Reckoning for Raul Castro – Top 3 Takeaways – May 21st, 2026
Takeaway #1: A day of reckoning
The year and the month was... The Macarena was the #1 song in the country. Tupac Shakur was sentenced to four and a half years in prison for sexual assault. Art Modell fired Bill Belichick as head coach of the Cleveland Browns and announced that the team was moving to Baltimore. The Cuban government shot down two Brothers to the Rescue planes which were running humanitarian missions to Cuba from Miami. Fun fact on the Macarena btw, it was actually recorded in 1992 and released in 1993 by Los del Rio but didn’t take off until the release of a remix by the Bayside Boys (who also added some English lyrics). The year was 1996 and the month was February. Of course, my top takeaway today isn’t recounting Al Gore or any number of other stiff white guys attempting to do the Macarena at the DNC in ‘96. It is about what took place on February 24th of that year when the Cuban Air Force shot down two Brothers to the Rescue planes over the Strait of Florida which were in route to the island. Four Cubans were killed, two who were in exile, two who were American citizens. The Raul Castro approved strike was part of a Cuban government mission dubbed “Operation Scorpion”. Brothers to the Rescue was founded in 1991 and spent most of its first five years focused on rescuing Cubans, who were often in glorified rafts or substandard boats, seeking to flee Communist Cuba for the United States. However, by the summer of ‘95 their focus began to shift. The Castro regime had grown leery of the relative success of the Brothers’ rescue efforts so they cracked down on those attempting to leave the island in especially harsh ways – often with imprisonment. This led to the Brothers flying a flight over the island in which they dropped leaflets decrying the Castro regime. But little did the Brothers know that their organization had likely been infiltrated. One of the pilots, a former officer in the Cuban air force, turned out to be a Castro-regime operative who was believed to be tipping off the Cuban government about the Brothers’ next steps. On February 23rd, the day before the two Brothers planes were shot down, the Cuban operative flew back to Cuba and stayed. The next day when the planes filled with leaflets were in route to Havana, they were shot down. That’s the short-version story of what when down that precipitated yesterday’s indictment of Raul Castro in Miami yesterday. It’s the indictment that could mark the beginning of the end to the legacy Communist Castro regime. In the wake of Fidel Castro’s Cuban Revolution in 1959, a total of 1.7 million Cuban-born immigrants fled to the United States – with approximately 76% living in South Florida. Overtime the number has continued to grow through legal, and at times illegal immigration (following the end of the Obama administration's wet foot-dry-foot policy) with the Cuban-born population in the U.S. having reached 2.9 million most recently. Most Cuban exiles have families and property left behind making yesterday a particularly emotional day for many as the Raul Castro indictment came down at Miami’s Freedom Tower. So, the question is...
Takeaway #2: What happens now?
It’s natural to look at what took place in Venezuela only a few months ago with Nicolous Madauro and his wife having been captured by U.S. special forces and extradited to New York where they are awaiting a trial. But is a similar thing about to take place this time around? Maybe not, and here’s why. Raul Castro is 94 years old, Cuba is on the verge of collapse, and the government seemingly has no way to recover from the current crisis sufficiently to reestablish its communist controls. Before special forces jump in to confiscate Castro there will likely be an effort to use the indictment to negotiate an end to the regime. Leave on your own terms and live a potentially comfortable life in exile somewhere. Stay and be Maduro’d. The Trump administration tried to negotiate those terms with Maduro without success. Perhaps the credibility of the Maduro mission and the unsustainable conditions on the ground in Cuba will set the stage for a more favorable outcome this time? Either way yesterday was a day of reckoning and it figures to be a new day and era to follow for Cuba. As President Trump said back in March...
Takeaway #3: I do believe I’ll have the honor of taking Cuba
Taking was an interesting choice of words then. The implications are particularly interesting now. Whether that begins with “taking” Raul Castro to Miami to stand trial. Or whether that means an attempted effort to turn Cuba into a Puerto Rico styled commonwealth – where it maintains its independence, with its residents becoming U.S. citizens. That’s one of many possibilities that could come out of whatever is about to be. Secretary of State Marco Rubio, who is of Cuban descent, offered up this yesterday on what also just happened to be Cuban Independence Day: We in the U.S. are offering to help you not only alleviate the current crisis, but also to build a better future. First, we are offering $100 million dollars in food and medicine for you, the people. But they must be distributed directly to the Cuban people by the Catholic Church or other trusted charitable groups. Not stolen by GAESA to sell in one of their stores. President Trump is offering a new relationship between the U.S. and Cuba. But it must be directly with you, the Cuban people, not with GAESA. So now we’ll wait, watch, and see what will be. One thing is for sure; times are changing and from Venezuela to Iran to Cuba, some of the world’s worst regimes are changing.