On May 20, 1902, Cuba marked a significant moment when its flag symbolized independence for the first time. Yet, after more than a century, many would argue that true freedom remains elusive for the Cuban people. With past administrations’ approaches varying from inaction to ineffective responses, President Trump was distinct in recognizing the Cuban regime as a genuine threat to the US, aiming to tackle it decisively.
This failure over the years isn’t just unfortunate for Cubans; it’s a missed opportunity for the US too. The communist government in Cuba has been labeled a state sponsor of terrorism and has carried out significant espionage against America. Additionally, it has served as a nexus for illegal drug trade, affecting communities far from its shores.
Why has such a small nation, enduring a communist rule for 66 years that struggled to maintain basic infrastructure, been allowed to create such issues for a global superpower? It seems, in many ways, that the US turned a blind eye. One could argue that the most prosperous nation in history could have tackled the Castro problem ages ago, but there was a troubling lack of political will.
Take a look at the historical record: John F. Kennedy’s actions at the Bay of Pigs, Ronald Reagan and George Bush treating Cuba as a secondary issue during the Cold War, and Bill Clinton’s reluctant acceptance of the Helms-Burton Act under congressional pressure. George W. Bush seemed stuck in the status quo.
For too long, American presidents stayed inactive about the Castro regime, while Barack Obama took a contrasting approach, attempting to engage with it.
From 2014 to 2017, Obama’s administration pursued what many see as a reckless engagement shift in U.S.-Cuba relations. The reopening of the embassy, resuming flights, and the influx of wealthy Cuban-Americans enjoying privileges unavailable to regular citizens exemplified this misguided strategy. The assumption that opening up Cuba would foster reforms turned out to be misguided. The approaches faced harsh criticisms as the regime continued to suppress dissent and control essential resources.
Then came Donald Trump.
In January, the world witnessed a decisive move by U.S. special agents who successfully targeted Cuban security personnel linked to Maduro, illustrating that America could act decisively again. Trump’s strategy exerted substantial pressure on Venezuela in a remarkably short time, leading to similar strategies aimed at Cuba.
Cuba continues to rank as a state sponsor of terrorism. Recent measures, including the Cuba Restricted List and the reactivation of the LIBERTAD Act’s Title III, have intensified these pressures. With ongoing actions against key figures and entities in Cuba, it’s evident the narrative is shifting.
Despite some voices from the Obama administration urging for a relaxing of sanctions, many see these individuals as the architects of past failures. Their policies had detrimental effects, enriching certain groups and contributing to waves of immigration, which we are still navigating today. There’s a sentiment that there’s no obligation to retry a failed approach.
The potential for a new Cuba mirrors the successes found just a short distance away in Florida and across the Caribbean. There is a vision of everyday Cubans owning businesses, publishing freely, and having the capacity to influence their governance—something quite distinct from the current regime.
Trump stands out as the first president willing to classify the Castro regime as a legitimate threat, and with the right team in place, aims to conclude the tyranny in Cuba. His administration indicates that, over a century after the Cuban flag first represented an independent nation, there is hope that it will soon symbolize freedom.





