As a new, allegedly more humane government takes hold in Syria, American policymakers face a familiar temptation: To embrace a fresh face that promises stability and reform after years of chaos and bloodshed. But history warns us against such hopeful naivety.
In 1959, the United States welcomed Fidel Castro with more than a small dose of optimism, mistaking revolutionary fervor for democratic potential. That mistake proved costly. Today, as Syria reconfigures its political order, we must not forget the hard lessons of Cuba’s transformation into a Cold War adversary.
When Castro marched triumphantly into Havana, effectively replacing the American-backed dictator Fulgencio Batista, many in Washington viewed him as a charismatic reformer who would restore dignity and justice to the Cuban people. Initially, Castro downplayed his Marxist ideology, assuring the world that his revolution was rooted in nationalism and anti-corruption, not communism. The US extended diplomatic recognition and even offered some economic support.
Americans were curious. I’m old enough to remember Edward R. Murrow and his TV show Person to Person. Each week, Murrow would interview someone whom he thought his viewers would be interested in learning about. Guests ranged from singers to actors to politicians. In February 1959, the guest was Fidel Castro.
During the interview, which took place with Murrow in New York and Castro in his apartment on the 23rd floor of the Havana Hilton, Castro appeared to be wearing pajamas. He spoke of his mother, whom he hadn’t seen in four years, that he was not a communist, and that he hoped to be in the United States soon.
His son, Fidelito, who attended public school in Queens, New York, for a while, was introduced holding a puppy that was given to his father as a present. Hugging his son, Castro came across as a real family man.
Within a year of his accession to power, however, the reality emerged. Castro consolidated power, silenced dissent, “disappeared” opposition, and aligned Cuba with the Soviet Union. Land reforms masked wholesale expropriations. Promises of democratic governance gave way to authoritarian rule. A nation once seen as a neighborly partner became a staging ground for nuclear brinkmanship in the 1962 Cuban Missile Crisis.
Parallels between Syria's al-Sharaa, and Cuba's FIdel Castro
The parallels with Syria are not perfect, but they are striking. The civil war has left Syria a fractured and traumatized country. New leadership is arising in the guise of one Ahmed al-Sharaa. Already, his new regime is presenting itself as a modernizing force, a departure from the brutality of Bashar al-Assad’s rule. But we must remember: Revolutionary governments are not born with democratic values; they often acquire or abandon them in response to incentives and pressure.
We must ask: Who is Sharaa, what does he believe, and who stands behind him?
The 42-year-old has a documented history of affiliations with Islamist extremist groups, including offshoots of both al-Qaeda and, indirectly, ISIS. Known by his nom de guerre Abu Mohammad al-Jolani, Sharaa joined al-Qaeda in Iraq shortly after the 2003 US invasion.
He was captured by American forces and imprisoned at Camp Bucca from 2006 to 2011. Upon release, he returned to Syria and, in 2012, founded Jabhat al-Nusra, the Syrian branch of al-Qaeda, with backing from al-Qaeda’s central command.
In 2013, Sharaa resisted a merger between al-Nusra and the Islamic State of Iraq led by Abu Bakr al-Baghdadi. This refusal led to open conflict between al-Nusra and what became ISIS. Sharaa pledged allegiance directly to al-Qaeda leader Ayman al-Zawahiri, maintaining al-Nusra’s independence from ISIS.
In 2016, al-Sharaa announced that al-Nusra had severed ties with al-Qaeda and rebranded as Jabhat Fateh al-Sham.
The following year, he led the formation of Hay’at Tahrir al-Sham, a coalition of Islamist factions. HTS established a governance structure in Syria’s Idlib province, providing public services and collecting taxes, much like Hamas did in Gaza and Hezbollah did in Lebanon, but faced criticism for authoritarian practices.
In late 2024, HTS launched an offensive that led to the fall of Assad’s regime, and Sharaa became the de facto leader and was officially appointed president in January.
The Saudis and US President Donald Trump are responding to Sharaa’s courting of global legitimacy, offering a narrative of reform and stability to attract Western support. But we must remember: If we extend recognition or aid too hastily, we risk legitimizing a regime that could turn repressive, radical, or anti-American once firmly in power.
Moreover, the geopolitical stakes are high. As Prime Minister Benjamin Netanyahu has repeatedly said, “Israel lives in a tough neighborhood,” and Syria sits right in the middle of a region rife with Iranian influence, Russian ambition, and fragile neighbors like Lebanon, Jordan, and Iraq. If Sharaa decides, as Castro did, to align with America’s rivals, we could face another entrenched adversary in that “tough neighborhood.”
To avoid repeating history, US policy should be grounded in skepticism, not sentiment. Any diplomatic engagement must be conditional, incremental, and tied to verifiable actions: genuine power-sharing, protection of minority rights, disarmament of militias, and clear distancing from malign foreign actors.
The US must also engage with civilian society. The Cuban mistake wasn’t merely about misreading Castro; it was about ignoring the voices that warned of his true intentions. We cannot afford to make the same error in Syria.
In foreign policy, hope is not a strategy. As we watch a new regime take shape in Damascus, we must look to the past to guide the future. The ghost of Havana 1959 looms large. Let us not welcome another wolf in reformer’s clothing.
The writer is an attorney and the father of Alisa Flatow, who was murdered in an Iranian-sponsored Palestinian terrorist attack in 1995. He is the author of A Father’s Story: My Fight for Justice Against Iranian Terror and is the president of the Religious Zionists of America-Mizrachi.